If it feels like nothing you do online is working, you’re not imagining it. And it sucks because you’re probably running the same playbook that’s working for other people, and you’re probably running it better than 99% of the people whose content just seems to work.

The problem is that whatever playbook you are using is useless. Because the very concept of a playbook exists for a world that doesn’t exist anymore.

The market playbooks were built for is gone. And what’s going to sound insane until I prove it to you is that the only fix is the exact opposite of everything you’ve been told is good marketing. And all the stuff people are selling you l (all the move faster, post more, automate, let AI do the heavy lifting stuff) is only making it worse, not better.

The marketing that actually still works in 2026 is the marketing you do not want to do.

The Ratio

The Financial Times recently published a graph that shows mobile app production is booming. Which looks great until you notice that it also shows mobile app downloads are flatlining.

What this graph is actually showing you is something much bigger than mobile apps.

It’s showing you the hard limit of human bandwidth.

And it’s reminding you that no matter how much technology advances, there are only so many people with so many hours in their day, with so much money in their pockets, with only so much attention in their brains. Which means that after a certain point, the presence of good products, good apps, or anything good stops mattering, because good things can’t break into a public consciousness that’s already full, no matter how good those good things are.

We all know this.

Overwhelming choice makes us switch off.

The obvious parallel here involves. AI. As AI makes more things possible, brands are putting more good things out there. New products, improved products, you name it.

And it's a real problem. I know I can’t keep up anymore. Nor do I really wish to.

But it’s not just with AI companies or tech companies that this is happening.

This same effect is also happening to your emails, ads, content, and launches, which means every channel you touch is on the wrong side of one ratio:

And that ratio is the ratio of stuff to attention.

How We Got Here

Every channel, platform, or medium has the same lifecycle.

It’s born.

It lives.

It dies.

First, there’s a kind of frontier pioneer attitude about it.

The first newsletters were exciting when email was still exciting.

The first Google ads that were pennies a click, the first SEO, the first cold outreach, the first bloggers, course creators, and YouTubers. Doing these things was hard, but the hard work paid off. The early players won. But this is important: they didn’t win because they were the best, or because they were doing the best b`anner ads, newsletters, or YouTube videos. They were successful because when something is new, quality is not the metric of success. The metric of success is scarcity.

Then people copy the pioneers.

And the copycats get more modest returns. But modest or not, they still worked because there was still more attention available than there was stuff competing for it.

Then someone built a third-party tool that made creating courses, YouTube videos, or running newsletters easier. And just like that, the hard work that acted as a kind of moat for scarcity becomes obliterated. Now, anyone and everyone can take advantage of the platform. New people come in droves. And just like that, the platform dies.

AI just did that for everything.

But to be clear…

AI didn’t start the saturation.

It finished it.

How AI Poured Fuel on the Fire

Today, every barrier that held people back, writing being hard, design being hard, video being hard, producing at volume being hard, disappeared overnight. If, like me, you held back and didn’t jump in right away, you could literally watch it spread channel by channel and platform by platform in order of how easy it was for the machine to do the necessary work. Writing went first. First, it was X that got saturated and destroyed. Then the feeds, then the high-production channels. Then Instagram, LinkedIn, until here we are.

Thanks to AI, there is simply too much marketing being produced for far too few eyeballs. And nobody is talking about that or realizing it, which means everybody is still trying to use AI to run a playbook that assumes there is space in a market

But there is no space.

Because the result of all this marketing is that there is now so much “good” marketing that, in practice, there is no good marketing at all.

That’s your basic problem now. Because that’s also why your marketing isn’t performing.

The Saturated Man

Think about your own experience as a consumer. In the past, seeing something that looked interesting in your feed was rare. Today you've probably scrolled right past similar things because you can’t be bothered. Or worse: it looks so good that it’s probably just someone using AI to manipulate you. So, in other words, it’s so good it must be bad.

This is the response of a saturated human. When a person becomes overstimulated, skepticism becomes the default. And the only thing that can override that skepticism is some inbuilt form of trust, which in practice means attachment to a name you already know, like a brand, a creator, or an influencer you’ve already decided to trust.

But faced with this new unfilterable deluge, people are not filtering harder. They’re too exhausted for that. They are retreating to a tiny, closed set of trusted sources. As a result, their media diet is also shrinking. If they subscribe to a newsletter, they are only subscribing to one or maybe two newsletters (thank you, by the way). Or maybe just two creators. Maybe a few podcasts. And that is the customer avatar your marketing is trying to break into right now.

The natural response to all this is, of course, to produce more.

More posts.

More emails.

More campaigns.

Automate everything.

Let AI write the drafts, generate the images, schedule the calendar.

If reach is down, increase volume.

If engagement is down, increase frequency.

If the algorithm changes, feed it more, buy ads, or add another layer to the funnel.

It is also, historically, the wrong approach.

You Are Making It Worse

Every templated LinkedIn carousel, AI-generated newsletter, or batch of “authentic” content produced at scale, basically every additional post you automate to combat saturation, adds to it.

And that is because you are now competing on volume in a game where volume is the problem.

Which means you are not being crowded out by better marketing. You are being crowded out by the sheer influx of more marketing. And so, adding more of your own does not solve this. It accelerates it.

This is the fundamental hole in most people’s brains right now.

But the answer to this isn’t to do the opposite either.

And I understand the impulse. Nothing would be easier than to say: “Well, AI ruined everything. So let’s throw it out and go back to writing by candlelight.”

But that’s not the answer either. Because you will lose that battle. AI is not going away. Which means the question is not whether to use it. The question is what you use it for.

The Counterintuitive Fix (And the Whole Point of This Newsletter)

So today, most people are either using AI to produce more or choosing not to use AI to produce less. But very few people are using AI to think. And if you look carefully, those are the people who are killing it.

This is the only shift that matters right now.

When everyone has access to the same tools, the only thing that can separate you from the crowd is how you think (about the tools, but also how you think in general). And this is extremely important because thinking is compounded (that is the whole problem with using AI to skip the thinking, by the way).

Which means the blank page is not an obstacle. Thinking happens because you sit down to write. It does not happen, as many people believe, before. It happens with the generative friction that occurs between what you know and what you can express. That’s where the real work happens. That’s also where your voice lives. Because that’s where the idea that nobody else could have comes from.

And so when you remove that friction, you don’t free yourself. You actually strip yourself. And you end up producing worthless content.

But if you actually look for friction. That is, if you actually create marketing that is hard to make, you end up making something else.

This is the history of all marketing

This is also hard.

It takes longer.

It produces fewer posts.

And that’s exactly the point.

Do The Hard Thing

Everyone who started in marketing after 2010 has basically been trained to think of marketing as something that should either be free or cost as little as possible. And not just free but easy to make, ship, and scale. This was the promise of social media vs print and TV. And ever since digital marketing and social media took over, we have been taught that efficiency is the goal and that friction is the enemy, and that the only way to win is to remove every barrier between you and output as much as possible

But friction was never the enemy in marketing. As a matter of fact, when it comes to marketing, friction is not just necessary to create great creative; it is also a filter because it forces us to focus, interrogate our ideas, and commit to what matters. It also, by the way, protected customers from being hit by 400 annoying messages before lunch. And, more importantly, when things started to get noisy, the friction also protected us from adding to the noise. Because when something remained hard and stopped performing well, we just moved to another platform where it would perform better. That’s how creative advertising moved through cycles of creativity.

And this is exactly where all marketing is right now. Except it’s happening on a scale we never imagined, and it’s also happening everywhere. Which means it doesn’t matter what platform you are on. What used to work doesn’t work anymore. Because everyone can do what you have been doing. And everyone can do it consistently, and some who would have never done it before can even do it well.

Which means the only thing left to do, the only way to make your marketing start working again, is to be willing to do what nobody else will. Luckily, it’s never been easier to figure out what that is, because nobody else is willing to do anything hard or that requires thinking, innovation, or risk.

So here’s a test you should apply to any marketing idea you have from now on. Before you launch anything, ask yourself:

Would you still do this if it cost 10 times as much as it does?

Would you still do this if it took 10 times longer?

If the answer is yes, that means you find it valuable enough to justify the discomfort, which means there is probably scarcity in what you are thinking about doing.

If the answer is no, then whatever you are trying to do is cheap, easy, and probably something everyone is doing, which isn't necessarily a bad thing, but it does mean you need to approach it with the understanding that you get what you get and you can’t get upset.

WARNING: If you dedicate yourself to doing the hard thing and you honestly apply this test to your marketing, it will probably kill most of what you are planning to do right now.

And that’s good. Because what survives is the stuff that’s going to work.

And not just work because of the new approach, but also make all your other traditional and crowded marketing efforts work better.

I know this because I wasn’t planning on launching my Copy Hunter course right now. Mostly because it required doing things in a new way, a new way of thinking about how to sell a product. But as soon as I decided to do it and started marketing it, all my other marketing endeavors started working better as well.

Not only that, people have started doing unsolicited marketing for me, like the following review that was left as a comment on one of my LinkedIn posts:

Dear Justin

Your Copy Hunter’s Field Guide has helped me tremendously. I’ve been struggling with copy for ages. I tried gleaning from The Boron Letters, Ogilvy, John Caples, Sugarman. Tried Storybrand, Cashvertising, and online writing guides. Couldn’t get my head around any of it. AI helped a bit, but I was quick to recognize its patterns and wrestled with trying to make it sound like me. Copy Hunting has been the only thing to give me a clear and effective way to write and edit my work… and I’m only on Hunt 13/14. So I’m out hunting for commas and semicolons today. Even though I don’t remember the last time I used a semicolon. Can’t wait to get through the rest of the modules. You make writing fun. Thanks. - Mike L.

By the way, the whole idea of Copy Hunting is actually based on the philosophy of doing the hard thing. It consists of 52 hunts that you (not AI) run through your copy, promising to not only make it sound more human but also more persuasive and unignorable than 99% of the copywriting out there.

By the way, 38 of the 52 Hunts have already been released. Use the code PRESALE to get an unreasonable discount. Learn more here.

The Hardest Part About Doing Hard Things Is Getting Started

Before your next piece of content, spend 20 minutes without AI and write down 5 different ways you could market your product or service that you are not doing now.

Then rank them from easiest to hardest.

Then circle the hardest one.

Then open AI and use it to help you try and actually create a plan for doing it.

Have it create a plan where you tackle just one thing a day or week that gets you closer.

- Justin Oberman
Follow me on LinkedIn
My store

Subscribe to OberThinking for one essay a week on how to think differently in a world where everyone has the same tools.

Subscribe now

I once lost an account by being right.

It took four seconds.

A founder was explaining to a room (two co-founders, one investor, me) why his product was a category creator, and I said, pleasantly, that the category already existed, that three companies were sitting in it, and that one of them had raised sixty million dollars the previous spring.

Everything I said was true.

The founder thanked me (they always thank you). The invoice cleared. The engagement ended five weeks early. And I never heard from him again.

Cut to a year later. I’m sitting across from another founder (this time of an ad agency). I’ve made it through five rounds of interviews. This is the last one. It was supposed to be a courtesy interview. Based on my past work and the results of the paid project, I was told the creative director position was in the bag.

The conversation moved from where I went to school to my master’s degree, to my work, to different advertising philosophies, and to what I thought of his. After 15 minutes, he told me straight up he was going to hire me. The way I spoke over my glasses while talking about smart things reminded him too much of his ex-partner, who was apparently “Socratically annoying.” Those were his words, not mine.

I think about those moments more than I think about most of the work I’ve actually finished.

Being Smart Is Not Enough

The most beautiful woman you have ever seen owns a drawer full of face paint. Not because she needs it, or because other women with less beauty will do the same. But because she understands that it’s not just her beauty (inner or external) that matters. She understands that the artificial packaging matters too, if not more.

This packaging has many names.

In the past, I have covered it as showmanship, branding, publicity, and style. Whatever you call it, what I am talking about is the shameless business of paying attention to how people see you and understanding that being skilled or smart is not enough.

It’s nice to think that people judge us, like us, follow us, engage with us, or want to work with us based on our ideas alone.

But even the great philosophers relied on a certain level of artifice to get their ideas to the masses.

The philosopher René Descartes is famous for saying “I think, therefore I am.” But to make sure people got that far in his Meditation, he was one of the first philosophers to write in their native language rather than Latin.

Your intelligence (or skill or talent) is not unimportant. It is just not the thing people hire you for (even when they say it is). This is because it’s what people use to justify their relationship with you. It is what people point to afterward when explaining a decision they made for entirely different reasons. But of course they can’t tell the board that. They tell their board you were the sharpest mind available, and that can be said with perfect sincerity.

So, be good at what you do. Be great at it. But also understand that your greatness is not the reason anyone will choose you.

Which brings me to the unpleasant part.

What Happens if You Ignore This Advice

You can outshine your audience, client, or boss in many things. You can be richer than your client, and he’ll ask you for a stock tip. Be better-looking, and he’ll take you to dinner. But if you are smarter than them and you let it be known to them that you are smarter than them, either in the way you talk or speak or demonstrate, and you have committed the one offense for which there is no absolution, because you have not taken something from him, you have taken something from his picture of himself.

This is true of every class of people, by the way. But especially among the more powerful, because the more powerful someone is, or thinks they are, the less they can afford to let someone be seen as smarter than them.

Powerful people (or people who perceive themselves as powerful) want to be helped. They just don’t want to be surpassed, and they especially do not want to be surpassed for free, in front of witnesses, by a vendor.

The way that smart people unconsciously do this is simple enough to both spot and fix.

For example, smart people tend to offer unsolicited advice. As I mentioned above, one should be careful about how much they outshine their audience or client, even in areas where they are known or hired as experts. To do that about things outside that area of expertise will pretty much always be seen as meddling and met with the opposite of what a smart person intended.

Smart people should learn to avoid offering unsolicited advice when they can help it. But if you find yourself in a situation where it is necessary or can further advance your career or help the job at hand move along more successfully, then you should make sure that such advice arrives as a reminder of something they have “forgotten,” never as something they never knew.

All of the above are merely table manners.

Online and on social media, it can get worse because it can turn people off before they even reach the point of becoming a client.

There Are Only 7 Ways to Be Smart in Public.

Here are 7 Arts a Smart person must not only learn, but internalize if they are going to be successful as an online content creator.

1. The Art of Embedding Your Unique Ideas Into a Validated Topic of Interest

Smart people have genuinely unique ideas. That is why smart people are worth reading. But people (especially many people) don’t generally like unique or unusual thoughts. As a matter of fact, unless carefully created, unusual thoughts, aimed at a general audience, do not land as “insights” but as accusations, either because they imply that a person’s common belief is wrong or they imply that the reader was not smart enough to realize this themselves, and while people will forgive an attack on the things they are interested in long before they forgive an attack on their wisdom and intelegence. By the way, the offended come from both ends: those whose minds you are trying to change, as well as those who already agree with you but are offended that you are treating them as not knowing.

The trick here, as I talked about in a previous newsletter, is to frame our unique ideas around validated topics people are interested in. You pull them in with a validated topic and offer your unique take on it.

The good news is that you do not have to guess which subjects those are. Somebody has already run the experiment and even built a platform to help you discover and save them.

The key is to look for people’s outlier content. An outlier is a piece of content that dramatically overperformed the creator’s own baseline (I’m talking about roughly five times their normal numbers). It is not the same as a viral post from a big account. I am not talking about a creator who averages 400,000 views and gets 500,000. I’m talking about a creator who averages 900 views and gets 8,000 on a particular post. That is validation.

You could find these posts by hand. You could scroll through a hundred creators, note their averages, flag the posts that broke the pattern, and keep a spreadsheet.

I use a platform, Eden, tool that does so much, but one of the things it does really well is that it indexes creators and lets you filter an entire body of work by outlier score, so you can search a topic and see only the posts that beat their author’s baseline by three or five times. Last week I gave this away as a Claude skill. Install it, connect Eden, paste a draft, and Claude runs the hunt for you: it works out what the piece is promising, searches Eden for eight to fifteen genuine outliers on that promise, identifies which packaging mechanism each one is using, and hands you ten options with the source post attached to each so you can see the receipt.

To try Eden yourself, click here.

2. The Art of Thinking With the Few and Speaking to the Many

This puts smart people in a tough place.

The uniqueness that makes him or her worth reading is precisely the material that makes him or her unreadable. It’s also bewildering because amongst his peers, his unique thinking is celebrated. So he cannot understand why it gets crickets from everyone else, while the same idea, but tied to a milder observation about mornings, got 40,000 people to celebrate.

One of the hardest things for smart people to come to terms with is that what you say to the many and what you say to the few smart people like yourself are not the same thing, just delivered at different volumes.

They are different.

In public, smart people must learn how to speak in the common tongue using common ideas, however dull they may be, because the common tongue is the price of admission. This doesn’t mean you shouldn’t share your most controversial ideas with the masses. It just means that if you do, you must learn to deliver them in the language and with the interests of the common people. The straight, unique, and controversial stuff you must save for your inner circle as well as the people who bought the course, joined the group, took the call, and made themselves the few by an act of choice.

A good motto for smart people to help them remeber this: “Thought is free. Speech is invoiced.”

3. The Art of Giving It All Away But Explaining Nothing

Truly smart people don’t just share to show off. They share because they genuinely care and want the people around them to have the same knowledge they do. So they tend to give people all the information. This is always a bad idea.

First off, over-explanation reads as insecurity. Secondly, even if they are eager to accept new ideas and are not offended by them, people cannot tolerate too much information at once. Especially if it is new.

But the real reason you should learn how to resist the urge to explain too much is that unique ideas are more easily accepted when the person who hears them feels like it was they, and not you, who came up with them. This is true, by the way, even if they know it was your idea. All a person needs is the feeling of coming up with a new idea themselves to help them along with it. But when you overexplain it, you rob the reader of the pleasure of arriving at your conclusion themselves.

4. The Art of Staying in Your Lane

Smart people need to learn how to show up and be present where they were invited, on the subject they were invited to. Nowhere else. As I mentioned before, the consultant who has an opinion on everything is seen as meddling and will eventually be let go. The same is true of someone who posts about many things outside the areas they are known for. This is especially true on platforms like LinkedIn.

This is very hard for smart people because they want others to know everything they know and all the ways they can help. And they can. They just can’t make the strength of their general knowledge the main thing. It’s better to let people discover that themselves. Which leads me to the next point.

5. The Art of Underpromising and Overdelivering

Smart people are very confident. They therefore like to promise the moon right from the start. This is always a bad idea for two reasons. The first is that it sets you up for a greater chance of failure. And secondly, it makes you look pompous and once again meddling. This is also true of the way smart people need to show up online. It’s O.K to talk about your successes and demonstrate how you achieve them. But, once again, you only want to talk about success as it relates to the area you are focusing on. And even then, you always want to frame that success in the circumstances in which it exists.

In other words, smart people need to learn how to promise less than they are. Let the first engagement reveal a floor, and let every subsequent one reveal that it was a ceiling you were standing on.

6. The Art of Mixing Things Up

Once again, this is a result of smart people believing that their intelligence or talent is enough. And I know this is going to sound like I am contradicting myself here. But I am not. Earlier, I said you need to learn the art of staying in your lane, and now I am telling smart people to mix things up. To see that these are not contradictions, you need to understand that expertise ages alongside its own fame and how audiences that once admired you in March can easily get bored of you by September. But not because you got worse, or because the world has changed. But simply because you stayed the same.

Maybe you stayed the same in your approach, your manner, and your style. Maybe the time to reveal a little more had come (because the audience had become more sophisticated), and you stuck to the old rule.

Whatever the case, it is important for smart people to remember that mediocre novelty beats familiar genius every time. You don’t need to change what you are smart about, but you may need to change the form or frame you present it in and, like Picasso, come back with a new style or period.

7. The Art of Losing an Argument

One major difference between smart people and ordinary people is that smart people like to be proven wrong. One major similarity between smart people and ordinary people is that they prefer to be proven wrong privately. Smart people love to defend themselves online in the comments. And they can do so with more force than most people.

Which is why (for reasons stated above about how one's intelligence can make people feel) smart people must learn to repress the urge, even when the evidence is on their side. If you are correct, your position will be recognized later by everyone without your help. But your graciousness and politeness during the debate will be noticed immediately. Stubborn insistence loses more than winning gains.

A smart person needs to remember that there are people so committed to their own view that arguing with them costs you twice, once in the fight and once in the consequences, and against those people, your judgment can hold firm while your *will* stands down.

***

I would like to tell you I have mastered all of these arts.

I haven’t.

As a matter of fact, I am pretty sure this newsletter violates at least three of them (and one twice). But perhaps that is also an art that smart people must learn. The Art of When to Break the Rules.

In this case, I am assuming that anyone who subscribes to a newsletter called OberThinking is above average in intelligence. So in this case, I am practicing the art of number 2 (thinking with the few and speaking to the many).

Which makes the founder at the beginning of this newsletter right, by the way.

Not about the category, he was wrong about that.

But about me.

And that is why I also have no problem telling you that Callum Laing nominated me for Thought Leader of the Year at the 2026 Veblen Awards. In the nomination, he wrote that the problem I work on is low-quality automated writing, and that what I actually teach is editing or Copy Hunting, that is, putting a person back into what the machine hands you.

That is my public-facing job description. Which is why I don’t mind sending some of my inner circle to cast some votes for the hidden stuff ;-).

Voting closes tomorrow morning, 8am Pacific.

VOTE HERE

Justin Oberman

And instead of babbling on about what people think, I'm going to cut right to the chase.

Most people are afraid that their unassisted thinking is not good enough.

That is the actual reason.

The fear.

And boy, oh boy, do I get why..

It makes sense.

You have a lot to do, and the machine, like a warm, smiling friend, is always there. And ready. And confident.

It does not stare at the screen for twenty minutes, producing nothing. Or write three sentences and delete them. It has never had the experience of reaching for an idea, grasping it, and finding it ugly or dull.

It just…

humms along…

And when you compare what it does to your own slow, messy, unassisted thinking and drafts that go nowhere, the machine looks like the smarter choice.

So you use it.

Not out of laziness but out of fear.

That is the real reason everyone's face looks the way it looks.

Not because of too much AI.

But because of too much fear.

What The Fear Is Actually Protecting You From

The fear of your own unassisted thinking is not irrational.

Your first draft is probably nowhere near as polished as the machine's first draft.

Your unassisted ideas have human gaps. Your natural writing style, if you have one, will never be as consistent as the machines.

All of that is true.

But that's also what makes you great.

Because every person I know who has produced work that has genuinely stopped people has done so by going through those inconsistencies and uncomfortable gaps.

Especially when you do not yet know what you think.

You know…

Where you write something, and it is wrong, and you know it is wrong, but you keep writing because you know the right version is somewhere on the other side of the wrong version.

That’s where the work that matters comes from.

As we all know or have been told by now, AI does not go through any of this.

AI goes around it.

The 30-Day Recalibration

As always, I am not telling you to stop using AI. I use AI constantly. The protocols in this newsletter are built on AI.

Nor am I saying that your unassisted thinking is always better than AI-assisted thinking.

It is not.

For certain tasks like research, structure, and generation of first drafts, you will heavily edit; AI is genuinely useful, and the output is genuinely better.

But what I am saying is this:

You do not actually know how good your unassisted thinking is. Because you have not tested it recently. Or at all. Because you went from occasionally using AI to habitually using it, and pretty much stopped finding out what you can actually do without it.

So the 30-day calibration behind the paywall is not a detox. It is more of a measurement.

If you are a paying subscriber, you are going to spend thirty days finding out what your unassisted thinking can actually produce. And you are going to find out on a specific type of work, in a specific context, so that you have real data about where the machine can make you better and where it is getting in the way of something valuable you already had.

Subscribe now

I think that data is the most useful thing you can have right now.

The Setup

The calibration protocol behind the paywall this week is a thirty-day structured experiment.

Please don’t think of this as a creative challenge or a productivity hack.

It is, as I mentioned before, a scientific measurement of your own thinking designed to give you specific, actionable data about where your unassisted mind is stronger than you believed, and where AI genuinely adds something you cannot produce alone.

It runs in three phases.

Each phase is ten days.

And each phase has a specific focus, a specific measurement, and a specific question you are trying to answer.

By day thirty, you will know something about your own thinking that most people never find out.

By the way, if you want to understand why you are still reading this, then you need to understand that only part of the reason is that you find it interesting. The other reason is that after I write whatever I write, I go through my drafts, hunting for places to make the kinds of improvements that keep people reading. If you are interested in that kind of thing, then you will probably be interested in my Copy Hunter course. 28 hunts have already been released. Use the code PRESALE to get the course for more than half of what it will be when it’s finally finished. [link]

The 30-Day Unassisted Recalibration Protocol

So there are two parts.

Part 1 tells you exactly what this is all about, how to run it, and what to measure.

Part 2 is the AI-guided reflection session you run at the end of each phase to process what you found.

PART 1: THE CALIBRATION

What is this:

A thirty-day structured experiment in three ten-day phases. Each phase produces a specific type of output, like a post, a newsletter, or a piece of strategic thinking without AI assistance. At the end of each phase, you measure what you produced against your AI-assisted baseline and answer three specific questions.

Again, the goal is not to produce better work without AI. The goal is to find out what your unassisted thinking actually looks like so you can make deliberate decisions about what to hand off and what to keep.

What you need before you start:

A baseline.

Before day one, collect five examples of your best recent AI-assisted work. These are your control groups. Keep them somewhere you can reference.

You will also need a journal. You will write in it for ten minutes at the end of every day. It doesn’t matter if it’s physical or digital. The prompts are below. Personally, I do all my protocol journaling and AI work this way in Eden. Here’s why:

The problem with running a calibration like this in a regular notebook or even a note app or a chat window is that the insights disappear. You write something on day four that matters, and, if we are being honest, by day fourteen you have forgotten it. And by day thirty, when the reflection session asks you to find the pattern, you are scrabbling and guessing rather than reading.

Eden solves this because it is built to capture raw thinking and store it in a way that is searchable and retrievable, and it can connect whatever you write one day to another day, and even to other ideas you collect from all over social media or the internet.

When I run a protocol journal in Eden, every entry is a note that lives in my workspace. I can search across them. I can see them side by side. I can even ask Eden to surface the ones that are related before I sit down for the end-of-phase reflection session. Eden is built on AI, but the AI part is really just there to help creators find the patterns in their own thinking instead of generating thinking for me. It’s the only AI tool I have found so far that does this.

Eden also lets me store the outlier posts and writing samples I am calibrating against (the control group) in the same place as my journal. Which means when I want to compare what I produced on day twelve against my AI-assisted baseline, everything is in one workspace instead of scattered across tabs.

Another great Eden feature is the ability to schedule posts to multiple social media platforms.

I also like Eden for an unintended reason. It is pretty bad at writing stuff. Which makes me rely on myself more. But this is made easier because that is what Eden is designed to make easier.

So if you feel like you are dumber than AI, there is no faster way to realize how wrong you are than by starting to use Eden.

Especially if you start using it by running the reCollaboration Protocol below.

The free plan is enough to get started, but to understand its real power, I would definitely consider starting with one of the minimal spend plans.

Start here.

Besides that, you will also need to be ready to show up for thirty days because the calibration only produces useful data if you run it consistently. Missing days do not invalidate the experiment, but missing phases do.

PHASE ONE: THE ORIGINATION PHASE (Days 1-10)

Read more

There is a shrine in Mie Prefecture, in southern Japan, that has been around for about 1,300 years but has also never been older than 20.

That’s because Ise Jingu is not maintained in the same way most shrines are. It is rebuilt so that the buildings will be forever new and forever ancient, and forever original. What happens this:

A second plot of ground always sits empty beside the shrine. Every two decades, specially trained carpenters raise an exact new shrine on the empty plot out of cypress that was felled and seasoned for the purpose. At some point, the deity is carried from the old building to the new one at night. The old building is taken apart the next morning. Its timbers are sent to shrines around the country, where they start second lives as gateposts and crossbeams, etc. The vacated plot is then swept empty and waits for twenty years until the whole ritual is practiced again. The rebuilding in 2013 was the sixty-second.

I find this almost unbearably fascinating. Because, as I said in the newsletter I wrote about pen brands a while back, it draws you into so many questions about what something, anything, is. Just as the shrine is permanent, but the building is temporary, so is a pen brand, while the ink cartridge inside is replaceable. Which means that the permanence of something is or can be achieved not in spite of the impermanence but by means of it.

And in this case, it is even more powerful because the impermanent force driving the permanence is people. That is to say, Ise Jingu survives only because one generation of carpenters teaches the next what to do. And what makes it even more amazing is that they do that while doing the work. They don’t, in other words, write down a system which would mean that if, for some reason, the rebuilding of Ise Jingu were to stop, all that would be left is a very old and very beautiful building. But it would not be Ise Jingu.

I know it’s difficult, but try to hold onto that thought while reading what comes next because I am about to show you how this way of thinking about things also happens to be a very healthy way to not only think about everything you do, but yourself as well.

The one thing the internet has finally agreed on

If you strip away the arguing and dive into the data, there is a single doctrine that unites almost everyone publishing marketing and sales advice online:

Consistency beats intensity.

Show up daily.

Trust the compound effect.

These things take time.

So I used Eden to see what kind of consistency content actually travels furthest by looking at outlier posts (posts that did +10x the norm on the largest creator accounts). And the pattern is clear:

A clip of Joe Rogan telling out-of-shape men to start with five push-ups collected over a million and a half views and outperformed his own account by a factor of thirty-four.

A 40-year-old lifter condensed twenty-five years of training into two minutes: two focused sessions a week beat five mediocre ones.

A three-thousand-word sermon on the one per cent rule did twenty-three times its channel's normal numbers.

The reason content about consistency does so well is that it is right. That is what Consistency really is: one of the most important mechanisms for achieving anything. With the exception of dumb luck, nobody sensible questions it.

The problem is that consistency is usually discussed as a rate—the frequency with which you do the thing—so almost everyone hears “be more consistent” as a description of a method where you find a system, lock it in, and never deviate.

You know what I’m talking about: the 5 a.m. wake-up bros, the hook formulas, the three-part newsletter structure (AIDA, PAS, AIDGA, APAG), and let's not forget about content pillars or core values.

The carpenters at Ise are consistent as well. The thing they are consistent about, however, is the rebuilding. They are entirely unsentimental about the building itself.

All of which is comparatively easy to arrange when you are a shrine, but is considerably harder to arrange inside a working life, where the timing is left entirely to us, where nobody has swept a plot in readiness, and where we are almost never willing to let go of a thing while it is still working.

Nietzsche on the pleasure of parting company

Which is why I find it useful that somebody thought this through for individuals rather than institutions. The philosopher Friedrich Nietzsche is not everybody’s idea of a light read, but he was extremely good on this particular subject, and the useful thing he did was to stop framing it as consistency against inconsistency but rather as brief habits against enduring ones. And he loved the brief sort, because he thought them an invaluable way of getting to the bottom of things, “both their sweetness and their bitterness.”

His account of how it goes is uncomfortably honest. Something new arrives, and you believe, with total conviction, that here at last is the thing that will satisfy you permanently. While it is new, it nourishes and spreads deep into you. In a way, you become rather boring about it and mildly contemptuous of the alternatives.

I expect a good many of you can recognize yourselves in that description. How many formulas and systems have you held close to your heart and presented to other people as very nearly an article of faith? And how many of them did you keep until the day you quietly noticed they no longer served you, and let them go, not because they had come to disgust you but let go of them peacefully, so that the parting occurred (in Nietzsche’s phrase) “as if we had reason to be grateful to each other”?

Which is why the manner of the ending matters so much more than anybody supposes. Most of us do not part with our methods. We are eventually thrown out by them, at the point of failure, in front of an audience. And a thing you abandon in humiliation is a thing you cannot afterward go back and learn from, because you are too busy pretending you were never that person. So if we are being honest, ending on good terms is not just politeness. It is the arrangement you make for yourself in which you get to keep whatever the habit has taught you.

The man who was grateful for his own bad health

Enduring habits, on the other hand, Nietzsche could not tolerate at all. When one came near, he said, he felt as though “a tyrant had entered the room and the air had thickened.”

And I think I know why. It is not simply that he was a difficult man (though he was). It is that a habit held long enough stops being something you use and starts becoming something you are, and once it is there, it can no longer be assessed, because assessing it would mean assessing yourself. This is why the man who has been getting up at five for eleven years cannot discuss whether getting up at five is working. Or why the person who has been running the same LinkedIn strategy for years cannot discuss why it is really working.

It may be doing him an injustice, but there is something rather touching about a philosophy so precisely shaped to the life its author was stuck with.

Nietzsche had, it must be said, unusual assistance in avoiding all this.

He gave up his university chair at Basel in his mid-thirties on grounds of health, and spent the following decade moving between boarding houses in Switzerland and Italy with a trunk and a modest pension, chronically ill and more or less permanently uncomfortable.

He said he was grateful for the misery. But let’s be honest. A life that keeps going wrong leaves you with a great many ways out of anything that threatens to become permanent. And yet, and this is the part that tends to get left out by people who quote him in support of their own restlessness, he also thought a life with no habits whatsoever would be the worst life out of all of them because a life demanding perpetual improvisation would be a kind of exile from life itself.

The perpetual improviser, the person who says “just be yourself,” never commits to anything long enough to reach failure and so spends his or her entire career chasing one method after another.

We have the wrong things on long contracts

Which brings me to marketing or advertising or branding (both the personal kind and the regular kind)

Consider the models we use. Models like the unique selling proposition, positioning, the brand onion, the brand pyramid, the brand key, and the brand essence (which lived, if I remember rightly, in a small box at the center of the onion and was usually a single word such as “trust”). And then there are the more modern ones, like integration, the funnel, engagement, virality, purpose, and whatever we are calling it this season.

Each of these models was invented as a useful simplification, which was then, in turn, adopted with religious fervor, defended before clients, taught to students, and even made a condition of continued employment. And each was also eventually abandoned, sometimes with a grateful handshake but often with a certain amount of embarrassment, similarly to the way one quietly stops mentioning a friend who has been arrested.

I imagine that many of the things said about AI will go this way too.

I do not believe, however, that any of these models were wrong, but that they were all brief habits mistaken for enduring ones. Which means, ironically, that they deserved our total conviction while they lasted, because a model held half-heartedly teaches you nothing at all.

And in the same twenty years during which we clung to our onions, we also became extraordinarily casual about the one thing that genuinely needs to endure.

The only thing that ought to have tenure

Brands are not built in boardrooms; they are built, slowly and rather untidily, in the heads of the people who encounter them. As the advertising philosopher Jeremy Bullmore put it, people assemble them out of scraps and straws like a bird’s nest: a wrapper, a delivery driver, a call center, a remark from a brother-in-law, a poster half seen from a bus. A brand, in other words, is an accumulation of things.

And accumulations are undone very quickly by discontinuity.

Which means that a brand’s character (its manner, its tone, its way of behaving when nobody important is watching) is precisely the wrong thing to reinvent every eighteen months, and yet it is very often the first thing a new CMO or a person trying to keep their personal brand up to snuff does.

Which means we have it inverted. Our methods, which ought to be brief habits, are treated as doctrine. And our brands, which ought to be enduring habits, are treated as this year’s opportunity for self-expression.

Just to be clear, I don’t think this happens because anybody is stupid. I think it happens because changing a brand is visible, while changing your own model is not. At least that’s what people believe. Nobody was ever promoted for quietly retiring a framework.

Giving a model its term of office

If I were to offer anything practical (and I am always a little suspicious of anything that ends with instructions), it would be this:

Give every method, habit, or system you take on a term of office rather than a trial period.

What’s the difference?

A trial period implies you are hedging by keeping one eye on the exit, which guarantees you will learn nothing.

A term of office means you have your full loyalty, why you have it, and its authority is not up for debate. And at the end of the term,m it does not simply carry on. It has to be re-elected or sent home. And the burden of proof sits with you.

I think it is important to note here that the signal that a term has expired is not boredom because boredom usually turns up far too early for the wrong reasons and should therefore be ignored.

The signal that the term has come to an end is the moment you notice you are defending the model rather than using it. Or when you hear yourself explaining to somebody at a conference why it works, at length, with unusual warmth.

And if you judge that the term is over?

You don’t just destroy it.

The cypress at Ise does not burn.

It goes off to smaller shrines and remains useful. It just becomes useful in a role nobody originally designed it for.

That, I suspect, is what happens to a model you have honorably finished with.

The Unique Selling Proposition discipline you outgrew left you unable to write a sentence without cringing. The funnel you abandoned taught you that people arrive at things in stages, a truth that remains even though the diagram never was.

Which means that nothing you invested your time in believing is wasted. It is merely redistributed into judgment.

Which is much harder to name and sell than a framework. Which is why most people don't, and why I can do nothing more than write an essay about it.

Nietzsche, of course, would have understood all this perfectly. He knew exactly which habits to get rid of when.

The rest of us, it seems to me, might usefully ask ourselves how much of what we are currently defending is scheduled to be taken down and cleared soon.

Justin Oberman

p.s Want to know the secret about how I kept you reading to the end? Check out my Copy Hunter Field Guide Course. The first 20 to use the code PRESALE to get it for a fraction of the price.

June 12, 2026

In 1963, Howard Gossage won the Rover Car Company account (a small British outfit, modest budget, selling Land Rovers to a sliver of the American market).

His goal was to sell what most people viewed as a rugged, utilitarian vehicle to the upper-middle class.

And so, in typical Gossage style, the very first ad he wrote for them was not about the car. It was about billboards.

Now, please pause and consider the audacity of this.

Your first ad for a new client. A car company. And instead of showing the car, or talking about the car, or in any way attempting to sell the car, Gossage seemingly used the client’s money to continue a personal crusade against a medium that half the advertising industry depends on for its livelihood.

Which would be crazy, except that it was the client’s idea.

You see, this was not the first time Gossage, an ad man, attacked outdoor advertising either.

In 1961, he published an article in Harper’s Magazine arguing that billboards had no right to exist.

This was, to put it mildly, an unusual position for a person in advertising to take publicly. It would be like a sommelier writing an op-ed in a national magazine arguing that wine is mostly a con.

The Harper’s article was called “How to Look at Billboards,” and its central argument was devastatingly simple: outdoor advertising sells a commodity it does not own. What it sells is your field of vision. And it does so without asking your permission.

For those of you who have never heard of Howard Gossage, I envy you, because you now get the thrill of experiencing him for the first time.

Howard Gossage ran his agency out of a converted firehouse on Pacific Avenue (Engine Company No. 1, if you’re keeping track), where on any given evening you might find John Steinbeck nursing a beer, Buckminster Fuller explaining geodesic domes to nobody in particular, or Marshall McLuhan telling bad jokes. David Ogilvy, who did not agree with Gossage very much, called him “the most articulate rebel in the advertising business.” Jeff Goodby, decades later, went further, calling his work the best advertising ever made. Rory Sutherland says that “Gossage is the Velvet Underground to Ogilvy’s Beatles and Bernbach’s Stones; never a household name but to the cognoscenti, a lot more inspirational and influential.”

And Gertrude “Jimmy” McWilliams, Gossage’s counterpart at Rover, had a hunger for attention that perfectly matched Gossage’s gift for generating it. She understood (perhaps more clearly than Gossage himself) that the billboard ad wasn’t a distraction from selling cars. It was the best possible way to sell them. Because the ad did something that a photograph of a Land Rover in a muddy field could never do: it started a conversation.

The Fury of the Decent and the Respectable

The Board of Directors of the Advertising Association of the West, at its 16th anniversary convention in Los Angeles in June 1963, passed a formal resolution. It declared that the ad was “not a fair consideration of the merits of this respected form of advertising,” that it was “not in good taste,” and that it “fails in its presumed purpose of influencing public opinion due to the obviously prejudiced position taken by the advertiser.”

They then resolved to send copies of this resolution to all member advertising clubs, the Rover Motor Car Company, Gossage’s agency, and every publication that had carried the ad, urging member organizations to “individually voice their disapproval.” Advertising Age piled on. The industry closed ranks with the righteous indignation of a gentleman’s club that has just discovered a comedian at the lectern.

Despite the protests (or perhaps because of them), the ad also sold many Land Rovers. Senator Maurine Neuberger inserted that ad into the Congressional Record, which, if you ask me, is something that rarely happens to failed advertisements.

Even David Ogilvy wrote to Gossage with something rather different from indignation.

Gossage, characteristically, was delighted by all this. But it also gave him an idea for the next ad.

The Sincerest Form of Larceny

The instinct of most people trying to attract premium clients is to sand down their opinions. To be smooth, agreeable, inoffensive. To say what they think wealthy audiences want to hear.

Gossage did the opposite.

Howard phoned David Ogilvy and asked if it would be OK to parody the most famous car advertisement ever written.

Ogilvy’s Rolls-Royce ad, first published in 1958, had established a standard that every luxury car brand spent the next half-century trying (and failing) to imitate. The headline was a masterpiece of elegant restraint: “At 60 miles an hour, the loudest noise in this new Rolls-Royce comes from the electric clock.” Quiet meant money. Silence meant class.

Gossage asked permission to steal it, and Ogilvy, who evidently had a sense of humor that his writing style and philosophy of advertising did not always suggest, said yes. He even sent Gossage a signed proof of the original.

So Gossage ran a Land Rover ad in the exact same layout, the exact same typeface, the exact same unhurried, meticulous rhythm as the Rolls. The body copy was his own, naturally (he copied, as he put it, everything except Ogilvy’s writing style and content, dealing his own head in) but with a different headline. At 60 miles an hour, the loudest noise in this new Land Rover comes from the roar of the engine.”

Gossage’s Rover ads open with a genuine conviction that cost him something to hold publicly, and the people who shared that conviction (many of them, as it turned out, wealthy, educated, and deeply tired of being pandered to) recognized him instantly as someone worth paying attention to.

My point here is that not all premium audiences are looking for smooth. They encounter smooth all day long. Some are looking for someone who actually believes something.

So to sell Land Rover cars upmarket, he didn’t pretend that the Land Rover was a Rolls-Royce. He dressed it in the Rolls-Royce’s suit and bragged about being the opposite. Quiet was for people who never left the road. His car was loud because it went where roads stop.

Ogilvy was so delighted that he invited Gossage to dinner the night the ad came out. Gossage brought him a framed copy, and Ogilvy insisted on reading the entire ad aloud to Gossage, who (one imagines) sat there with the patient expression of a man listening to someone recite his own work back to him. Gossage inscribed it:

“To David — imitation is the sincerest form of larceny.”

Despite Ogilvy’s approval, Printers’ Ink, the now-defunct advertising trade publication, complained editorially that the ad was an “in joke” that didn’t do justice to the client.

It sold cars like crazy, though

What the Reprobate Ad Man Understood

Gossage followed these ads with a two-page advertorial split across two separate editions of the same magazine. You had to buy both issues to get the whole argument. Near the bottom of the second installment, he placed a boxed teaser: NEXT! “THE LAND ROVER AND CRIME.”

In August 1963, fifteen men pulled off the Great Train Robbery — the most audacious heist in British criminal history. They stopped a Royal Mail train at Cheddington, Bedfordshire, overpowered the crew, and vanished with £2.5 million in cash. The getaway vehicles: two Land Rovers and an Army truck. Nearly a week passed before a man out hunting for mushrooms near a lonely farmhouse at Brill, Buckinghamshire, noticed the top of a Land Rover protruding from a tumbledown outhouse among the trees and reported it to the police.

So naturally, Gossage had to turn it into an ad.

He noted, with the gravity of a Times editorial, that the four-wheel-drive vehicle clearly possessed latent virtues of interest to the prospective owner. He hastened to add that it was not Rover’s intention to suggest ways of picking up a large amount of extra money in one’s spare time. Rather, the opposite: to abet law and order by useful suggestion.

He then reported on the Great Train Robbery in lavish detail — maps, quotes from The Times, police reports, even the observation that the robbers had chosen Land Rovers not only for their rugged dependability but for their capacious rear doors, since when you are trying to load bags and bags of stolen banknotes in a hurry, you simply haven’t got the time to aim nicely; it’s not like darts. He observed that the police also used Land Rovers (though curiously, nowhere was it reported they employed them in hot pursuit of the brigands — perhaps their mistake). He covered a second robbery in Longfield, Kent, under the heading “LAND-ROVER STRIKES AGAIN.” And he addressed the inevitable objection from law-fearing citizens: “Why, decent, law-fearing people may ask, do you sell Land-Rovers to chaps who are going to use them to rob trains and banks?” His answer: they couldn’t always tell.

The ad ran over to the next page “(cont. on next page)” because the story was too good to contain. On the continuation, he noted that Rover had sold to the armed services of twenty-six nations, police forces of thirty-seven countries, desert chieftains, gold prospectors, titled persons (mostly for country use), and multitudes of nice families for skiing, beach buggying, and other pleasant things. With such a limitless range, one often didn’t know precisely how a buyer intended to use his Land Rover.

The robbers, it should be noted, did not get away with it. That Gossage got away with celebrating their exploits in a paid advertisement is testimony to his chutzpah and the Rover client’s remarkable nerve.

The ad highlighted the power and features of the Land Rover by showing how it was used to accomplish one of the most daring criminal heists in the UK. And as if promoting crime to sell a product wasn’t audacious enough, he cut off the full-page ad and continued it on the other side.

From Shooting Crime to Fashion Shoot

Because you need to feature the car sometimes, Gossage followed the Crime ad with perhaps the most perfectly executed sight gag in advertising history.

The Land Rover Concours d’Élégance Entry for 1964: a boxy station wagon parked before a neoclassical building inscribed HONNEUR ET PATRIE, with Rodin’s Thinker perched on the roof. “One imagines they’re worried sick over at the Brand X Limousine Division.”

The credits, where a fashion spread would list designers, listed other things, including ads and stunts he created for other brands like the “Pink Air” stunt for Fina Gas stations.: “Wicker work by Charlie and Nellie Bernhardi; White side walls by Pirelli; Lacquer job by Wade Looper (on overtime); Gold fine-striping by Bob Funke; Coach lamps by Cost-Plus Imports; Mink lap robe by Neiman-Marcus; Flower vases by Michelob; The Two Pink Carnations by Podesta Baldocchi; Silver flask in glove compartment by Abercrombie and Fitch; Pink valve caps by American Petrofina; Basic black Model 88 Station Wagon by Land-Rover; The Thinker by Rodin.”

Like the Ogilvy spot, it was parody so meticulous, so affectionate, and so deadpan that you couldn’t tell whether it was mocking the luxury market, celebrating the Land Rover, or both at once. Which, of course, it was.

The Ad That Ran Out of Room

Gossage didn’t make the Land Rover upmarket. He didn’t touch the car. He left it loud, rough, and exactly as it was.

What he did was find the upmarket people who were bored of quiet. A category of wealthy buyer that, in a sense, didn’t exist until an ad said he did. The adventurer. The man who buys rough on purpose. The ones who flew their own planes. Who wanted adventure and loved the idea of mud on the tires. Whether they actually used the Land Rover for off-road use was not the point. To them, the roar of the engine represented something primal. Something missing in their haughty safe lifestyle.

Every luxury market, it turns out, eventually grows a rebel. Fashion had Chanel and Dior; it also got Vivienne Westwood, who walked off the King’s Road in ripped clothes and ended up dressing people who hated the other two. Watches had Cartier, who, after making a wristwatch for the pilot Dumont, made wearing wrist watches for men acceptable; Patek Philippe and Vacheron Constantin; they eventually got Richard Mille, who strapped a Formula 1 engine to the wrist and started charging six figures for the privilege of ignoring three centuries of Swiss tradition

In 1965 the mid-market auto industry had a rebel, the Volkswagen. But the luxury car market had no rebel at all. Gossage saw the empty chair. And he sat a muddy, loud, square, magnificent Land Rover in it.

He didn’t move the car into the upmarket world. He built a new room inside it.

Which, as his next two Rover ads demonstrate, left little room for the product itself.

His ad for the Rover Grand Sport Version was so packed with enthusiastic copy, listing the armies (twenty-six), police forces (thirty-seven), archaeologists, titled persons, dog trainers, rock hounds, and racing drivers who used the car, that there was no room left for a photograph of the product. The footnote: “We meant to leave more room for a picture — but our enthusiasm got the better of us. So if you’d like a profusely illustrated pamphlet, please send us a postcard.”

And the ad that came after that one (one of my favorite ads of all time) not only didn’t show the car, but failed to mention Rover at all.

The one Gossage himself described as having callously flouted all the rules — worse still, he said, defying the brand name.

It mentioned neither the brand nor the product.

The entire ad was a dare. A provocation dressed as an invitation. Built on the premise that any reader who had been following the campaign would already know what “it” was, and any reader who hadn’t would be so intrigued by the confidence of the omission that they’d fill in the coupon.

I love this ad because it represents the purest form of something the entire content marketing industry has spent sixty years trying to articulate:

If your audience is engaged enough, you can stop selling entirely and let curiosity do the work.

The ad, in case you are wondering, was the Rover 2000 sedan. But you would only learn that by asking.

And speaking of asking...

The Nobel Laureate in the Mud

Gossage also created the first experiment in what we would now call influencer marketing, though considerably more literate than the kind involving protein shakes and discount codes, by giving the Nobel Prize winner and author John Steinbeck, the author of The Grapes of Wrath, a Land Rover.

The hope was not to get a testimonial or endorsement deal.

The idea was to let one of the most celebrated, land-rugged living American novelists talk about a car in his own voice, on his own terms, with his own sensibility.

And write about it he did

So much so that point one of the Rolls-Royce parody opened with a Steinbeck quote: “Except for rattles, I am against silence in a car,” writes John Steinbeck, a Land-Rover enthusiast, “and I don’t know a driver who doesn’t want to hear his engine.”

Steinbeck’s voice carried the kind of authority that no amount of advertising copy could manufacture. When a Nobel laureate says he prefers rattles to silence, the reader does not think: this is an endorsement. The reader thinks: this is an interesting man who has made an interesting choice. And the Land Rover becomes, by association, an interesting car for interesting people.

Gossage also enlisted Ashley Montagu, the British-American anthropologist (best known for his work on The Elephant Man), who contributed handwritten copy. And Ken Purdy continued his motoring observations across multiple installments, his byline carrying editorial weight that a client testimonial could never match. The campaign was becoming a collaborative literary project, a running conversation between a car company, a firehouse full of eccentrics, and some of the most interesting minds in America.

The Safety Pivot

When Ralph Nader published Unsafe at Any Speed in 1965 — the exposé arguing that most American cars were dangerously designed — Gossage and his agency pivoted. Rover, built for terrain where surviving mattered more than comfort, had always prioritized engineering robustness. The campaign reframed itself around the proposition that making driving safe as well as satisfying was the entire idea behind Rover.

The safety ads were likely shaped by Gossage’s partner Jerry Mander — a man who held the rather wonderful position of being conscientiously opposed to gas-guzzling automobiles while working at an agency that sold them. Mander did something more radical than write the copy: he put his own family in the ads. His wife. His children. And even himself.

The Show Closes

Gossage died in 1969, at fifty-two. He left behind a body of work so small it fits in a single book (The Book of Gossage, if you’re curious) and a reputation so large that people who have never read an ad of his somehow know his name.

He and Ogilvy disagreed about nearly everything. Ogilvy was suspicious of humor; Gossage was fuelled by it. Ogilvy believed in research and discipline; Gossage believed in conversation and instinct. Ogilvy’s ads were beautiful and authoritative. Gossage’s were funny and subversive.

And yet they admired each other enormously. Perhaps because each recognized in each other something that most of the people working in the advertising industry lacked:

A personal brand.

Gossage once said: “Nobody reads ads. People read what interests them. Sometimes it’s an ad.”

I have been brooding about that sentence for a long time. It seems to me to be the most important thing anyone has ever said about this business.

The Show Must Go On

What follows is personal branding advice for everyone, but best suited to creative people.

The most counterintuitive lesson first. As I mentioned before, Gossage didn’t make the Land Rover upmarket. He didn’t touch the car. He left it loud, rough, and exactly as it was. What he did was find the wealthy people who were bored of being wealthy. The ones who flew their own planes. Who wanted mud on the tires, not a clock on the dashboard. To them, the roar wasn’t a defect. It was the whole point.

I then pointed out how every luxury market eventually grows a rebel. I talked about Chanel and Dior, and Vivienne Westwood’s punk off the King’s Road, dressing the people who hated the other two.

Stop trying to make yourself fit the affluent world. Build the room in the affluent world that only you can fill.

Wealthy people don’t always like doing business with their own. Especially when it comes to certain types of services. That doesn’t mean they are expecting you to play some kind of subservient role. Quite the opposite. They may be looking for you to help them feel alive again. This is especially true of personal brands that work in the creative space, such as copywriters and designers.

Start with what you actually believe. This is easier said than done, and why it is sooooo important to build a personal brand that attracts the kind of people you want to work with and who want to work with you. Gossage’s first ad for Rover was about billboards, not cars. It cost him industry goodwill, but it earned Rover something far more valuable: the immediate trust of every reader who shared his conviction. But he was able to do that because he convinced them too. It was actually their idea, based on an article he had written a few years earlier. The executives at Rover were looking for a Howard Gossage. Not the other way around.

Make it a serial. Gossage split ads across editions. He referenced his own controversies inside subsequent copy. He teased future installments by name. He built narrative arcs across the campaign so that each piece enriched the ones that came before. Your posts are not isolated events. He also appeared in his own ads. They are chapters. You need to start treating your posts in the same way. Instead of posting about separate things, to them together, refer to them, make them all part of your story.

Steal the frame. Tell the opposite truth. Gossage borrowed the most prestigious ad format in existence and used it to celebrate everything the Rolls-Royce was not. You can do the same thing with any dominant format created by any dominant figure in your space: take the convention everyone follows to sell your service one way, replicate it with perfect fidelity, and then subvert the content. The collision between the familiar form and the unexpected substance creates a shock of recognition that no original format could achieve.

Be outrageous enough that they can’t look away. Gossage celebrated a Train Robbery in a car ad. He addressed violent career criminals as satisfied customers. He included maps of the crime scene. Yes, it was, in a weird way, kind of on brand for Rover. But the more important insight is that premium audiences have a particular weakness for audacity. They encounter caution all day long, from their lawyers, their advisors, their wealth managers, their endless parade of polished professionals who are terrified of saying the wrong thing. So while they may not let you do the same thing for them, the person who takes a genuine risk stands out to them with almost unfair clarity.

Play with the format like a musician plays with tempo. Gossage omitted the product photo from a car ad and apologized for his enthusiasm. He ran a fashion shoot for a vehicle built for mud. He mocked headline conventions inside the headlines themselves. The format of any medium, even LinkedIn, is a canvas, not a cage. Write a post that’s all questions. Start one at the end. Deliberately leave out the thing everyone expects. The person who plays with the medium signals to a premium audience that they are dealing with someone who thinks for themselves, and that signal is worth more than any amount of polished positioning. I have a formula for this. 70/20/10. Your content should be 70% what’s working, 20% repetition of what’s working, and 10% pure experimentation.

If you need help coming up with that 10%, you are really going to enjoy my free masterclass on June 16th, titled “How to never run out of ideas.” Click here to grab a seat.

Let other voices elevate you. Gossage gave Steinbeck a car and let the Nobel laureate write about it in his own words. He enlisted an anthropologist and a motoring journalist as collaborators, not endorsers. A message from someone your audience admires, in their own voice, is infinitely more persuasive than a message from you. By sharing the stage, Gossage made the stage larger. The selfless act was also the most effective one.

Create the invisible coupon. Wealthy people have an exquisite sensitivity to being sold to. What they cannot resist is genuine quality presented with the quiet confidence of someone who doesn’t need to announce it. You don’t always need to be so forward with everything. Especially with intelligent, wealthy people. The “If you want one” ad never mentioned the brand. It described an unnamed vehicle in sixteen tantalizing points and dared the reader to write in and ask what it was. The absence of the name made the car more desirable, because mystery is more seductive than declaration. Instead of writing a spammy call to action, every piece of content you create should have an invisible coupon at the bottom, something that makes the reader arrive, independently, at the conclusion: I need to know more about this person, or I need to tell them why they are wrong, etc. In other words, the call to action for every post should be the post itself because a conclusion, reached on their own, is worth infinitely more than any conclusion you could have spoon-fed them.

If you want to learn other ways to edit your copy to make it sound more human and relatable, then join 200 other writers and get in early on my upcoming Copy Hunter: How to Write Like A Human in the Age of AI course. Click here to learn more and use the code PRESALE to get it for $75 instead of 200.

And finally: have fun, or don’t bother. Gossage had fun. Genuine, visible, infectious fun. The fun was not decoration. The fun was the strategy. The thing that separates personal brands that attract genuinely wealthy, interesting, sophisticated audiences from those that attract other personal brand builders is this: the former are enjoying themselves. Wealthy people have the luxury of choice. The one thing they consistently choose — across restaurants, travel, art, advisors, everything- is the thing that feels alive. The thing where somebody is clearly having a good time.

And, like the Land Rover, not once did he change who he was.

Gossage had a good time. From a firehouse in San Francisco, with a tiny budget, a loud car, and the magnificent, soul-preserving conviction that the audience deserves a good show.

The audience got one. They came back. His clients got one too, and they kept coming back too. The audience filled in the coupons and bought the cars. His clients hired him and paid for the ads.

And not once, not in the billboard ad, not in the crime report, not in the Rolls-Royce parody, not in the sixteen-point mystery, nor in the way he talked about or sold advertising to his clients did Gossage pretend to be something he wasn’t.

He was a reprobate in a firehouse. Which is why the premium brands beat a path to his Firehouse door. And American beat a path to theirs.

Which, incidentally, exactly what my Art of Personal Publicity course is all about. Use the code ADVERTIISNGHISTORY to get 35% off.

See ya next week!

And if you have any questions about advertising history, let me know. Maybe I’ll cover it.

Justin Oberman

Last February, a literary agent asked me if I was interested in writing a book.

I said I was.

He asked, what about.

I responded, “You tell me.”

He then asked me to write an email to myself explaining what kind of books I would like to write.

So I wrote one. It was twelve hundred words, with comparison titles and chapter outlines.

He said it looked great.

And that’s the problem.

It was great.

If you had put it in front of eleven people in a conference room, they would have approved it, and two of them would have used the word “rigorous.”

And I know it was great because making those kinds of documents is, more or less, what I did for a living as the lead creative or head freelance creative for new business when I worked at ad agencies.

At some point in my career, I stopped writing advertisements and spent most of my time writing positioning documents, brand architectures, messaging houses, and making diagrams like that tall, skinny pyramid with the purpose at the top that nobody can read from the back of the room.

So when, during the pandemic, I was finally forced to build my own company and my own brand, I did what I knew how to do.

And that’s when I realized that brands are important, but the whole branding industrial complex is Bullshit.

The Forged Permission Slip

For ad agencies in the 60s, 70s, 80s, and 90s, a strategy document was a plan. And not just a plan. A plan of action. This is how we plan on growing your brand. This is the message. This is the media buy, etc.

Sometime after 2010, the strategy stopped being a document or a map and became the actual product.

A product in which a brand gets scoped and built. The key elements are visual identity and messaging. If ads are shown, they are shown in order to make the message and brand identity clear.

This brand's product is then presented on a Thursday (I have no idea why, but it’s usually a Thursday) to seven people, four of whom are usually looking at their phones and have the time. It then gets a round of revisions, mostly to change adjectives or adverbs in a mission or vision statement, or the color of a shirt a woman is wearing in a mock billboard ad that will never run because the brand can’t afford billboards. At some point, it gets approved. A brand book is created, or maybe not. Whatever the final deliverables are, they are sent, and the whole thing is placed on a server, where it will sit, undisturbed, for the natural life of the brand.

Sounds great, until you consider what that brand was graded on.

It wasn’t graded on any actual ads, products, or services in the wild.

Oh, sure….

People were questioned. Perhaps you ran a qual/quam research study or focus group. But even people who create ad campaigns will be the first to tell you how unhelpful those can be in terms of predicting anything.

No…

That brand was graded on nothing more than whether it survived the meeting.

And now the brand is excited to start its ad campaign using the new assets.

On paid Facebook.

Or social media.

The two places where your definition of what your brand is matters the least.

Or, even worse…

Real money is spent on TV commercials or outdoor ads, and six weeks later, the thing hits the real world, only to be rejected by it.

And so everybody starts talking about pivoting.

I know because I’ve been in the pivot meeting maybe fifty times. And the inclination to pivot is almost always right, because the pivot is based on a reaction to the real world.

Not a meeting.

Which is where it finally landed on me, about a year into working for myself.

To Safe to Fail

Everything real you could build has a way of telling you yes or no.

Ship a product, and people either buy it or they don’t.

Send a newsletter, and people either leave comments or they don’t.

Go on a date, and she either likes you or she doesn’t.

Run TV commercials, and people either start buying your product when they see it on the shelves, or they don’t.

Call yourself a copywriter, hedge fund manager, or accountant, and people will either hire you or not.

Just thinking deeply about these things cannot do any of that for you.

Neither can a strategy document

Thinking, planning, and strategy documents can only be improved.

And tweaked.

And tweaked again.

And I get why.

Planning and strategizing are soothing and, in a way, less risky. So, of course, you’ll spend eleven days on it. Or pay 100k for a company to build your brand in a bubble because you have found the one activity in the entire industry of marketing that is incapable of hurting your feelings, your nervous system, or proving you wrong.

And the better you are at strategizing, the worse it gets because if you can’t write a persuasive strategy, you get bored in an afternoon and then just start doing things. But if you can write one, you can stay in there for a year and call it work. And there are whole branding and strategy and consultants and coaches out there who will agree with you and gladly take your money.

That’s what happened to me.

My competence was the trap.

And since I was my own product, it went past wasteful into a crippling I did not expect because once I “finished” that beautiful document, I now had something to be wrong about.

Why the Finding Yourself Racket Works on Smart People

Because smart people are really into themselves so asking them to go deeper is like asking a kid if they want to go into a candy store.

Just kidding.

None of this is your or my fault, by the way. We were primed for it.

In his book The Fall of Public Man, sociologist Richard Sennett discusses 18th-century London café culture and how it was understood that when you went out in public, you put on a mask. And when you came home, you took it off. In other words, people’s personalities developed through their public actions, not private contemplation. You didn’t sit at home trying to “find yourself.”

People didn’t have any qualms about it either. There was no depression or neurosis about not knowing who you were. The performance aspect of this was not seen as something superficial. It was seen as a place for growth, a kind of laboratory for developing who you were to become.

According to Sennett, all of this changed with the invention of psychoanalysis.

Almost overnight, people shifted their attention from growing socially to growing alone. Now, instead of discovering who we are based on relationships with strangers, we’ve become a culture of narcissists obsessed with discovering “who we are” first. It convinced us that performance was somehow unhealthy, that there is really only one self, and that before you go out and use it in the world, you better make damn sure you know who you are and how to use it. And to do that, you need to sit still, look inward, and excavate your authentic core. And then act from your authentic self.

The result of this, according to Sennett, ironically led to a more confused and isolated society, with people unable to articulate themselves to one another because it made it a lot harder, if not impossible, for us to give ourselves the permission we need to become who we really are.

Whether you are branding a product or trying to discover who you are, the world today tells you the same thing. Find yourself first and then act. And with that came a whole industrial complex of therapists, coaches, and branding agencies willing to sell you the inside of your own head for a price.

But when you look back at great people and great brands, you see the opposite.

Three brands that were pivots first

I’m going to talk about this through branding and advertising because it’s easier for me.

Avis was number two behind Hertz and was losing money. DDB wrote them an ad campaign to move cars that quarter: We’re number two. We try harder. And it worked, so Avid kept it, and it became their brand identity for almost 40 years.

That’s how brands are built.

Even the brand that every branding agency likes to study and copy was built the same way.

As a matter of fact, Steve Jobs hated the word branding. He thought it was artificial and that the only thing that mattered was how a person felt about the thing in their hands. The proof of this is how he named his company Apple. He just came back from an apple orchard and was told the company needed a name so that it could open a bank account to receive investments.

He chose “Apple” because he liked that it had nothing to do with computers, and because it put his company in front of Atari in the White Pages.

Even Nike’s famous brand identity was formed the same way.

The first time Phil Knight saw the swoosh, he paid a design student seventy-five dollars for it, he said, and I’m quoting: “I don’t like it, but it will grow on me.”

And it grew on him not because of any studies. It grew on him because he understood that the important thing was not the mark itself, but getting started, putting it on some shoes, and starting to run (pun intended). It could always change later if it had to.

“Just Do It” came later. Again. As an ad campaign. But it is also the philosophy of how anything great becomes great.

I know that I am talking about branding and advertising here, but I think it is easy to see how this also applies to anything you do. And yes, when it comes to building your personal brand. But also for pretty much anything you are trying to build or improve in your life.

The right way to strategize is the wrong way

Now, before all you branding agencies, strategists, planners, therapists, or coaches jump down my throat, I want to point out that I am not trying to tell people not to strategize.

I still write positioning for clients, and they still pay me properly for it, and it’s still worth the money. I also have a 1:1 one-session where I have helped over 450 people discover who they are, who they should be serving right now, and what they should be writing and posting about.

The only difference between how most people approach strategy and how I do it is that I move it where it falls on the calendar. And by that I mean that the strategy always comes last.

This can happen in two ways.

The first way is mostly for people who are trying to figure out who they are, what they should be selling, or to whom they should be selling. And to do that, one of the first things I have to do is help people realize that there is an order to things. And perhaps what they are trying to be right now is not who they should be. And that even if someone is pivoting, they shouldn’t pivot too much, and that the best move is to help people solve the problem you just solved for yourself. I then spend a lot of time figuring out what that is, because most people are unaware of it, precisely because they have solved it.

The second way doesn’t need my help at all. Except when it comes to pushing and motivation, and it looks like this:

Your brand is a stain. You leave it by moving around.

One. Assume the thing already exists and start using it.

I am not talking about manifesting anything. I am simply talking about scheduling. If you want to be a copywriter, start calling yourself one and step outside.

If you want to start writing a newsletter, send one out under your name and the default font.

The gap between wanting to be something and becoming it is never just about talent. It’s about becoming it and then beginning to use it.

Two. Put on the public self and stop apologizing for the coat.

You already perform. You do not behave in public the way you behave alone, and thank G-d, because if everyone did, none of us would have friends and half of us would have no neighbors. So stop with all the psychoanalyzing and give yourself permission to perform so that you can learn how to make the performance better in public with input from real people.

The only way to build anything is to start using it.

Three. Start Doing Cool Things

Ben Franklin said, “You can either write things worth reading or do things worth writing about.” Most people obsess over the first half. But think about Ben himself. If he famous for some of the things he wrote and said. Sure. Is that why people still talk about him today? No. Ben Franklin also did things. Great things. Things people are still writing about.

And when you think about it, shouldn’t that be the ultimate goal of anything? To have people talking about you and wanting to be around you or follow you because of the things you do, not just because of the things you say?

This doesn’t mean you have to be like Warren Buffett. He is all over social media but doesn’t have his own account. You can do both. But where your emphasis should go is pretty clear.

Four. Write your strategy document as you live it.

Weeks one through four: act and observe. If ideas occur to you for a mission statement or core value or whatever, write them down for sure, but don’t get caught up in them yet. Do a hundred things, a dozen of them badly, then back up and look at the pile and notice eighty of them lean the same direction. Weeks five through eight, notice what’s landing and pour gas on it. Weeks nine through twelve are when you can finally start putting a strategy together.

And the best part is that instead of weeks or months, it takes about twenty minutes at that point, because you’re transcribing instead of inventing. And it’s also actually worth more because it’s describing a person or brand or whatever that really exists.

You don’t decide what you stand for

Now, one quick warning before you step outside with your public self on:

If you’re deploying somebody else’s capital or you’re scheduled to take out a man’s kidney Thursday morning, plan. Please plan. Plan hard, check which side, and ignore everything above.

As for everybody else, if you gave yourself permission to have a public self, took it outside, wrote down what you found, and are still having problems, then I’d like to see what you wrote and see whether what you wrote or decided was based on something real or just another forged permission slip.

I am really good at spotting the difference. I’ve spent twenty years manufacturing these, which means I’m really good at spotting the difference. So sign up for a 1:1 and let’s take a look. Every single person who has taken the time to speak with me has come out of it with a direction that, at the very least, works better than what you are working with now.

Or, if you think you can still do it yourself but just need more guidance, you can get all that inside my “Mastering the Art of Personal Publicity” course, where you will learn the deeper secrets of public self-discovery plus a much more powerful way to start using it to make yourself more known wherever it is you need to be more known.

Well.

Why are you still reading?

What are you waiting for?

Exactly one thing stands between you and the version of yourself you keep describing in documents.

And it’s time to start getting over yourself.

— Justin
Follow me on LinkedIn
View my courses

Watch me use this type of thinking on LinkedIn gurus in my LinkedIn newsletter: The Anti-Guru

I used Eden to help me collect my thoughts on this post and write the subject line for this newsletter.

If you already have an audience of eleven people who agree with everything you say, and you’d like to keep it that way, skip this one.

You’ve solved your problem.

This is for people who still can’t get strangers to care about the one idea they can’t shut up about.

The Problem

Every content guru tells you the same things:

Niche down.

Pick your customer avatar whose name is Brad, 34, SaaS founder, drives a Tacoma, lies awake about churn.

Speak to Brad.

Only Brad.

Always only Brad.

So Niche-Down Norman sits down and writes his 400th post about reducing churn.

And it’s a good post because Norman has become the single most qualified man alive on the subject of Brad.

But Norman is also bored out of his skull, and so, it turns out, is Brad.

The problem with the avatar rule is that it’s fine for some things, but it’s also wrong for others. For example, it may work well on LinkedIn, but not on YouTube or Substack.

On those platforms, you need to go the other direction.

Broaden the Packaging and Keep the Guts Weird

Take me for example.

My actual obsession is philosophy. Nietzsche. Wittgenstein. McLuhan. Semiotics.

I think the issues those philosophers talk about are fascinating. None of them, however, makes the best content strategy. Writing about Wittgenstein’s Tractatus is not how to get rich, and a post about Nietzsche’s Eternal Recurrence is not exactly stopping a lot of thumbs. So most people don’t write about the deep interests that interest them

But I really wanted to write about Wittgenstein and Language games one day. I realized that I already had a newsletter doing crazy numbers under the title “How to Improve Your Pricing With Showmanship,” So I took the shape that worked and poured Wittgenstein’s philosophy into it. New title: “How to Improve Your AI Writing With Language Games.”

Open it up and the first line informs you that most of what you think you know about language is pointless. Then I’m off into talking about Wittgenstein’s philosophy and theory of language games, Beatles in boxes, and theoretical talking lions. I annoyed a decent number of AI gurus with that post. But I also attracted more than I lost.

500k views between LinkedIn and Substack.

Those half a million people clicked expecting the usual productivity slop. But what they got was a deconstruction of metaphysical argumentation delivered by a guy who genuinely loves it. Which is a completely different but also pleasant experience from the one they signed up for, and that’s the entire point.

The smuggler’s headline

The best way to think about a headline is as a ship.

And the best way to think about what you want to write about is as the contraband on that ship.

The ship has to look like every other ship in the harbor, or it doesn’t get waved through. But the rarer the cargo, the more valuable it is and the more important it becomes to make the trip.

Your job as a content creator is to find the ship that can get your cargo to the most people. Which means finding the intersection between a validated title and your favorite idea so you can talk about whatever you want and get it in front of as many people as possible.

And to do that, you need to get people’s attention. Not because attention is the goal, but because it is the precondition for anything else you want to do to that person’s mind.

And validated titles can buy you that attention.

But only your obsession, the information you collect from non-viral sources, is how they remember you

Both halves are copywriting.

The ship is a promise.

The cargo is whether you can keep it by keeping them reading.

Most people are so bad at the first that they never find out whether their cargo is bad.

Some people only figure out the cargo is rotten after they solve their ship problem.

That’s the reason I built Copy Hunter: 52 hunts you, not AI, run your draft through to make it 99% better than even the best copywriters out there, with the added benefit of also making it sound more human.

So if the thing standing between your obsession and an audience is that you can’t write in a way that keeps people reading, you need to fix that first. Not all the hunts have been released yet. But you can get started with the first 20. Use the CODE PRESALE for a steep 24-hour discount [Link]

But this post is not about the cargo. It’s about the ship.

Skip the work of finding the best ship and your best thinking dies at sea.

What comes first?

Most people write headlines like this:

1. Write the thing you’d write if the numbers didn’t exist.

2. Figure out a headline from what you wrote or…

3. Look at other headlines people wrote for what you wrote.

That is the right order, but it is not the right thing to look for.

Instead of finding headlines that work for the topic you are writing about, if you want a lot of people to read what you wrote, you need to look for validated topics that you can tie into whatever it is that you wrote about.

So the new sequence looks like this:

1. Write the thing you’d write if the numbers didn’t exist.

2. Go find the validated topic that can be used to carry it.

3. Load one into the other and see who shows up.

So the free half of this newsletter ends with you holding one obsession and one problem and the homework of finding validated topics you can use to get people to read it.

What “validated” actually means, and why your instincts are lying to you

Most people hear “validated topic” and go grab a headline they saw once that felt like it did well.

That’s not a validated topic.

A validated topic is one that beat its own creator’s baseline. A post or newsletter or YouTube video that did 8x what that creator normally does.

I like to call those outliers.

But outliers are very difficult to find manually. Sure, you can open a creator’s profile and scroll. You can eyeball engagement counts or try to hold their average in your head while you scan and save links to a Google Doc. But that gets tiring fast. It’s almost a full-time job. A normal person gives up. Or worse, they just start marking the posts they personally like, which is precisely the bias you need to eliminate. What you like is the Cargo. Not the ship.

So most normal people give up.

That’s why there are so few people who are successful with online content.

Well, those days are gone.

The part where this gets easy

Eden is a platform that, among many other things, indexes creators and curated lists, keeps performance history, and can tell you which of their posts broke away from their own median. You can also use it to save all the social media posts that inspire you (for your cargo content part). You can also schedule and post all your social media posts from it. Besides Claude, Eden is slowly becoming my go-to second AI tool. It also connects to Claude, which is where it stops being a research tool and starts being a machine, because from Claude I can use and combine all of Eden’s features more quickly than I can from inside it.

For example: I have been using a Claude Skill to help me find validated outlier topics to attach my crazy ideas to.

Here’s the setup:

1. Sign up for Eden (Link)

2. Connect Eden to Claude as a connector (instructions).

3. Install my Claude Outlier Headline Script…

Read more

Not all.

But most.

And if you want to know who they are, pay attention to what they write about.

They are often the loudest about how AI will never replace human creativity, which is exactly the kind of whimper a man makes right before he gets replaced.

The stealthier ones did something different, however. They changed their job title. Which makes them much harder to find. But looking for signs of that changed job title is a good place to start.

I know that that's one hell of a way to open a newsletter.

But if you give me twenty minutes of your time, I will not only show you the receipts (because I used to be one of them), but I will also explain why I think there is still hope for you to be whatever it was you were before Pre-A.I. As a matter of fact, I will show you why, if you were good at it, there has never been a better time.

My Own Receipts

Sometime in the last two years, I stopped calling myself a copywriter, and I would like very much to tell you it was a strategic decision.

But that would be a lie because it was really fear.

When it became apparent that the machines could now produce serviceable sentences, the copywriters and ghostwriters of the world did not, on the whole, lose their jobs.

But they did lose their nerve.

And the first thing a frightened professional does, before he retrains, or retools, or does one single useful thing, is “reposition,” that is, he or she changes the name of what it is he or she does. I know this because I changed mine. It started innocent enough as becoming a ghostwriter, then a personal brand manager. Then I became, in my own mind, a publicist (but not a PR publicist, of course- an old-school Hollywood stunt-type publicist).

My reasoning was simple: A publicist gets people into rooms by getting people to do things, and a machine can’t walk into a room or do things.

Nobody made me do this. There was no client revolt, no invoice returned, no phone that stopped ringing. I did it in the privacy of my own skull, which is where all the really thorough cowardice gets done.

What Really Happened

What changed in 2023 is that a free tool started producing competent, structurally sound, entirely adequate copy in four seconds, which meant that suddenly every client on earth had a reference point for what adequate copy looks like.

But at the end of the day, that’s all that happened.

There was no copywriting AIpocalypse.

All that really happened was that somebody flipped a switch, and we all got a look at the room. And the room was full of people charging money for adequate copy. And for a lot of people, that adequate copy was good enough because even before AI, adequate copy sometimes was all someone needed.

Until it wasn’t.

So I was not afraid the machine would write better copy than me. Nobody who has read the machine’s copy closely is afraid of that. Great copywriters will always be great copywriters for reasons that I hope to discuss in the future. But for now, what I was afraid of was that the market would stop being able to tell the difference and that people would settle for adequate and that the clients that are already good writers would think it was the machine that did it, which is when put together a different fear altogether, and, when you think about it, a considerably more insulting one. Insulting not to the machine or myself but to the client. Because it assumes that people are fools. And the moment you privately conclude that your buyer is a fool, you will start doing foolish things, like go looking for a title they cannot price, because a title he cannot price is a title he cannot compare, and a title he cannot compare is a place to hide.

So I did the only thing frightened people ever do. I changed my name

OberThinking:: Fear renames. It never builds.

And I wasn’t the only one who did this.

I know copywriters who became conversion strategists. And I know conversion strategists who became brand architects. And I know the brand architects who became AI-enabled growth partners (which is four words doing the work of zero). Everybody started sprinting sideways. Or as a copywriter might put it, everybody started bolting on a modifier. Nobody, with very few exceptions, sat down and committed to going all in on who they already were.

I am not sure how that worked for other people.

But for me, it meant that most of my posts stopped working, and for roughly a year I published into total silence and diagnosed it as a hook problem, or a cadence problem, or a reach problem, or a the-platform-hates-me-personally problem. Which led to two years of frantic rebranding that did not improve my net income one penny.

Sorry.

I get properly heated about this one. Some of that heat is aimed at a guy I used to be.

So I think it’s important to point out that this did not mean I wasn’t making more money. But what it did mean is that I wasn’t making more money for the reason I thought I was. Which means, of course, that it was costing me money.

The Cobbler’s Kids

It took a workshop with the former AI-Guru Tasleem Ahmad Fateh (Taz) to wake me up. And not because he handed me a tactic. He did the opposite, actually. He kept asking what I actually do for the people who pay me. At first, every answer I gave was a noun invented to avoid the answer. And the word I was avoiding was the one on my first business card. I write things that make people buy things or pay attention to people. And, as any decent copywriter will tell you, there is no version of that sentence that improves by being made vaguer.

Every single person who has ever hired me, hired me to write.

Not for the publicity stuff or the strategy or the personal brand architecture or whatever I was calling it that quarter (though they would get that later, and for many that is why they stick with me). They came with a problem, I went away, and I wrote something, and that is the service. It has always been the service. The work never changed once.

Which explained the silence.

Because I think the algorithm knew. I think it knew exactly how that sounds. But whatever runs inside that thing could smell that I was talking about everything except the one thing I do, and more to the point, so could the people.

OberThinking: The algorithm isn’t measuring your hook. It’s measuring your honesty.

A man who believes his copy makes money does not need a new noun.

He needs better clients.

So I Am a Copywriter Again

I’m not a millionaire.

I’ve never sold you a laptop on a beach, and I’m not going to start. My primary business right now involves ghostwriting for high-net-worth clients. And I still limit myself to one traditional copywriting project at a time, because I’m not built to run six and I’d rather admit that than fake a bigger operation.

So here’s the ridiculous thing I’m announcing. I do not plan to just become a copywriter again. I intend to make an even more embarrassing claim than that:

I intend to become the first copywriting guru of the post-AI era.

I know how that sounds. But I have decided I would rather say it out loud and be measured against it than say something smaller and be safe, and if that irritates a few people, that is fine with me.

There's a hole in this market the size of a house. Every copywriter in the space is still teaching a pre-AI game of tips and tricks, which do not go away, but need to be repagaged. So here is how I am repagaging copywriting.

Copy Hunter. Copy Hunting is the pre-writing and post-writing system I use to make sure people read every word I write. I originally created it before AI. I then abandoned it after AI. But I am now bringing it back for reasons I have already discussed above. Objectively, it is a course about hunting. What to hunt for before you write and what to hunt for in what has already been written. The Copy Hunting part is the latter. And it consists of 52 Hunts that will, if you follow the direction, take anything you (or AI) writes and make it better than something even the best copywriters will write. It is not, however, a course about prompts because prompts are the cheapest part of this trade now, which is precisely why the best copywriters have become expensive. [LINK]

A Sprint Toward Premium Clients with Tasleem, for copywriters and ghostwriters, on how to market yourself in the post-AI era, specifically, how to go after high-net-worth individuals and outrageously profitable businesses and nobody else. The problem with most copywriters is not their copy. It is their address book. I spent years working out how to get in front of people who do not flinch at a number, and I used it on my own behalf, and it worked, and it is teachable. There is no Link for this yet. But if you reply to this email and tell me you are interested, I will personally make sure you are one of the first to know when it is.

The Daily Copy Hunter: A New Daily Newsletter about Copywriting. Why Daily? Because that’s what copywriters do. And because it helps keep my newsletter list honest. It will consist of nothing but craft, mechanics, tips, and the small ugly tricks that the best copywriters use to create very different results than average copy, but all packaged up to address the ten-ton AIlephant in the room. It is not fully up and running yet. But the list is open, and if you want it, get on it now while the archive is still short enough to read. [LINK to Subscribe]

*

Don’t worry. OberThinking is not going anywhere. It's just going upstairs. This newsletter will lean harder into the philosophical end of things: human nature, self-deception, the seamy side, why we buy what we buy, and why we lie about it afterward. It will also continue to offer people unique ways to use AI to think more creatively and solve life problems. Plus, it will serve as my own personal evidence because every issue of this thing is a demonstration that the advice in other places works: you subscribed to it, you opened it, and you have read this far into a newsletter with only one picture in it.

*

As for the work itself: I have started taking direct response again, and website copy, and there is a short branded film underway, with a brand campaign starting soon after. I am still holding it to one copywriting project at a time, because the bulk of my hours belong to ghostwriting for high-net-worth individuals, many of whom, it turns out, have been quietly tapping me for copy all along.

They never once asked whether I called myself a publicist.

The clients were never confused about what I do. Only I was.

More about what I mean by that next week.

In the meantime, it is good to be myself again, even if myself is out of style.

— Justin Oberman

The first one has a gift and no great affection for hard work.

The second one has no gift but will knock himself out trying.

Which do you hire?

The correct answer is you hire the first.

If you said the second, you are probably not going to enjoy his newsletter.

The Self Improvement Industrial Complex

The self-improvement industry is the most successful sustained advertising campaign in the history of the trade.

The fact that some of the best self-help books were written by former copywriters should be enough to make you remember that the self-help industry doesn’t sell a product. It sells a deficit.

Nobody buys the book honestly believing it will work. And you know this because you have bought eleven of them and you can name what changed after none of them. You buy it because for the price of a sandwich you get to spend an afternoon as the kind of person who is doing something about himself. And it is that feeling that is the merchandise. Not only that, it is cheap to manufacture, it evaporates in about four days, and it comes back reliably every January, which makes it the best crop in American commerce.

I’m embarrassed to admit this, but I’ve done this.

For years I sold people a feeling and called it a lesson.

Not a lie, exactly. The feeling was real. It just wore off in about four days.

Here is how the trick works

You write something that hands the reader the sensation of doing something about themselves. Not the doing. The sensation. And then you make absolutely sure the piece never solves the problem, because a cured customer is a dead account.

No industry has ever been asked to cure itself out of existence and cheerfully agreed to it. Not one. So the thing being sold was never improvement. It was the appetite for improvement, which is cheap to manufacture, evaporates fast, and comes back every January like a crop.

You have bought eleven of those books.

You can name what changed after none of them.

OberThinking: The self-help industry does not sell you a result. It sells you an appetite. A result ends the relationship. An appetite renews it.

The old me would take everything above and turn it into a lesson on how to write like a self-help author, and it would be a great newsletter, and it would work, because that stuff always works.

That is not the lesson that has been sitting on me lately.

The lesson sitting on me lately is the exact opposite one.

Because the same machinery that sells more of whatever you are selling is the machinery that has you failing at whatever you are failing at.

If you have a natural aptitude for something, you can accomplish a great deal by exercising it without working terribly hard. That being said, if you do work harder at it, you can accomplish more. If you work like mad, you may even make history. But if you are not especially gifted at the thing, you can labor at it like a monomaniac and produce only mediocrity, ending up, all pooped out with nothing much to show for it.

The entire self-improvement apparatus (and pretty much every piece of online content you read) exists to service the second person and, more importantly, to keep him or her from finding out. Because the moment they find out, the moment they accept that the thing he or she has grinded at for however long is a thing they are merely ordinary at, the revenue stops because their striving is the product. Not their progress. Their striving.

And it’s during times like this that we all ask ourselves the same question.

Is it the world, or is it me?

And in this newsletter I’m going to show you why it’s neither. And to show you why, I need to introduce you to a paralyzed Italian philosopher who published a book in 1961 about riding tigers.

Why You Don’t Care Anymore

The problem with every productivity system, morning routine, five-step plan is that it assumes the ground is stable and that if you organize yourself hard enough, the world will hold still and reward you. And you have tried. You alphabetized your life, but the numbness and the failure stayed. Then a long time comes another guru with another system, or an improved version of teh system, to tell you that the reason it failed is that you did something wrong.

The truth the self-help gurus don’t want to tell you is that you didn’t do anything wrong. Because all their tools, systems, and techniques are built for a solid world. But you and I aren’t standing in a solid world. The world today is very much a liquid one.

So the problem is not that you did something wrong, stopped caring, or feel like giving up. The problem is that you have been told your whole life that not caring or giving up is a malfunction. Or Burnout. Or anhedonia. Or a phase. Or something to medicate, or journal through, or optimize your way out of.

During times like these, the opposite is true.

As a matter of fact, during times like these, not caring may be the strongest strategy you have.

In 1961, a paralyzed philosopher named Julius Evola published a book called Ride the Tiger.

The book opens with a strange disclaimer:

This manual is not for everyone. It concerns a specific human type. The one who is involved in the modern world, works in it, moves through it, but does not inwardly belong to it. A person who feels like they answer to rules from somewhere else.

As you can already tell, Evola was a very unique and deeply compromised figure. He spent the 1930s orbiting Italian fascism, and I will be the first to say his politics deserve the rubble they are buried in. But buried inside this book is the sharpest answer anyone has written to the question eating at so many people in this Post-AI era where things move too fast, and it becomes impossible to keep up.

What do you do when you stop being able to care?

Evola’s answer begins with an old map.

Hindu cosmology divides time into four ages, descending like a staircase. Gold, silver, bronze, and then the basement. The basement is called the Kali Yuga. It is the dark age where every structure that once held religion, custom, hierarchy, the algorithm, even meaning itself, dissolves. The texts describing it are thousands of years old, and they read like your morning feed on LinkedIn where institutions are hollow, authentic bonds are optional, attention is scattered, and everything is for sale.

The basement is part of a sequence.

Meaning it is a scheduled season, not a surprise malfunction. Meaning what is happening around you is not a crisis waiting on your fix. It is a tide.

You do not take a mop to the ocean.

Now read your own history through that lens. Look at the numbness you have been treating as a malfunction. Take a closer look at your growing inability to care about the ladder, the feed, the game. When you realize that it is, for the most part, just a reaction to the basement, it stops looking like depression and starts looking like an immune response. Which means your system (or borrowed system) is not failing to engage with the world. It is just correctly detecting that much of what surrounds you is not worth engaging.

Which means you are not broken.

You are just unassigned.

But more importantly, it means that you were built for a structure that is not currently standing. The question now is what you can do about it

OBERTHINKING: Your numbness is not a malfunction. Your numbness is a reading.

Why You Can’t Just Quit, Though

Why you can’t just quit, though

People exist by the consent of other people.

I don’t mean that as a metaphor. Outside of a few hermits and outlaws, there is nobody alive whose existence doesn’t depend, daily and a little humiliatingly, on other people continuing to agree they should have one. Every handshake, every smile, every like is a small application for renewal.

So think about what that does to your self-improvement.

If your existence runs on consent, then your self-improvement was never a private project. It’s a consent-maintenance program. The 4am routine is a tithe. The endless upgrading of the self is rent, paid to stay visible to people whose approval you have never once examined and could not defend under oath.

When your self-improvement is built on the consensus about what self-improvement is, you are not trying to become better.

You are trying to remain permitted.

And I am not telling you to stop caring what people think. That advice is itself a genre, written for the independently wealthy and the genuinely deranged.

I’m telling you to find out which of your ambitions are yours and which ones you are renting.

Because once you know that, quitting changes shape entirely.

Burnout is detection sold as damage.

The morning routine is rent sold as discipline.

The system is obedience sold as freedom.

The next book is appetite sold as an answer.

And quitting, the real kind, the kind you were taught to fear like a disease, is the only honest audit most of us will ever run on our own lives.

In other words, quitting is not withdrawal from life.

Quitting is canceling a subscription you stopped reading years ago and kept paying for because the charge was small and the cancellation required a phone call.

OBERTHINKING: Quitting = reallocation (not withdrawal).

What Does It Truly Mean to Stop Caring

Several issues ago, I wrote three newsletters. The first one was about How to Want to Stop Being So Political. The Second was about How to Want to Be Less Creative. And the third one was “The Uses of Artificial Stupidity: How to Want to Be Less Good at AI.

The modus operandi behind writing them was thus:

Posts and newsletters to spur the under-ambitious are everywhere. Content to calm the habitually over-ambitious, and thereby make them more effective, is considerably less common.

Note what I am not saying.

I am not saying that ambition is a vice. All I am getting at is that perhaps one’s ambition is badly allocated. And that most of us who are trying, but failing, are pouring effort down nine chutes at once and arriving nowhere with any force, and that the most useful intervention in this case is not additional effort but the withdrawal of effort from the places it is being burned. And yes, what I am describing here is in many ways a set of techniques for breaking habits. But what makes my approach (and the approach of this newsletter) different is that the habits I am specifying are, for the most part, seen as good in the eyes of the world (and therefore also the self-help industry). Which, in a way, makes them even harder to break. But be broken they must.

So if you only get one thing out of this newsletter, let it be this: The art of giving up, put to use, means only this: you are bad at some things, no system will fix it, and the correct response is neither shame nor a better app. It is a reallocation of the energy you are frittering so you can start spending it where your gifts already sit. Everything else you can either do adequately or not do (or, better yet, hire someone to do) and stop performing for an audience that was never watching.

Which raises the harder question, the one the productivity clergy will not touch. If quitting is so obviously the correct answer, why can none of us do it?

How to Stop Caring

There are two kinds of not caring, and they look identical from the outside. But one is inherently more dangerous than the other.

The first kind is utter collapse. This is the kind of not caring that comes with a numbness of a person going under. This person needs help, not philosophy.

The other kind of not caring is detection, the flat reading of a person whose instruments work fine in a fallen age.

The difference between these two types of not-caring can only be found when something real happens. Something like, for example, AI. Because when something real happens, the collapsed person feels nothing then either. The detector, on the other hand, comes alive.

And when you stop treating your numbness as a wound and start treating it as evidence, three things shift.

First, the exhaustion lifts. Half your exhaustion is maintenance work propping up structures that serve nothing. These could be beliefs you inherited, ambitions you never chose, or even relationships running on inertia. A dissolving age like the Age of AI stress-tests everything. Whatever needs propping to survive was never yours. But whatever holds without you is what you need to hold on to. Because that is you. And being able to name the props reallocates the energy.

Second, you become uniquely equipped to act cleanly. The person who has stopped craving what this age sells can work without renting their pulse to the outcome. While your colleagues ride metrics like a mood swing, inflated by every win and by every loss. You, with nothing to grasp, can simply act by caring completely about the doing while caring nothing for the scoreboard.

Third, you stop being conscripted by the outrage machine. The feed that hands you a fresh emergency every four hours and charges your nervous system for the privilege only works when you participate. So when the pull arrives and finds nothing to grab, you get your evenings back. And your blood pressure. And your family’s dinner.

Ride the Tiger

The title of Evola’s book comes from a Far Eastern saying: when a tiger charges, you have three options. Fight it and be mauled. Run and be run down. Or the insane one: as it leaps, swing onto its back and ride it. Not to tame it, because you cannot tame a tiger. You ride it because on its back is the one place its claws cannot reach. As a matter of fact, when riding the tiger, you only control one thing: the seat. Where the tiger runs is the tiger’s business. Whether you are still on it when it stops, that is yours. And, if you keep your seat long enough, the tiger will exhaust itself. Then you can dismount alive, on your terms.

Now switch out the word tiger with AI, an algorithm change, a market change, or whatever else you feel is dissolving everything but you in the world right now.

Here are the four moves you need to make to ride those tigers. Do them in order this week.

1. The Audit. One page, two columns. Column one: everything currently holding your life up: job, relationship, beliefs, image, routines. Column two, for each entry, answer the following question: If I stopped actively propping this, performing it, defending it, forcing it, would it still stand? Do not act on anything. Just mark the props. What holds without you is load-bearing.

2. The Exposure. The numbness you have now or are beginning to feel is a flat, gray deadening tarmor that mutes everything because somewhere your system decided feeling was too risky or expensive. What you need to do now is loosen it with small, deliberate exposures to things you do not want to be exposed to. Maybe it’s the song that used to wreck you at nineteen played all the way through, volume up, without reaching for the phone. Maybe it’s the hard conversation entered without the exit already rehearsed. Maybe it’s grief, when it comes, taken straight without a chaser. Whatever they are, each one is a rep that loosens the armor. But not because you got tougher, but because you stopped outsourcing the holding to the numbness. If you feel yourself getting tougher, stop.

3. The Amputation. Pick one project you are building this week. Before each session, say it out loud: the work is mine, the result is not. Then watch for the moment mid-task when your mind leaves the work to check an imaginary vanity scoreboard like applause, or metrics, or the boss’s face. That flicker is the attachment firing. That’s O.K. Do not fight it. Just acknowledge it and return to the task. The skill is not preventing the flicker. It’s the habit of coming back and how fast you do.

4.The Unhook. Everyone has a topic that reliably hijacks them. For you it might be politics, a certain kind of news story, a specific grievance that lives in your feed. When that topic appears, something happens in your body: heat in the chest, the reply already composing itself. It’s important to realize that that pull is not you. It is the machine wearing your conscience as a costume. Most of the time for most things in life, there is no action you can actually take. The outrage or even the success is theater, and you are donating your evening, your blood pressure, and your family’s dinner time to a machine that will never know you existed.

So the next time that pull arrives, count to three.

One: name it aloud: that is the pull, not me.

Two: find where it lives in your body right now.

Three: ask whether there is any real action here that belongs to you. If yes, take it cleanly. If no, let it pass through. You just kept your seat.

A Note, Filed in the Ordinary Way

On Thursday, July 30th, at 8:30 in the morning Pacific, Tasleem Ahmad Fateh and I are teaching a free session on how to write like a human in the age of AI. Free means there is an ask at the end. There is always an ask at the end. I have just spent seventeen hundred words telling you not to be fooled about what an application is, so I will not open this one by fooling you.

But it is the same argument, not a change of subject.

Chances are, part of your feeling of numbness is the result of your feed filling with machine-made copy that is free and adequate. Adequate being the dangerous word. The machine produces, at no cost and infinite volume, the exact median of your trade. It has read everything inside your niche and nothing outside it, and it cannot drag anything back from outside the trade, because for the machine there is no outside. Which means the median is now free, and everything you publish at the median is competing against an opponent that never sleeps, never doubts, and does not need to be paid.

That is a tiger to ride.

And the free webinar is the tiger bending over to let you on.

Grab your seat on the Tiger here

Or do not. That is a live option, and I have just spent an essay defending it. But if you are going to keep filing applications, and you are, you may as well stop filing them in the same handwriting as everybody else’s machine.

Ran a command, read a file

Ran a command, read a file

This Is Not An Excuse for Doing Nothing

Riding the Tiger is not a permission slip for doing nothing. You have seen the man who read it that way. He is in every comment section. Fluent in decline, five years into building nothing and contemptuous of everyone still trying.

“The age is fallen”, he rightly proclaims.

“Nothing matters,” he mistakens. Because he still matters.

His rot is aristocratic, and none of it has anything to do with t riding anything. It is more like being dragged, with a philosophy degree. So the test never changes. The rider acts. Full intensity, zero grasping, seat held. If, for whatever reason, your detachment is making you feel smaller, or duller, or more contemptuous, it means you are not riding the tiger. And if you were, then you fell off the tiger a while ago.

Riding the Tiger feels like more life, not less.

That is how you know.

So back to the question you have been asking in the dark: Is it me, or is it the world?

And the answer , as you can see now, is that it is neither.

It is a dissolving age doing exactly what dissolving ages do. And your numbness to it is not proof that you are broken.

It is proof that you noticed.

So the next time you unlock your phone to check out whatever social media platform you check out regularly, there is a flat half-second before the feed loads. That is the tiger lowering itself for you to mount.

Happy riding.

— Justin Oberman

Dear Friends and Paid Subscribers,

Sit down and get comfortable, because this week Substack announced it’s using a detector called Pangram to catch AI writing, and Ruben went to war with it.

And people have opinions.

Here is mine.

But I also just want to say that even though I find them highly unreliable, out of all the AI detectors, Pangram is the one I use. As a browser extension, it saves me time by telling me if something was 100% written by AI.

But it’s also fine to edit your own content alongside it. As a guide. Not as the truth.

I’ve used almost all of them and do find it to be the most… helpful.

You can try free for 7 days by clicking here.

The Return of Ruben

Of course, it didn’t take long for AI Guru and human illusionist to weigh in with a very useful newsletter about how to avoid AI detection.

You can read it here:

But here is the TLDR:

Ruben spent three hours and $34 in credits trying to beat Pangram and couldn’t.

So he escalated the fight by building a custom Claude skill, a robot editor whose entire job is stripping the AI out of AI writing.

He had AI write a post on a very mundane subject (the origin of the name Ruben)

He then ran his draft through Pangram, and once again the Verdict was 100% AI-generated.

Then Ruben deleted a single em dash, typed a colon in its place, and scanned the copy again. This time the verdict flipped to 100% human.

Now Ruben’s conclusion from all this is that detectors are basically a coin flip and here’s how to slip past them. And he’s giving his skill away free, so his readers can slip past them too.

Which, when you think about it, is one of the safest things an AI-Guru can say. Especially when you run the newsletter itself through Panagram’s AI detector:

To be fair, my conclusion is the same as Ruben’s. AI Detectors are a coin flip.

But with one major diffrence.

And the diffrence is that my conclusion is worth money.

Ruben's $34 mistake

The biggest problem with any time Ruben talks about writing is that he seems to only think that what differentiates writing is a surface-level thing and that the connection between thinking and style or voice and style can be separated.

They can’t.

I downloaded Ruben’s skill and took it apart. All of it, including the test log he packed inside, which is super interesting because, when you read it, the data inside ends up demolishing and disproving his own newsletter.

Here’s what’s in there:

Exhibit one: The disguises don’t work

The newsletter tells you detectors are basically guessing because “I can change the style infinitely.” Prompt a new style, he says, and AI writing is no longer AI writing. (Which is true and false for more reasons than I can explain in this newsletter. But the main one is understanding what a “style” actually is, which I talked about at length last week. )

The appendix he zipped into that free download shows him throwing eleven styled rewrites at Pangram. Clipped and punchy. Long and rambling. Lowercase texting mess. Deliberate typos. Slang. Even one that mimicked the style of his own handwritten stuff, none of which, as I talked about at length here, are what language philosophers or real writers would refer to as styles. A writer’s style develops from their use of propositions, not from their use of grammar.

But Ruben calls them styles, and he has eleven of them which create eleven verdicts, again, that are100% A. His log’s own conclusion says it flat: style is not the lever. Which again is wrong. Because those things are not style. Those things are grammar. So it should really read... grammar is not a lever.

Which, incidentally, means that em-dash colon trick didn’t crack a safe. It stumbled onto a crack in the paint. A crack a future Pangram update can simply paint over. Which would put everyone who built a publishing strategy on a punctuation mark back in the flagged pile.

Exhibit two: The recipe that DOES pass requires writing worse

Ruben’s script instructions for rewriting, and I am reading from the man’s own skill now, are basically a prompt that says “write this worse.” The instructions say to keep it under 160 words. Delete most of the argument. No punchlines. No thesis. No structure. Make sure nothing lands. Basically, “take what I wrote and mutter it at the page like a man ranting at a bus stop.” His log here even records a rewrite that failed detection because it was well-written, and passed the moment he flattened it.

Which is great when it comes to fooling AI detectors. But sucks if you actually plan to use the copy.

The example that Ruben gave in his newsletter proves it. Sure, the AI version of the post about the origins of the name Ruben was very AI-ish. But the one that passed was not only boring as hell. It also promises to be written in the same boring style as everyone else's.

Which may or may not be OK if you are writing for pleasure or non-commercial purposes.

But if you are writing for marketing or sales or for any persuasive reason (other then giving a lecture about the origins of the name Ruben), Ruben’s solution is equally worse because the only automated rewrite that fools the robot is one that’s useless for anything having to do with marketing or sales, because a rant with no point has never closed a sale, won a client, or built an audience in the history of commerce.

In other words, the machine can only look human by becoming worthless.

Exhibit three: The reliable way through is a human draft.

What his tests inside his own script prove is that, at the end of the day, something written mostly in your own hand can still have a fistful of machine AI-like sentences (up to about forty percent) and pass the detection clean. But once you paraphrase the human sentences, or let the machine’s share creep past half, the verdict flips right back.

You see what his own data is saying?

Underneath all the software, the detector is hunting for exactly one thing: whose hand wrote this. It is not hunting for punctuation or vocabulary use.

Which means that after spending $34 in tokens to investigate and build a custom-built robot, the secret buried in his own fine print is this: the most reliable way to bypass an AI detector is to do the writing.

Every dead copywriter I ever learned from is nodding in his grave.

And now the part where I quit being fair to Ruben, because there’s a bigger error under all of it (which has to do with the findings of Exhibit 3.

The Detector Is Not Your Audience

Pangram has no wallet. Substack’s bot has never bought anything in its life. Which means you could win that “100% human” gold star every day for a year and not have one deposit deposited into your bank account because the detector that decides your career sits behind your reader’s eyes. And that detector runs a different test. And that test isn’t about whether or not a machine wrote this. It’s: did any thinking actually go into this at all at any level? And by thinking I unfortunately mean work. Specifically, thinking and editing.

And thinking and editing cannot be gamed with a colon. It can only be answered with specific things that happened to you and how that experience comes across in your writing.

Funny thing is, Ruben knows this in his bones. In that same newsletter, he tells the CEO of Substack, quote: “We must chase & kill AI slop the same way we chase & kill bots.”

Chase and kill. His exact words.

Ruben, that is called a hunt.

But the answer is not to hun AI Slop with AI.

It’s to let human beings decide for themselves what it likes and what it doesn’t. Adding a layer of the coin toss that is AI detection will influence that decision and not in positive ways.

If Substack’s AI ever detects AI in something I write, then I can prove I had no AI involvement; I am actually prepared to sue.

The solution is also to encourage people to hunt for AI slop in their own content. But once again, not with AI, but with their own brains.

It’s also why I developed the Copy Hunter Field Guide for Writing Like A Persuasive Human Being in the Age of AI. The Field teaches you 52 things to hunt to make anything written by AI or even yourself sound more human.

The part of the newsletter where I’m supposed to upsell you.

Instead, I’m going to talk about a free thing for regular subscribers and an awesome opportunity for paying ones.

For Free Subscribers

Join me and LinkedIn’s OG Guru Tasleem (Taz) as we discuss how to make sure your writing always sounds human during a FREE webinar on July 30th at 8:30 am PST. Grab a seat here

.

For paid subscribers…

Drop an AI-generated post or, better yet, your most recently failed post in the paid subscriber chat, and I’ll perform a free autopsy on the first 10. A genuine, rip-snorting, no-holds-barred edit where I will mark every AI tell, every flow-break, every buried “you,” every lack of research or ideas, and name which of the 52 hunts would have caught it. People pay real money for this. You’ll pay with a reply.

Why give it away?

Because I’m pretty sure that once you watch me go hunting in one of your dead or AI-generated posts, you’ll want the whole field guide. And because a free edit is the only honest résumé in this business, either the corpse sits up, or it doesn’t.

Fair warning, so you know who you’re dealing with: I’m a slightly used copywriter. I’ve written flops. (Ask me about the Makari ads sometime.) But I’ve also spent my whole career studying the masters, from Powers to the Halberts, and Copy Hunter is everything they knew plus the nine hunts they never needed.

If what I do doesn’t work, I don’t eat. So send me what you got and let me show you what I can do.

By the way, this newsletter was written the same way.

The various ideas and angles in it were discovered by Idea Hunting

The details come from Research Hunting.

The perspective came from Self Hunting

I then ran that information through an AI Claude Project I created that follows the various letter-writing styles I appreciate from copywriting legends like Bill Jayme, Gary Halbert, Eugene Schwartz, and Jim Rutz.

The resulting copy still came out 74% AI copy.

I then spent an hour running through the 52 Copy Hunts until it looked almost nothing like what the AI spit out.

I then ran it through Pangram again. Here are the results:

That being said, I do want to put something in writing:

Disclaimer

Using the Copy Hunter system alone is not enough to fool Pangram.

As a matter of fact, Ruben’s data shows that editing for quality is exactly what detectors read as machine-planned, and I don’t want to sell you his mistake with my name on it.

A lot still depends on the Idea Hunting and Research Hunting you do before that.

But provided you actually have something worth writing about, what the 52 hunts will do is harder and worth more:

Each one forces you to find details in your draft to kill and replace with something only you could have written. It is a step that, when done right (which requires more than just making your writing worse or removing an em-dash), no skill, prompt, or robot editor can perform, because the raw material is your life.

This works whether or not you use AI to write.

But if you use AI to write, then what I can promise you is this:

Once you start running the hunts draft after draft, two things will happen:

The first is that they will begin to become second nature.

The second is that your ratio between man and machinein your writing will begin to shift dramatically as the machine becomes the garnish and you become the meal. Your readers will also feel it immediately. And while there is no way to guarantee what a detector will do, the odds will turn incredibly in your favor because by the end of your hunting you will have actually written it.

Ruben’s readers will spend this week installing a free skill that he only spent $32 on and whose own test log says the disguise fails eleven times out of eleven but also makes your copy sound just as bad as everyone else's, not to mention useless for marketing purposes.

Or you could spend twenty minutes a day for the next year becoming impossible to fake.

What you get:

52 hunts / Videos (15 minutes each)

Five tiers.

A field checklist for beside the keyboard.

A workbook where you do the reps.

I am releasing the hunts slowly. So only 18 have been released.

When the course is finished, it will be $250

But you can get it now for only $52 if you use the code PRESALE

Here’s a link for more information.

Justin

P.S. Download Ruben's skill. I mean it. It's free, and the appendix is the best argument for Copy Hunter anyone's written this year, including me. You can download it here if you want to try it yourself: https://www.dropbox.com/t/fORTSF4grrSCzrMN (the password is RUBEN-HOWTOAI). Then come get the 52 hunts and do the part his robot can't.

P.P.S If you want to make it harder for people to detect if your content is written with AI using Substack's default detector, just make all your newsletters paid newsletters, add the paywall to the bottom of your email so teh whole thing is visible to everyone, and send the sample email before the paywall to all subscribers. For whatever reason, you cannot use the AI detection for newsletters you are not subscribed to, or for newsletters you need to pay for.

Read more

I want to be upfront about something.

I didn’t choose the subject of this newsletter.

The data did.

There’s a theory going around the creator world called the outlier method. It goes like this: don’t guess what to write about. Look at other people's posts that performed dramatically above your or their own baseline, not your most-liked posts in absolute terms. I’m talking about the ones that did 3x, 5x, 8x better than your median. Those are your outliers that the audience has already voted on. The topic is proven. Your only job is to talk about that topic from a new angle, in your own words, again and again.

So I ran the experiment on myself.

I analyzed 105 of my own LinkedIn posts against my baseline.

My median post performs at about 1.2x my average. My outliers ran between 4x and 8x. Now normally the first thing you learn when analyzing other people's outliers is that they are almost always about vague topics.

That was no different for me.

What was different for me, however, at least when it came to the posts over the last year, was that they were all about the same subject.

The post about the guy who sent me a 60-page AI-generated strategy doc he clearly hadn’t read himself got 7.3x my baseline.

The post about the 1,168-line rules file someone built to stop AI from sounding like AI, and how Claude itself refused to apply it. 6.5x.

The post about LinkedIn announcing it would fight AI slop... with more AI. 5.5x.

The handwritten note explaining why you can’t use AI to make your writing sound more human, because AI is not human. 4.3x.

Every single one of my outliers is about the same thing: why writing produced by AI sounds the way it sounds, and what it’s doing to the people who publish it.

So according to the theory, this newsletter should be about that.

So fine.

It is.

But first I want to take the theory itself apart, because it deserves better than the way it’s being used.

The outlier method is 100 years old

The outlier method isn’t new. It wasn’t invented. It was rediscovered in the same way the best ideas in marketing always get rediscovered every generation by whoever bothers to test things.

In 1923, Claude Hopkins published Scientific Advertising, and the entire book is one idea: stop arguing about which ad is best and let the results tell you. Direct-response advertisers ran coupons in newspapers and counted which headlines pulled. The ad that pulled got kept and became the control to be studied and rewritten. The ad that didn’t got killed, no matter how much the copywriter loved it.

An “outlier post” is just what a direct-response man in 1923 called “the ad that pulled.” And the analytics dashboard is the coupon. Nothing has changed except the speed of the count.

David Ogilvy built an agency on the same principle: research first, opinion second. And the reason it works hasn’t changed either: your audience is voting constantly. The problem is, and most of us ignore the ballots. And the sad part is why. Usually it’s because we’re bored with our own hits. We wrote about the thing, it worked, and now we want to write about something new, because we need novelty. But as the outliers of most content creators prove, audiences don’t need novelty. They need to know things like “how to never forget what they read,” or “never run out of ideas,” or “become the smartest person in the room.” The only novelty they want is a different opinion on how to accomplish those things from different people.

How to find your outliers

1. Find your outliers relative to your own baseline. Not your most-liked posts. A post with 90 likes is an outlier if your median is 20; a post with 400 likes is a dud if your median is 800. You’re looking for the posts where the audience’s response was disproportionate to your normal. That disproportion is information.

You can do this by hand with a spreadsheet, the way Hopkins would have. I don’t. I use Eden, which lets me pull up any creator (including myself) and filter their entire body of work by outlier score. That’s literally how I ran the analysis that opened this newsletter: 105 of my posts, ranked against my own baseline, in about a minute.

2. Extract the subject and the tension, not the format or the words. When my AI-slop posts overperform, the lesson is not “post more screenshots” or “open with a confession.” The lesson is: my audience has an unresolved anxiety about AI writing, and they show up when someone names it honestly. There are probably even deeper insights I could pull, but let's leave it alone for now. The proven thing is the nerve, not the sentence that touched it. This is important to understand because you can return to a nerve forever. But you can only repeat a sentence once.

3. Return to the topic from your current perspective. The topic is public property. Nobody owns “why AI writing sounds hollow” any more than anybody owned “how to remember what you read” or “why consistency beats talent.” What’s yours, the only thing that’s yours, is the angle you have today that you didn’t have last time. For this part, I use Magic Post. I feed it the outliers and use it to break down what’s actually underneath them: the subject, the tension, the nerve, so I’m working with the anatomy of the post instead of just eyeballing it. It’s also where I draft and schedule, so the whole loop lives in one place: outlier goes in, dissection comes out, new angle gets queued. What it doesn’t do, because nothing can, is the next step. Unfortunately, this is where everyone inserts the machine.

And here is where the whole thing breaks

The modern workflow looks like this: find outlier → paste into AI → “write a post like this about my niche” → publish. Tens of thousands of people, running the same method, on the same outliers, through the same model and publishing them on the same platform?

Do you see the problem? If not, you are certainly experiencing it.

The outlier method tells you what to say. But it is structurally incapable of giving you a way of saying it. And when everyone extracts the same proven topics and hands the treatment to the same statistical machine, the outliers stop being outliers, and everything regresses to the mean, because the mean is literally what the machine is built to produce.

Which, and I promise I didn’t plan this, is exactly why my outliers are outliers.

My audience doesn’t overrespond to posts about AI slop because the topic is magic. They overrespond because they can feel the difference between writing that comes from someone and writing that comes from a distribution.

OBERTHOUGHT: AI writing doesn’t sound bad because of the word “delve.” It sounds bad because there’s nothing to delve into.

You can ban every telltale word, and the hollowness will still survive, because the hollowness was never in the vocabulary. It was in the absence of a person with a unique perspective on a topic everyone seems to care about.

So the complete method has a step nobody sells you because it takes work and things that take work are not easy to sell:

The data finds the topic.

The human provides the perspective

And the editing supplies the human.

The first part is research.

The second part is ideation.

The third part is a craft, and it cannot be prompted into existence, because the whole point of it is that it comes from you.

Which brings me to the free webinar

Which is why I’m doing a live webinar with

If you don’t know Taz: he’s the OG LinkedIn guru. As I wrote in the latest Anti Guru Newsletter on LinkedIn, Taz predicted the LinkedIn selfie boom in 2022 and gained 50,000 followers in four months. He told a friend to go all-in on carousels before carousels were a thing. His one self-declared talent is spotting what’s working before the market catches on. So outlier-hunting is essentially his native language, and his new newsletter breaks those down every week.

Taz finds what works.

I make what works sound like a human being wrote it.

That’s the whole Content Hunter method that will make your writing more persuasive and more human.

Together we’re teaching the whole loop: how to write in the age of AI without sounding like every other person using AI to write.

📅 JULY 30th at 8:30 am PST:

Register here (it’s free): https://us06web.zoom.us/webinar/register/8117843441575/WN_Kj5uQvVWSOqsVJHcy_dhPw#/

If your feed feels like it was written by a server in Ohio, come find out why, and how to make sure your writing never joins it.

See you there.

— Justin

P.S If you want to get a head start before the webinar, The Copy Hunter Field Guide is the course version of my half of the stage: 52 hunts for editing anything, yours or the machine’s, until it sounds like a person with a point of view. The first 18 hunts are out. Use the code TAZ to get it for $52 while it’s being built.

Every week, someone asks me the same question.

How do I get AI to write in my voice?

And every week I have to resist the urge to tell them the hard truth directly, because the hard truth is not what they are asking for, because the hard truth is that a voice is not a thing you can capture.

I talk about this in greater detail in my monthly free Idea Hunter Workshop, but to sum it up:

What most people are talking about when they talk about AI copying their writing is AI copying their style, not their voice.

Your style is the surface of your writing. It’s the way you arrange words on a page. It’s whether you use long sentences or short ones, whether you start with a question or a statement, or whether you write in paragraphs or punchy line breaks. In other words, style is a teachable and fixable technique.

Your voice, on the other hand, is something else entirely.

Your voice is the thing attached to your actual thinking. It’s the specific way you notice what’s around you. It’s your tastes, your suspicions, your private opinions about the people you work with, the books you love, the things that genuinely make you angry. More importantly, your voice is what you would say if nobody were watching. In other words, it’s your filter. And a filter cannot be captured because it is not a word pattern.

OBERTHOUGHT: Your voice is a filter, not a style.

Now…

I am talking about voice and style as if they are two separate things, and in one sense they are. But in another sense, when it comes to the writers who actually matter, they are completely inseparable.

Most of You Reading This Don’t Have A Voice (At Least One Worth Cloning)

Whenever I think of someone with a very unique voice and style, I think about the non-fiction and fiction writer Tom Wolfe.

Tom Wolfe had both a voice so singular it could not be mistaken for anyone else’s and a style so distinctive it announced itself from the first sentence of the first paragraph before you even knew what he was writing about.

He used exclamation points the way other writers use periods. He invented compound words mid-sentence when the existing vocabulary was not sufficient for what he was trying to say. He wrote in long, electric, accumulating rushes that felt like someone had grabbed you by the collar and refused to let you slow down. He also borrowed the techniques of fiction, scene, dialogue, point of view, status detail, and applied them to journalism at a time when nobody in journalism thought that was allowed.

But underneath it all was something no amount of technical description or course or even AI training about Tom Wolfe’s style could capture. And that is simply the fact that Wolfe had a specific way of seeing American life, its status rituals, social performance, and desperate and hilarious hunger for prestige, that belonged entirely to him. He could walk into any room in America with his all-white suit and immediately identify its social architecture, who was performing for whom and what everyone was pretending not to want.

Most LinkedIn or even Substack Newsletter writing (hell, even marketing writing of any sort nowadays) avoids any and all of those things.

And even when the perspective is interesting, most of it gets written in a style that makes it seem like it’s trying to be immediately forgotten.

In the 60s and 70s, there were a few copywriters (Ogilvy, Gossage, Bernbach, Halbert, Schwartz) who were known for their voice and style. But nowadays, very few of us actually have a voice (which is a huge mistake when it comes to selling your services as a copywriter, which I will discuss in more detail in my upcoming bootcamp to teach copywriters how to get high-end clients).

To be clear, this isn’t because copywriters are bad writers. It’s mostly because having a voice is not a writing skill. Having a voice is a thinking skill built from years of paying genuine attention to the world around you, forming actual opinions about what you see, and being willing to say what you actually think rather than what the situation permits.

Hemingway had it. His voice came from a specific relationship to violence, to masculinity, to the way men behave when they are afraid, and from a writing discipline so severe it bordered on pathology.

Faulkner had it. His voice came from a specific grief about a specific place, the American South, its beauty and its rot, that he could not stop thinking about, no matter what he was officially writing about.

Bill Bernbach had it. His voice came from growing up a poor Jewish kid from the Bronx in a Non-Jewish world.

Howard Gossage had it. His voice came from a background in promotions and a love-hate relationship with advertising itself.

Tom Wolfe had it too.

And what they all shared was not a technique but a preoccupation, a way of looking at the world they could not stop seeing wherever they looked. In other words, a filter that was so particular to them that the writing it produced could not have come from anyone else.

Even if someone were to copy their style

And I am sorry to say this, but most people writing on LinkedIn or Substack do not have that kind of voice yet.

The Difference Between a Voice and a Style

When you read someone whose writing stops you, it is almost never because of the style. It is because something in the writing reveals a way of seeing you have never encountered in exactly that way. And that could be for a lot of reasons.

It could be because of a specific observation, a particular angle, or a connection between two things that had no reason to be in the same sentence until this person put them there.

Let me show you what I mean with Wolfe specifically.

The title of his first book is: There Goes (Varoom! Varoom!) That Kandy-Kolored (Thphhhhhh!) Tangerine-Flake Streamline Baby (Rahghhhh!) Around the Bend (Brummmmmmmmmmmm).

And this is the opening of Radical Chic, his 1970 New York Magazine piece about a fundraiser Leonard Bernstein threw for the Black Panthers at his Park Avenue duplex. Wolfe was not invited. So he reconstructed the evening from interviews and his own observations of the social world it came from.

At 2 or 3 or 4 a.m., somewhere along in there, on August 25, 1966, his 48th birthday, in fact, Leonard Bernstein woke up in the dark in a state of wild alarm.”

When talking about the event itself, Wolfe describes Bernstein's appearance into the room as if Bernstein was having a vision — seeing himself walk onstage with a guitar.

And then: A guitar! One of those half-witted instruments, like the accordion, that are made for the Learn-To-Play-in-Eight-Days E-Z-Diagram 110-IQ 14-year-olds of Levittown!

The exclamation point after A guitar! Nobody does that. The compound word Learn-To-Play-in-Eight-Days, Wolfe invented it on the spot because no existing word was sufficient to convey the specific contempt he felt for the instrument. The E-Z-Diagram 110-IQ 14-year-olds of Levittown, that is not a description. That is a social class being skewered with surgical precision using nothing but made-up hyphenated words and a zip code.

And all of this is in the first two paragraphs before he tells you anything about the party, the Black Panthers, or any of the famous people who showed up.

He also invents words when existing ones aren’t sufficient, uses exclamation points the way other writers use periods, and writes in long, electric, accumulating rushes that feel like someone has grabbed you by the collar and refuses to let you slow down. He liked to spell out sounds of engines and crowds and laughter because, as he once put it in an interview, “if something sounded a certain way, the writing should sound that way too.”

In The Right Stuff, Wolfe is describes the unspoken caste system among test pilots, the invisible hierarchy that nobody acknowledges out loud but that every single person at Edwards Air Force Base understands completely. But he does not do this by explaining the hierarchy. Nor does he summarize it. What he does is put you inside the social performance of it And then at the very last moment, in the position of maximum emphasis, he names the thing that gives the whole passage its charge: the quality has no name and nobody talks about it:

“A young man might go into military flight training believing that he was entering some sort of technical school in which he was simply going to acquire a certain set of skills. Instead, he found himself all at once enclosed in a fraternity. And in this fraternity, even though it was military, men were not rated by their outward rank as ensigns, lieutenants, commanders, or whatever. No, herein the world was divided into those who had it and those who did not. This quality, this it, was never named, however, nor was it talked about in any way.”

In other words, Tom Wolfe did the thing only he could do: identify the social performance of a room, the gap between what people believe they are doing and what they are actually doing, and put it into a language that makes you laugh and wince at the same time.

That is a voice.

Everything else, the exclamation points, the compound words, the italics, the ellipses, and all the other surface tricks Wolfe fans and critics have cataloged for fifty years are his style.

But a style that belonged to his voice. Because without his voice underneath it, the style is costume. Like his all-white suit.

To illustrate this here is the same scene from Radical Chic written without that filter:

“Leonard Bernstein held a fundraiser for the Black Panthers at his Park Avenue home in January 1970. The event brought together wealthy New York socialites and members of the Black Panther Party. It was considered unusual at the time for people of Bernstein’s social standing to support such a controversial political organization.”

That is what AI produces when you have not given it a mind to replicate.

But if a voice is a pattern of thought, and a thought expressed in language comes out as a certain style, then there must be something in the language that encodes the thinking, something more specific than word choice and sentence length, something that carries the logic of a mind rather than just its surface texture. Something, in other words, that can be copied.

There is.

But before I can tell you what it is, it is very important for me to tell you what it isn’t.

What AI can actually copy, and how to use it

Brook Landon, in Building Great Sentences, makes an argument about language that most people trying to improve their writing will find crazy.

But that is because most people are trained to believe that the basic units of writing are words and sentences.

AI, as a Large Language Model, is trained to think this as well.

But Landon argues that this is not the case at all.

For Landon, the basic unit underlying all writing is not words and sentences, but philosophy, or, to put it, propositions.

For Landon, a proposition is the underlying claim or claims a sentence makes about the world.

These do not need to be complex.

For example, take the sentance:

“After fifteen years in marketing, watching campaigns come and go, sitting in rooms where everyone agreed and nothing changed, I finally understood that the problem was never the strategy.”

That is not one proposition. It is six. The writer spent fifteen years in marketing. Campaigns came and went. They sat in rooms. Everyone agreed. Nothing changed. The problem was never the strategy.

But what I want you to pay extra attention to is what the writer of that sentance chose to put last.

“I finally understood that the problem was never the strategy.”

The whole sentence is a setup for that final proposition, which only lands because the five propositions before it built the room the reader is sitting in when it arrives.

If you move that last proposition to the front, you have a completely different sentance that sounds like a completely different writer. One who, for an infinite number of reasons, has the inclination to announce their conclusion and then explain it.

The propositions are the same. But a sentance that puts that proposition first comes across very differently. It feels different. And the reason it feels different is that it was written in a different style by someone with a different voice. In this case, a voice that comes across as more preachy.

So while one’s style is affected by the way one arranges and chooses the words one puts on a page, it is most affected by the arrangement of propositions that a writer claims, in what order, and with what emphasis.

It is also affected by which propositions they choose to make apparent and which ones they choose to make invisible.

For example, Landon talks about the famous grammatical sentence:

“An invisible G-d created the visible world.”

If I asked you to count the number of propositions in that sentence, you would probably say that there are three.

1. An invisible G-d
2. An invisible G-d that can create
3. A visible world

But one could also say that there were five because the proposition “invisible G-d” assumes that G-d exists. The proposition about a “visible world” also, philosophically speaking, assumes that the visible world exists as well.

You may think I am overreaching here, but this matters a lot if and when I bring these propositions to the surface.

For example:

“There is a G-d! An invisible G-d. That created a visible world.”

Same facts. Same propositions. But a totally different feeling sentence. And all I did was bring one proposition that was assumed to the surface. “There is a G-d.”

The difference between the two sentences is not about vocabulary, grammar, sentence length, or the use of italics or exclamation points.

It is the order and selection of propositions.

It is, in the Tom Wolfe example from The Right Stuff, what Wolfe chose to show you first, what he chose to save for last, what he trusted you to infer, what he named and what he left unnamed.

That is what the protocol below is designed to teach AI to replicate.

Not Wolfe’s voice. Because that cannot be replicated.

But the propositional logic of a specific mind, how it moves, what it foregrounds, what it trusts the reader to supply, and where it places its weight.

And it is the closest thing to a voice that AI can currently produce.

Because the only way to train AI to copy your style (assuming you actually have one) or anyone’s style is to get the AI to look beyond word choice and word arrangements and pay closer attention to the way a person arranges and chooses propositions.

Which brings me to the paid part of this Paid Subscriber newsletter:

The Setup

The protocol behind the paywall below this week is a Proposition Analysis System.

You feed it ten examples of writing from the person whose style you want to replicate. This could be yourself, a client, or a writer you admire. After each example, the protocol dissects the underlying propositions: what claims were made, in what order, what was foregrounded, what was left implicit, what that pattern reveals about how that mind works, and tells you what it has found. This is very important because with AI, there is no input without output. It is also very important for you to review these outputs, as this is not easy for AI to do. It can do it well enough, but it can also sometimes misunderstand or skip propositions. And if you catch that, you need to fix it right away. Otherwise, it will throw the whole thing off.

After you input the ten examples, it synthesizes everything it has learned into a detailed instruction set, detailed enough for you to paste into a Claude Project or a ChatGPT custom GPT and actually produce writing that carries the logical style of the original mind.

It is the closest you can get AI to write in a person’s voice. But I want to be very clear about this…

What it captures is not a person’s voice. Because nothing can capture a person’s voice. All it does is capture the logic and style influenced by that voice.

And that is a very important distinction for you to understand. Because if you copy someone’s style but you don’t actually think in the same way that person does, or provide it with the same kind of detail or ways of thinking that the writer does, the outputs are going to come out sounding very weird.

But when done right, it produces results that are 90% more accurate than everything else people are doing when they try to train AI on someone’s writing.

I have personally used it to create a Claude Project that writes in the style of Tom Wolfe, which (using another one of my protocols that guides me on the information Tom Wolfe needs to write the way he does, plus a little editing afterward) has fooled one or two Tom Wolfe fans and scholars.

I have also used it to create projects for various LinkedIn personalities with unique styles, all of whom, after I showed it to them, asked me for it.

The Proposition Analysis Protocol

The proticol comes in two parts.

Part 1 tells you exactly what this is and how to use it.

Part 2 is the complete prompt, everything you copy and paste.

PART 1: HOW TO USE THIS

What it is: A ten-example analysis system that dissects writing samples at the level of propositions, the underlying claims each piece of writing makes, and synthesizes those patterns into a detailed style instruction for any AI platform.

What it produces: A complete, deployable system prompt you paste into a Claude Project, ChatGPT Custom GPT, or Gemini Gem, one that instructs AI to replicate not the surface texture of someone’s writing but the propositional logic underneath it.

When to use it: Any time you need AI to write consistently in a specific style coming from a unique voice- your own, a client’s, or a writer you’re studying. Run the analysis once. Use the output indefinitely.

How long does it take: Twenty to thirty minutes for the ten examples. Five minutes to deploy the output.

What you need before you start:

Ten writing samples from the person whose style you want to replicate. They do not all have to be in the same format; a mix of posts, paragraphs, and emails often produces a richer analysis than ten of the same thing. Each sample should be at least fifty words. Longer is better. The more the writer has to actually move through an argument or tell a story, the more propositions there are to analyze.

All that matters is that you keep the medium the writing will appear on the same.

If you want the project to write LinkedIn posts, make it 10 LinkedIn posts. For newsletters make it 10 newsletters.

You also want to choose posts that performed well. And by performing well, I don’t just mean from your perspective, but from theirs. You want to find the top 10 examples that performed better than everything else they have ever written. In other words, you want to find the outliers.

To help me find the outliers I use ’s platform Eden.

Among many other amazing things (like giving me a place to store all the content I find online that I find useful or want to refrence, it also allows me to look up anyone with a social media account and, with a click of a button, see their outlier posts. Eden is an essential part of my stack. I have no idea how anyone creating content can create content without it. Check Eden out here.

O.K, back to Proposition Analysis Protocol

What to do:

1. Open a new AI Claude Project, Gemini Gem, or GPTs

2. Copy everything in the box in Part 2 below. The entire box. Nothing outside it.

3. Paste it and hit send.

4. When the system asks for the first sample, paste it in.

5. After each sample, the system will give you its propositional analysis and ask for the next one. Respond with the next sample.

6. After the tenth sample, the system will synthesize everything it has learned into a complete instruction set.

7. Copy that instruction set. Open a new Claude Project, ChatGPT Custom GPT, or Gemini Gem. Paste it as the system instructions.

One honest note before you deploy whatever this produces.

The system you have just created will write in the propositional logic of the person you analyzed. Not perfectly, because no system is built entirely on using language as algebra does. But closer than anything else you have tried.

So the output will be good. Possibly surprisingly good. It will produce writing that carries the logic of the original in a way that surface style analysis never does. But it will still be filled with AI patterns (just styled differently). It will also overemphasize the patterns it was trained to pick up on. It will overemphasize and over-embellish the use of propositions and rhetorical devices, so you will still need to edit it to make it sound more human.

Which is exactly what my Copy Hunter Field Guide for Writing Like A Human in the Age of AI is designed for. It consists of 52 things to hunt for, words, phrases, straw man arguments, big words, etc., to either change or kill.

The first 17 hunts have already been released. When all 52 hunts are made, the price of the Field Guide will be $200. But if you join while we build it, it can be yours for only $75. Just use the word PRESALE at checkout. Here’s the link

And, as I keep reminding you, it will not capture your voice.

Your voice is what you would say if nobody were watching. Voice is the filter. Voice is built from a specific Cabinet of Curiosity, a specific set of lived experiences, a specific way of seeing the world that belongs to exactly one person.

The proposition analysis captures how that person’s mind moves when it writes.

Which is valuable. I think it is genuinely more valuable than anything else I have seen for training AI on a specific writer.

But it is not the same as the voice itself.

A voice can only come from a human being. All the protocol below can do is just make sure that when AI writes on your behalf, it thinks in your direction rather than in the direction of the average.

That is not a small thing.

But it is not everything.

Everything is still you.

PART 2: THE PROMPT

Copy everything inside the box. Paste it into a new AI conversation. Do not copy anything outside the box.

Read more

My Copy Hunte Field Guide for Writing Like a Persuasive Human in the Age of AI is a 52-hunt editing system. Every hunt is a rule: a specific pattern you find in your draft, the word “thing,” the hedging adverb, the AI-flavored opener, and a specific move you make when you find it.

Every hunt is documented, numbered, and extremely teachable.

Which raises an uncomfortable question, one I figured I should ask before a customer did: if the whole system is rules, why can’t an AI just run it?

So I fed the hunts to the machine and told it to edit.

What came back taught me more about writing than building the course did.

The Prompt Everybody Types

You’ve typed it. I’ve typed it.

Make this sound more human.

And the machine obliges in the way it was trained. Em dashes vanish. A contraction shows up. A little fragment gets deployed, like a garnish. And yet, somehow, the result still reads like a machine, only now it’s a machine doing an impression of a person, which is somehow worse than the machine just being itself.

Here’s why that prompt can never work.

An AI writes toward the most probable next word. Which means it is, by construction, an averaging device, the mean of everything everyone has ever written. So when you ask it to “sound human,” it produces its best statistical estimate of the average human.

The problem is that no human sounds like the average human.

Your writing sounds human for the opposite reason: because it deviates. And because behind every sentence there’s evidence of a specific person making specific choices, some of them, crucially, against the rules.

Rules Are for Breaking (After You’ve Followed Them)

But don’t get me wrong.

Good writing follows the rules.

But great writing knows where to break them.

And yes, I know that is cliché.

Everyone nods at that line.

But nobody tries to do it intentionally.

Or think about what that means, which is that a broken rule only reads as a voice if the surrounding writing proves you know the rule. A fragment from a writer in control of their sentences is a choice. The same fragment from a writer who isn’t is a typo. The difference isn’t in the text at all. It’s in the judgment that the text is evidence of.

The problem is that you can teach a rule to anyone or anything in an afternoon. And in time, people can become good at it. But judgment about when to break it is not a pattern. It’s not even really a judgment. It’s a person just writing about interesting things the way they do. And there is no prompt for a person.

What Happened When the Machine Ran My Hunts

Back to my experiment.

The machine ran the hunts flawlessly. Every “thing” was replaced with the noun or idea it was hiding. Every hedge got deleted. Every em dash interrogated. It had one hundred percent compliance on every hunt, every time.

A perfect score.

And what it produced was horrible.

Because its perfect score was the problem.

SO I ran it again and told it to be less perfect.

And the result was even worse.

When a writer runs Hunt 18, the hunt for the word “thing,” they cut nine and keep one because it kinda works there. Because, you know, it was inside a dialogue or the sentance kinda just needed a shrug. For reasons that, for reasons they may not be able to articulate, belong. But the machine, on the other hand, keeps zero. Or it leaves one for a reason it could fully explain.

Perfect compliance and reasoning are the biggest AI tells of all because a draft with every rule followed reads like a form filled out.

The System Works Because You’ll Fail at It

Hand the same 52 hunts to a hundred writers, on the other hand, and you get a hundred different writers, each sharper, cleaner, or more distinct from the others, not less. Because each one, based on an infinite number of factors, breaks rules in different places. Each one keeps a different “thing,” or spares a different hedge, or leaves a different rule unfollowed in a different paragraph.

That’s what makes Hemingway different from Faulkner.

Your tiny inconsistencies are your fingerprint.

And the machine can’t produce that fingerprint because it can’t fail selectively. You can’t help but.

The system works because you can’t run it perfectly.

If you could, it wouldn’t.

Where It Currently Stands

Seventeen of the 52 hunts are uploaded now, with the rest releasing as I finish them. When the course is complete, it will be $250.

While it’s in pre-sale, the code PRESALE gets you in for $75 (which includes everything that’s up now, everything still to come).

Here’s the LINK

And here’s a video intro that explains more.

Permission to Miss

If you buy it, or even if you just start hunting on your own, you’re going to do it imperfectly.

You’ll miss instances.

You’ll keep the hedge you were supposed to cut.

You’ll break a rule in a paragraph where I would have followed it.

And I want you to know that this is a good thing.

Because that uneven, judgment-riddled execution is the only part of the process a machine can’t do, which makes it the only part your reader can’t get anywhere else.

So learn to run the hunts.

Practice them until they become as intuitive as they have become for me.

And don’t worry if you miss a few.

Nobody else will.

In fact, they will probably love your writing even more for it.

-Justin

P.S Yes, I see it: a man selling an editing course announces that AI can’t replicate his editing course. Which is convenient for me. All I can tell you is I tried to automate myself out of the job first, and I’m reporting back that I failed.

I think you should make it your motto as well.

By the end of this newsletter, I hope to convince you why and how incorporating the philosophy of Placet Experieri will change everything about how you think about AI and content creation and help you win at the entire game (because that is what it is) of coming up with ideas to write about.

The Sanatorium Problem

The phrase Placet Experiri was first used by the early-Renaissance Italian scholar and poet Francesco Petrarca.

What I love most about the history of the phrase Placet Experieri is that, despite being renowned for his poetry, Petrarch first used it for a surprisingly practical, literal purpose, in this case, gardening and agricultural grafting.

The exact phrasing stems from a short note written by Petrach, where he was documenting his personal attempts to transplant and graft tree rootstocks and vines. Discussing whether a particular botanical experiment would yield results, he concluded his notes with:

“Sed placet experiri”
(But it is pleasing to experiment / let’s try it out anyway)

It was the German award-winning author Thomas Mann who borrowed it as a major theme for his novel The Magic Mountain, thus turning it into a motto for artists all over the world.

In the novel, a guy named Hans Castorp visits a Swiss sanatorium for three weeks. He ends up staying for seven years. Not because he is or gets sick. But because he is curious.

And as anyone plagued with insatiable curiosity knows, curiosity (real curiosity) is more dangerous than any illness because there’s no cure. Or endpoint. You just keep going deeper.

Now here’s where it gets interesting.

But there are two ways to act on curiosity: one is to keep it in the head. The other is to let it out in the real world.

So Hans Castorp doesn’t just observe the sanatorium or visit and take notes. He submitted to it. He took the temperatures, followed the routines, and tried on every ideology, every perspective, every way of seeing the world that the other patients and doctors offered him.

In other words, he didn’t think about these ideas in the abstract.

He used them and lived inside of them as a kind of grand experiment.

That’s why one of the sanatorium's literary Italian patients refers to Hans Castorp's condition as placet experiri to explain Castorp’s willingness to expose himself to every conceivable influence, ideology, and infection circulating through the sanatorium.

But there is a lesson for us as well.

Especially when it comes to starting your creator journey and figuring out what to create content about in the age of AI.

The Real Problem With Prompts

The trouble with most prompts is the same trouble with most business strategies:

1. They assume the business is a person.

2. They describe the mechanism and ignore the intention.

The enthusiasm for “prompt engineering” is one of the great jokes of our time.

Here we have educated adults (people with degrees, with businesses, with audiences) trying to find the magic words that will make a machine do their thinking for them. So they collect prompts the way people collect recipes, with the unshakeable belief that the recipe is the meal.

But as anyone who has ever cooked anything knows, a recipe is not the same thing as a meal. It’s instructions for someone who already knows how to cook.

Hand a recipe for béarnaise sauce to someone who’s never held a whisk, and you get a warm puddle of curdled eggs. But hand a sophisticated prompt to someone who doesn’t know what they want to say, and for a brief, dopamine-fueled moment, they feel like they’ve accomplished something.

And don’t get me wrong, some people (for reasons that have absolutely nothing to do with AI) do accomplish something with the results.

But most people don’t.

Because what most people accomplish is the digital equivalent of asking a stranger for directions and then mistaking the conversation for the journey.

The whole point of Placet Experiri is to stop talking about the journey you are on and let yourself go on other ones.

As a matter of fact, it was only after letting myself go on such a journey that I discovered the whole philosophy of Placet Experiri to begin with.

The Principle That Actually Works

As I began to write this newsletter, I realized that Placet Experiri not only explains my entire philosophy of how I read books and live my life, but also how I use artificial intelligence.

And suddenly, this newsletter was no longer a pleasant little essay for the free list. It was something rather more ambitious.

It was, I realized, a way of solving a problem I had been circling for months:

How to help people use AI to think better without getting them stuck in overthinking about AI.

As I mentioned at the beginning of this newsletter, one of the reasons I love the phrase Placet experiri so much is that its first use was practical. Even better, its first use is an example of an artistic personality using it for practical purposes.

And the reason I love it is that it should make even the most practical person feel a little more comfortable using it and adopting it as a motto to become the kind of person who does not merely read the menu but orders one of everything, including the items he suspects he or she will not like, because he or she understands (consciously or unconsciously) that the not-liking is itself a form of knowledge.

Or to become someone who reads about a new idea, thinks it’s interesting, but instead of exploring it further like a scholar, decides to try it on, like a costume, to see how it fits, and then posts about it because they agree with it.

When it comes to using placet experiri with AI, the first thing you have to realize is that placet experiri is really more of a principle than a system.

And the principle, explained within the context of using AI to create content, is this:

Don’t use AI to produce content. Use AI to produce depth. Then take that depth and create content with your own voice, your own experience, your own weird perspective that nobody else has.

So I decided to divide this newsletter up into two parts.

The first part (the one you are reading now) is how to use the principle of Placet Experiri with AI, without using any prompts designed to do this for you. While many of the examples I give rely on past prompts I’ve shared, what I am sharing here is really more about me catching myself using AI in a certain way.

The second part (for paid subscribers) includes all the fun, active, and experiential prompts and protocols I use when experimenting with AI.

First, let me show some of the ways I have caught myself using AI while under the spell of placet experiri.

Five Examples of Using AI With Placit Experiri

1) The Depth Proticol

Ask the machine a question. It can be any question related to what you’re building, writing, or thinking about.

Get the answer.

But don’t stop there.

Ask the AI to explain more to go deeper. You can use that phrasing, but it’s even better if you just focus on the most curious thing in the answer it gave you and ask about that. Or, even better, pick one seemingly irrelevant corner of the answer and ask it to tell you more about that. And when it does, don’t stop there either; pick another corner. Go deeper again and keep doing that until the either AI just keeps repeating the same thing or you’ve found something you’ve never thought of or heard before.

This is the technique of the curious child who asks “why?” to every answer until his parents lose their minds. The child isn’t looking for the right answer. He doesn’t even want to see how deep the hole goes. What he or she wants, only they know. Either way, it’s a great way to discover new ideas or techniques to try on.

For example:

Before reading The Magic Mountain, I had never heard of the phrase Placet Experiri. And I only started reading The Magic Mountain because of a hospitality client I am working with who told me that he was trying to come up with some unique ideas for hotel properties. I thought that was interesting, so I started doing some research without asking him. During that research, I read an article about sanatoriums and how they combined the best of health and hospitality. I thought it would be an interesting thing to revive, so I dove into what they were like. After reading refrence after refrence to The Magic Mountain, I decided to give it another go (I was supposed to have read it in college, but never did)

From this reading, I developed an idea to bring back the tuberculosis sanatoria, not as health spas, but as cures for what I, for now, referred to as tuberculosis of the mind. The idea is simple: People who check in will have to check in their phones and laptops and submit to a strict regimen of dopamine detox and rest cures (for 1-3 weeks).

The only reason I am bringing this up is to point out that my hospitality client neither asked me to reread “The Magic Mountain” nor to draft this proposal. In many ways, I wrote it more for myself than for him. I wanted to try my hand at Hospitality, so to speak. See what it felt like to be the kind of person who thinks about these things in these ways. In other words, I was merely practicing placet experiri, a term I would never have come across (or shared with you now) if I had not naturally been practicing it.

2) The Perspective Collision Protocol

This requires a bit more nerve.

Ask AI a question- any question you’re genuinely uncertain about and tell it to answer the question ten different ways.

Not in ten different tones.

From ten different minds.

This works best if you don’t let it come up with random perspectives, because AI is a pattern-recognition machine and will look for patterns.

If you need help coming up with random perpsectives go to an AI you rarely use and ask it to give you a list of 10 random people and professions.

You might get something like:

Seneca
Naval Ravikant
A game designer
A Zen monk
A venture capitalist
etc..

Then go back to your AI and ask it to answer your question as Seneca would. Then as Naval Ravikant. Then, as a game designer. Then, as a Zen monk. Then, as a venture capitalist. Then as Marcus Aurelius.”

What you will get back is not ten correct answers but ten different frames and ways of seeing the same problem.

But it doesn’t stop there.

Because then what you need to do is take the answers that make you most uncomfortable and use them for your content and write them with the confidence you would if they were your actual opinion.

If that makes you uncomfortable, you can say you were considering this solution to the problem and were wondering what people thought.

But the reason why you should do the former is that the ideas that make you uncomfortable might actually be the ideas you also believe. And the best way to tell is if you try them on.

Most people won’t do this because they’ve been trained to project certainty.

But here’s what I’ve learned:

The people who project certainty are trusted. The people who visibly experiment are interesting. And interesting builds a more durable kind of trust, because certainty can be shattered by a single contradiction, whereas a reputation for honest and vulnerable experimentation only grows stronger every time you get something wrong.

3) The Perspective Reversal Protocol

This requires doing the same thing as the reversal protocol, but instead of asking for 10 different answers to a question, you are asking for 10 different arguments against a statement or, even better, something you believe.

Like the protocol above you first get a list of 10 random people or types of people or types of professions. Then you open up your AI and state your position clearly. Then ask the AI to have each personality make the strongest arguments against your statement. Be specific. Ask it not to include any straw man arguments. Tell it you are looking for real arguments from someone at least as intelligent as you who has thought about it at least as long. Some of the people you pick might actually agree with the statement, but may find some problem with the nuance in which you asked it. That’s fine too.

But it doesn’t end there.

After you get the arguments, ask the AI which of these I should be most worried about.

This works better than you might think because AI has no ego invested in your position. It’ll find the holes with the cheerful efficiency of a child pointing out that the emperor has no clothes.

What you do with those holes is your business. But at least you’ll know where they are before your audience finds them for you.

4) The Confession Protocol

One of the most underrated uses of writing (real writing, not AI writing) is the self-discovery it forces you to undergo. You start a sentence not knowing how it’ll end, and when it does, you’ve told yourself something you didn’t know you knew.

And that’s the problem with AI. It destroys this. Especially when you ask it to do the writing.

Try this instead:

Write freely about your subject for several paragraphs. Then paste it into an A and ask it:

“What am I actually saying?

Not what I think I’m saying.

Don’t ask for a summary or the underlying argument or for the thing I seem to believe but haven’t had the courage to state directly.

Be blunt.

“What am I actually saying?

This doesn’t always work, but since AI has no stake in your self-image, which means it can sometimes see what you’re really saying better than you can. Or at least hold up a mirror so you can see it yourself.

When it works, it’s the equivalent of having an honest friend read your work and say, “Yeah, that’s nice, but what are you actually trying to tell me?”

5) The Perspective Reversal Collision Engine Protocol

Take your specific business problem and ask the machine to explain it as though it were actually a problem in a completely unrelated field.

Marine biology. Renaissance architecture. Jazz improvisation. Competitive gaming.

But unlike the Perspective collision protocol, this time you are not asking someone outside to solve your problem. Don’t use the other field as a metaphor. Actually ask the AI to translate the problem into that domain’s terms, constraints, and tools. Have it give an answer in its own terms. Then take that answer and open up another AI (preferably on another platform ) and ask it to use this as an example to solve your business problem.

This works because most problems aren’t unique. They’re local variations of problems solved a thousand times in fields you’ve never explored.

The person who only reads marketing books thinks in marketing clichés. The person who reads biology, philosophy, and game design finds connections that nobody else is making.

And those connections are your unfair advantage.

The Deeper Truth

Here’s what this all comes down to.

The AI is your sanatorium.

If you are sick, you can use it as a place to simply find a cure. Or you can use it like Hans Castorp. As a place with extraordinary resources, contradictory influences, and seductive inactivity disguised as productivity.

And you can stay for three weeks or seven years.

But the only question that matters is:

What are you going to do when you come back down?

Because you will come back down. Everyone does.

And when you do, the world won’t care about what you prompted.

All it will care about is what you made.

People don’t want your best prompt. They want what they want. And your job, the only job no machine can do for you, is to figure out what that is and then to have the nerve to say it in your own voice, with your own peculiar emphasis, to the specific group of people whose attention you’re trying to earn.

That, if you ask me, is the experiment worth running.

Everything else is just typing.

Because the way I see it, there are two types of people using AI right now:

Consumers — who use it to avoid thinking.

Experimenters — who use it to think deeper than they ever could alone.

The consumers will be replaced.

The experimenters will be irreplaceable.

And if you want to become one of the latter, the good news is that the price of admission to experimenting is exactly what Petrarch paid for his grafting notes: nothing. Which is also, not coincidentally, the price of my free monthly masterclass, where I teach you how to never run out of things to talk about. No frameworks to memorize. No optimal posting times. Just the thinking. Consider it your first, lowest-stakes experiment. Placet experiri, after all.

If that experiment works and you develop the nerve I described above — the nerve to try on ideas in public, to say things with your own peculiar emphasis to the specific people whose attention you’re trying to earn- then Mastering the Art of Personal Publicity is where I teach the whole method. Use the code AdvertisingHistory at checkout for 35% off.

And if your problem isn’t the ideas but the writing- that is, if what comes out of the machine still sounds like it came out of a machine my Copy Hunter Field Guide for Writing Like A Human in the Age of AI is where I teach you to fix that. Use the code PRESALE, and it’s yours for $52.

If none of that sells you, then at the very least remember, “Placet experiri.”

It is a pleasure to try.

Who knows what you might discover.

– Justin

Welcome to the Advertising History Today section of the OberThinking newsletter, where I teach about great moments in advertising history, why they are still relevant today, and how you can use them to build your brand or your personal brand.

Tomorrow is the Fourth of July. It’s a big one. America turns 250. And it seems to me that the story we tell about the founding (the soldiers, the statesmen, the self-evident truths) always seems to leave out the two people without whom none of it would have happened:

Which is why today’s issue is about how America Wasn’t just founded by soldiers but was actually launched by a publicist who manufactured the outrage and the copywriter who turned it into a movement.

The Machiavelli of Chaos

On March 5, 1770, in Boston, there was a scuffle outside the Custom House on King Street. A crowd of dockworkers and apprentices started pelting soldiers with snowballs and chunks of ice. After a confused volley of gunfire, five of those colonists lay dead in the slush. It was ugly, chaotic, but by the standards of eighteenth-century urban violence) not particularly unusual.

Within days, however, it had a name.

The Boston Massacre.

The man who defended the soldiers of the Boston Massacre in court was none other than the future second President of the United States, John Adams.

The man who gave it that name was his cousin, Samuel Adams.

And what Sam Adams did in the years between 1770 and 1776 was not, in any conventional sense, political organizing. It was something closer to the most successful publicity campaign in the history of the world.

Samuel Adams was born in 1722, the son of a Boston church deacon who doubled as a political organizer. He went to Harvard, failed at accounting, failed at tax collection, and even failed at what he is best known for today: brewing beer (yes, he failed at the beer business. The brand that took his name was not started by him). So, like most people who end up in advertising, publicity, or politics, he drifted irresistibly toward the one thing he was genuinely brilliant at: making people care about things they had not previously cared about.

He began writing for the Boston Gazette, where he wrote under more than thirty different pseudonyms such as Candidus, Vindex, Populus, Determinatus, and dozens of others.

And he didn’t write under those names one issue at a time, but all at once.

A reader of the Gazette in the mid 1700s could be forgiven for thinking that outrage at British taxation was a universal sentiment, because everywhere they looked, a different writer was expressing it. That all those writers happened to be the same man, sitting in the same room, dipping the same pen into the same inkwell, was something the public did not need to know.

This was content strategy in its earliest, purest, and most Machiavellian form. A single voice arguing for liberty could be dismissed as a crank. But thirty voices, all apparently independent, all arriving at similar conclusions from different angles? That was a movement. Or at least it looked like the beginnings of one. And in the business of public opinion, looking like a movement and being a movement are (for all practical purposes) the same thing.

A Picture Worth A Thousand Words

So when the King Street shooting happened, Samuel Adams recognized the opportunity immediately. A skirmish that would have been forgotten in a week became, through his intervention, a defining atrocity.

Calling it a massacre implied premeditation, savagery, and that the victims were innocent and the perpetrators were monsters. None of this was entirely accurate. As his cousin John Adams proved it court, the crowd had been aggressive, the soldiers had been provoked, and the commander had not ordered anyone to fire. But Sam didn’t care what the court of law said. He only cared about the court of public opinion. And on the court of public opinion, accuracy is not the point.

In addition to calling it a massacre, he commissioned Paul Revere (yes, the same one who warned that the British are coming) to alter and engrave a depiction of the event drawn by a young Boston artist named Henry Pelham and had the resulting engraving printed and distributed across the colonies.

Like Pelham’s illustration, Paul’s engraving showed an orderly line of British soldiers, their captain’s sword raised in command, firing deliberately into a crowd of well-dressed, unarmed civilians. But in Paul’s etching, The Custom House was labeled “Butcher’s Hall.” Also, the sky is clear and bright (the incident had occurred at nine o’clock at night, in a snowstorm). Every element of the image was recalibrated to produce a single emotional response: horror.

It was also, as any modern advertising professional would recognize, spectacularly untargeted.

The engraving was not directed at legislators, diplomats, or military strategists. It was directed at everyone. It was distributed to anyone who would look at it. Its power lay not in precision but in reach, not in its ability to convert a specific audience but in its ability to make the event famous.

And fame, as any student of brands will tell you, is the first and most fundamental form of value in any act of commercial or political persuasion.

America’s First Content Distribution Network

But Sam Adams didn’t stop at branding and visual assets. He built the infrastructure.

Before there were newspapers in every town, before there were telegraph wires or postal routes that could carry ideas at speed, Adams built a system that ensured his version of events (and it was very much his version) reached every corner of the colonies.

In 1772, he organized the Committees of Correspondence: a network of local groups across the thirteen colonies whose purpose was to share information, coordinate responses, and (let us be honest about this) distribute propaganda. Each committee published writings listing colonial grievances. Each was connected to the others. Information that originated in Boston could reach Virginia within weeks.

This was, in effect, an early form of what we now call a content distribution network. A topic that we will be talking about a lot more in my next Anti-Guru Newsletter

The Committees did not merely inform. They shaped the narrative and ensured that when events occurred in one colony, they were understood in every other colony through a particular lens.

The Boston Tea Party, which took place in December 1773, when three hundred and forty-two chests of East India Company tea were dumped into the harbor by men dressed as Mohawk Indians, was the culmination of this approach.

Despite what the history books make it feel like, it was not a spontaneous uprising. It was a piece of planned political theatre, meticulously staged by Adams and the Sons of Liberty, and designed at every level to be talked about. The Indian costumes were not such that Indians would be blamed. They were an unusual detail that made the event memorable (and shareable, in the language of a later era). The act of destruction was the content, and the outrage it provoked was the distribution. And the story (brave colonists defying a tyrannical tax) was the brand.

The Copywriter Who Arrived with Nothing

If Sam Adams was the publicist who manufactured the crisis, Thomas Paine was the copywriter who sold the solution. And his story is, in some ways, even more improbable.

Fourteen months before he gave the world some common sense, Paine, like most copywriters before they wrote the thing they became famous, was a nobody. He was a failed corset maker and twice-fired tax collector from Thetford, in Norfolk. Paine was also a man whose life bore his name. His first wife had died, and his second marriage had collapsed. When he arrived in Philadelphia in November 1774, he had nothing to his name but a letter of introduction from Benjamin Franklin, whom he had met through a chance connection in London.

Thanks to that letter, he got a job editing a magazine and started writing political pieces for local newspapers under his own name. And on January 10, 1776, he published a forty-seven-page pamphlet called Common Sense.

At first, he simply signed it as “An Englishman” for political and safety reasons.

It sold (by Paine’s own estimate, which was almost certainly inflated, though the true figure was still staggering) 120,000 copies in its first three months. Twenty-five editions appeared in the first year alone. An estimated 20 percent of the colonial population owned a copy. Adjusted for today’s population, that would be roughly sixty million copies, which makes it, even by today’s standards, one of the best-selling American publications ever written.

Paine eventually revealed his identity a few months later, in the spring of 1776, as the colonies moved definitively toward a split from Great Britain.

He chose to come forward because the pamphlet’s runaway success made the secret difficult to keep and because he wanted to openly take credit for the movement he had galvanized. By stepping forward, he proudly aligned his actual name with the cause of independence and embraced his newfound role as a leading revolutionary voice.

Nowlet’s talk more about that voice.

On the Art of Speaking Painely (I mean Plainly )

Common Sense was not the first argument for independence ever written. Sam Adams and his cousin John Adams, along with Richard Henry Lee and others, had been making the case privately in the Continental Congress for months. The intellectual groundwork had been laid. The grievances were well known.

What did not exist was the language.

Most pamphleteers of the era wrote for lawyers. They cited Cicero and Montesquieu. They deployed Latin phrases and constructed elaborate legal arguments rooted in the rights of Englishmen. They were writing, in effect, for each other: that is, for educated men in wigs who could follow a syllogism across three subordinate clauses and still remember the premise.

Paine wasn’t one of them, so he didn’t write for them.

Instead, he did something radically different.

He wrote for farmers and dockworkers.

He used short sentences, plain words and the rhythms of the King James Bible (which by today’s standards would seem too formal but back then worked because that was the one book every colonist had actually read).

He also took chances where most upper-class writers wouldn’t because they had too much to lose.

He called the king a “royal brute” and wrote sentences like: “There is something absurd in supposing a continent to be perpetually governed by an island.” And: “A long habit of not thinking a thing wrong gives it the superficial appearance of being right.”

He offered, as he put it, nothing more than “simple facts, plain arguments, and common sense.”

And the colonies, which had spent a decade arguing about taxation and representation and the finer points of constitutional law, shifted (in roughly six months) from “we’re angry about taxes” to “we want independence.” Not because the argument changed. But because Paine had the unique gift of feeling the pain of ordinary people and giving them a version of the argument they could understand, repeat, and feel in their bones.

John Adams, who resented both his cousin Adam and Paine personally, and disagreed with their politics, admitted it unusually plainly (or should we say Painely:

“Without the pen of the author of Common Sense, the sword of Washington would have been raised in vain.”

And there is no doubt that Paine’s language influenced John Adams, Thomas Jefferson, and Benjamin Franklin when they sat down to write the Declaration of Independence. A fact that was beautifully dramatized in this surprisingly accurate depiction of the creative process behind the writing of America’s Declaration of Independence from HBO’s biopic: John Adams.

It’s also a great depiction of what most ad agency creative review meetings sound like.

Watch it and imagine:

The Continental Congress is the client.

Ben Franklin is the Creative Director.

John Adams (played by Paul Giamatti) as the Account Director .

And Thomas Jefferson was a young hotshot copywriter with big ideas and elegant writing.

As Paine proved, good ideas and copy are not sacred and undeniable.

They are self-evident.

And yes, Thomas Jefferson did invent the swivel chair to write the Declaration of Independence.

Copy as a Weapon

In December 1776, the revolution was failing. Washington’s army had been routed in New York. Soldiers were deserting, and enlistments were expiring. The cause was, by any reasonable assessment, close to collapse.

So Paine wrote a follow-up pamphlet. The first installment of The American Crisis. It opened with thirteen words that may be the most effective piece of crisis copywriting ever composed:

“These are the times that try men’s souls.”

Washington, on the eve of a battle that would determine whether the revolution would survive or die, had the pamphlet read aloud to his freezing, demoralized troops on the banks of the Delaware River, the night before the crossing to Trenton.

The soldiers crossed that river. And the revolution survived.

What These Lesser-Known Founders Can Teach You About Content

As I have already mentioned, tomorrow is the 250th anniversary of the nation they helped create, and partly because it seems to me that what they did (together, though they would not have thought of it that way) constitutes the most complete case study in publicity and copywriting that history has produced. Neither of them signed the Declaration of Independence or was involved with the Constitutional Convention.

But make no mistake about it, without them, a lot of it would not have been possible.

Consider what Sam Adams understood.

He understood that events do not speak for themselves. That they must be named, framed, and distributed. A shooting becomes a massacre. An engraving becomes an icon. A network of letter writers becomes a movement. He understood that the raw material of experience means nothing until someone shapes it into a story that people can feel, remember, and repeat. You may not be trying to overthrow a government, but this applies to you to because this is what the best marketers and publicists do. And this is what the best personal brand builders do too. They do not wait for the world to notice them. They take the raw material of their expertise and shape it into something that travels.

If you’d like to understand more about how Sam Adams came up with his ideas, I’m running a free monthly masterclass on How to Never Run Out of Ideas Without Relying on AI. It’s live, it’s practical, and it draws on the same principles Adams understood two and a half centuries ago: that the best content comes from having a genuine point of view and the discipline to express it clearly. Grab as seat here.

If you’d like to learn more about the publicity techniques so that you can use them for yourself, my Mastering the Art of Personal Publicity course is built around the same principles Sam Adams used to make both himself and his cause impossible to ignore. Use code ADVERTISINGHISTORY for 35% off. Enroll here.

Now consider what Paine understood.

He understood that the most important audience is not the small class of sophisticated people who already agree with you. The one with a shared language that doesn’t sound human to others. Paine understood that the most important audience was made up of the people who feel the same way but just haven’t heard the argument in words they can feel. That’s why, while every other pamphleteer in America was writing for other pamphleteers, Paine wrote for the people who would actually have to fight the war: farmers, tradesmen, apprentices, mothers. So he wrote the same thing everyone else was writing, but in plain language, not because he lacked sophistication, but because Paine had the unique gift of feeling the people’s pain. His failures and tragedy gave him an abundance of empathy. He knew his reader. He respected his reader. And he trusted that if the argument was clear enough, the reader would do the rest.

This is, it seems to me, the single most important lesson for anyone writing content today.

Don’t write for other content creators. Or the algorithm. Or for the people who already follow you. Write for the person who understands the argument but has never heard it put in a way they can grasp it yet. Who has never heard of you, who is scrolling past, who has three seconds to decide whether you are worth their attention. And the only way to win those three seconds is to write with the clarity and conviction of a man who knows his reader’s life depends on understanding the argument.

And for any copywriter trying to build a business for themselves in today’s crazy world, remember: Paine arrived in Philadelphia with nothing. No credentials. No following. No reputation. Just a letter of introduction from one important man (which is important and you should seek as well) and the ability to write a sentence that landed. And yet, within fourteen months, he was the most widely read author in America. But Paine did not build his audience through networking, positioning, or brand strategy. He built it by doing something. And in this case, by writing something so clear, urgent, and impossible to ignore that the audience built itself.

If you want to write like Paine, that is, if you want to write like a human in the age of AI, my Copy Hunter Field Guide for Writing Like A Human in the Age of AI is on presale now. It’s a field manual filled with 52 hunts you can apply to anything you write (or that is written for you) to make it sound more human, designed for anyone who wants their writing to sound like them, not like a machine. The first 15 hunts are already out. Use code PRESALE for $52 before the price goes up after completion. Get it here.

Anyway, in conclusion...

I’ve spent over 25+ years in the idea business. As a copywriter, creative director, and now as a creator, my job has always been to come up with ideas all day long.

To do this successfully, I’ve come to accept two things.

The first is that no idea is perfect.

There’s always something that’s a little off brief or a little challenging.

The second is that even the best ideas are never executed perfectly.

There are just too many players at stake.

But none of this means a good idea isn’t good or the best one for the job.

Tommorow is July 4th. It is also America’s 250th birthday.

It’s a good time to remember that before it was a country, America was an idea.

Not a perfect idea. Because I have just said, no idea is. Nor a perfectly executed one.

Name one that was?

But I still think the value of the ideas made possible by the publicizing and writing of Sam Adams and Thomas Paine holds up:

1. That all people are created equal

2. That everyone is endowed by their Creator with certain unalienable Rights and

3. That among these are Life, Liberty, and the pursuit of Happiness.

But all this is based on an even bigger idea:

The willingness to encourage, express, and accept new ideas.

For me, July 4th isn’t a day, a flag, or a country.

It’s an idea.

Specifically, it’s an idea based on the ability to change ideas and even create new ones.

I don’t think there is a country on earth that makes that more possible than America.

And I don’t know about you, but as a creative, that sounds like something worth celebrating.

Sam Adams understood how to distribute that message

Paine understood how to talk about it.

Together (without ever consciously collaborating), they proved that publicity and copywriting are not separate disciplines but can be two halves of the same act: the act of making an idea famous enough and clear enough that it changes what people believe.

May this newsletter inspire you to do the same.

Happy July 4th, everyone!

Justin Oberman
Follow me on LinkedIn

There was a post going around on LinkedIn from a woman who watched her boyfriend write something by hand at the airport with no wifi, cell service and therefore no AI. She was shocked when it still read like AI. Her conclusion was that AI is rewiring the way we write.

Wrong.

Because that is the way amateurs always wrote.

The only thing it genuinely changed is volume.

You can now produce ten drafts in the time it used to take to write one. But ten bad drafts faster is not an advantage. The advantage only shows up if you edit the content yourself

Everybody has a writing machine now.

And everybody is getting caught using it.

You paste your post. It reads fine to you. Then somebody drops a comment under it: “Did AI write this?” Or worse, nobody comments on anything. They just scroll past because something about it smelled like a press release, and their thumb kept moving before their brain could explain why. Or worse still,m AI’s algorithm detects it and smothers your post.

In this newsletter, I want to discuss:

• Why AI doesn’t write badly. It writes like an amateur (and why that’s worse).

• The one writing skill that survived the AI apocalypse.

• The slippery slide, and why your reader is always hunting for an excuse to quit.

• Six hunts you can run on your own copy today.

• Where to learn the whole system for $52 before it becomes $250.

AI Writing Slop Is Not New

Mediocre writing used to be boring.

Now it’s suspicious.

The machine didn’t just make writing easier. It made average writing radioactive, which has made everyone more vigilant, and the moment a reader suspects a sentence came out of a model, the appearance of truth vanishes, and with that, so does their attention and trust.

But here’s the uncomfortable thing I’m going to argue in this letter:

AI did not make people worse writers.

It just revealed that most people were never good writers to begin with.

Because at the end of teh day, when you really analyze it, AI writes as the average person writes. Which is to say, it writes like an amateur. It adds the same padding, the same throat-clearing, and buries the same leads as amateur writers do.

The antidote for this is obvious.

The more interesting ideas you give it with greater detail, the better the output.

That part should never be automated. And it is probably the most important part of writing, which is why I teach How to Come Up With Infinite Ideas to Write About for Free Every Month (here)

But there’s another part of writing that shouldn’t get automated either. One job that still belongs to a human and always will. It’s not the typing of the actual words. It’s the editing. And once you understand why, you stop competing with ma machines and start using it like a professional. writer

Let me show you.

AI Doesn’t Write Badly. It Writes Like You Used To.

Right now there’s a war on your feed.

One camp post:

“Never let AI write your content.” They share their little one-pagers on how to stay pure.

The other camp quietly runs everything through a model at 11 pm and ships it anyway.

But real writers know that that war is a distraction. What’s actually true is that before AI, when the average person sat down to write instead of speaking, something switched in their head. They suddenly believed they had to become more articulate. More formal. More “writerly.” So they do things like pad sentences by announcing things like: “Let me walk you through this.” or “Let me make myself clear.” (If it was clear, you wouldn’t have to say so.) Or they would bury the real point seven lines down, because they feel they have to earn it first with a paragraph of warm-up nobody asked for.

And because that is the majority of the kind of writing that is out there, AI inherited it as its default.

This is why uninstructed AI writes like an untrained writer. Which, before AI, was not a bad thing, but post-AI has been amplified to the point of nausea. But even instructed AI mostly writes like an amateur. This is why it reaches for adjectives like “quietly” and “tapestry” and “underscores something deeper.” Because you didn’t give it anything specific and true to say instead. So it pads the hole with a pretty word.

The problem with this is that most people are not professional writers.

So when the machine hands them a draft, they read it and think it’s good. Because it’s exactly what they would have written themselves. The mediocre writer reads mediocre output and feels seen. So really, nothing changed. It’s just been amplified.

You’ve watched this happen in real time. You read a post from a “social guru” teaching people how to automate their content and every line is exaggerated with every detail supposedly underscored by something deeper.

But nobody talks or thinks like that.

Nobody has ever talked or thought like that.

Why You Should Let AI Write For You

The old way of writing had three jobs that, in a way, required three separate skills.

1. Figure out what to write about.

2. Sit down and actually write it.

3. Edit it.

The new way has 1.5 jobs.

1. Figure out what to write about (with the help or without the help of AI

2. Let the machine generate the raw material.

3. You edit it

AI is very good at removing the physical labor of things. And believe it or not, despite everything I’m saying, that means I actually think that there is no problem at all with having AI do the actual writing for you.

A few people agree with me. They refer to what AI writes as a first draft that a person edits.

But that is not what I’m talking about.

Because when AI (or the average person writes something, what it or he or she produces is not a first draft.

It’s garbage.

I mean that as a technical term, not an insult.

But garbage that happens to be a lot easier to fix than a blank page.

And that’s why, when you first start working with anything that AI produces, you shouldn’t treat it like you are editing a first draft. Rather, you should look at it like you are hunting.

How to Go Copy Hunting

The human brain doesn’t want to read. Even things that it is interested in. It will literally look for any excuse to stop reading.

This is why the legendary copywriter Joe Sugarman described great copy as a slippery slide. The only job of your first line is to get the second line read. The only job of the second is to get the third read. And so on, until the reader forgets they’re reading at all and just slides.

The small details that keep a reader sliding are the small details that separate good writers from great writers.

This is even more important in marketing writing, where a combination of entertainment and persuasion is essential.

And the way that you write like a great writer is not by actually writing the words well, but by hunting for these small details in a series of small hunts.

You go through your copy, hunting for one specific thing at a time. You find it. You kill it, or you fix it. You move to the next hunt. That’s it. That’s all it takes to take the vague terror of “make this better” and turn it into a checklist you can actually run at 11 pm without a muse showing up.

Here are 4 examples of AI-specific hunts:

Hunt 1: The buried hook

We all bury the lead. All of us. We clear our throats for a paragraph because we think we have to warm up before we’re allowed to say the real thing.

Your actual opening line is usually about seven lines down. It’s the line where you finally stop performing and just say it.

Go find that line. Cut everything above it. Watch what happens to the post.

Hunt 2: Adjectives

Take the sentance, “The car is quiet.” The word “quite” is an adjective that tells the reader what something is without helping them feel it.

Ogilvy didn’t write “this Rolls-Royce is quiet.” He wrote: “At 60 miles an hour the loudest noise in this new Rolls-Royce comes from the electric clock.” You don’t just learn it’s silent. You feel it.

So hunt for adjectives and ask whether or not you can replace it with a fact that shows the same thing. Because the more specific the detail, the more it shows, and the more it’s believed.

So instead of saying “I’m fast.” Write “I can do it in under two hours.” This, by the way, is why AI reaches for empty words like “quietly.” You probably didn’t give it enough details, so it grabbed an adjective. Give it more facts, or supply the fact yourself in the edit.

Hunt 3: The padding

“It’s important to remember.”

“Let me walk you through this.”

“What this really means is.”

“In conclusion.

Hunt every phrase that announces what you’re about to do. Then get rid of it so that you are just doing it.

Let me make this perfectly clear.

If a thing is clear, you don’t need to say “let me be clear.” And if what you said wasn’t clear, fix it so it is, instead of apologizing for the last one.

In other words…

Delete the announcement. Keep the thing it was announcing.

Hunt 4: The tells

You already know the flagged vocabulary. Tapestry. Delve. Intricate. Foster. Hunt them, but instead of replacing them with other words in a thesaurus, replace them with how an actual person would say it.

So instead of “That’s a tapestry of ideologies,” say, “There are many different ways of thinking going on at once here.”

Now, about the em-dash.

I belong to the camp that says to remove them.

I don’t care if you used them before or if it actually makes sense to use them where you are using them. None of that matters. Today, when people see an em dash, they immediately get the feeling that it was written with AI. And once they feel that the appearance of truth collapses, they stop reading. Your job as an above-average writer is to make sure the reader never stops reading. So if the em dash gives anyone a single excuse to quit reading, cut it. I avoud using semi-colons for the same reason. Not because AI uses them., It doesn’t. But because most people don’t know how to use a semi-colon. So when people read a sentance and come across a semicolon, they stop and think, “How am I supposed to read this?” So if a punctuation mark hands anyone an excuse to stop reading, you hunt it and kill it.

Why AI Can’t Make AI Content Sound Human

The logic of asking something that is not human to sound human should be enough to convince you as to why AI can't write or edit its own writing to sound human. But just in case you need further proof, here they are.

You can’t ask the machine to make its own writing sound human, because…

1. The thing that makes writing sound human is judgment, and the machine doesn’t have any.

2. AI’s only “understanding” of anything is based on language. That’s why they call it a Large Language Model. But, believe it or not, language is not how human beings think. You may think it’s how we think, but it’s not. And the proof of that is a newborn baby.

3. AI was trained on amateur writing, so its instinct for “better” is more polish, not more truth. Ask it to humanize a draft, and it just sands the edges, swaps a few words.

4. AI has no feelings (both literally and emotionally). This is why the only AI detector that works is a person, and why a person isn’t fooled by smoother syntax. Because they can feel when nobody or nothing is behind the words.

5. Running an AI draft back through the AI to make it “sound human” is literally the definition of an open loop.

6. AI and LLMs are pattern recognition machines. Human writing is sloppy and breaks patterns. It doesn’t write in them.

7. Human stuff has to come from a human.

8. Even if one were to create rules of human writing, great human writing breaks rules, which requires someone who knows what to keep, what to kill, and what’s missing based on feelings, not rules.

9. AI can’t sound human because, having never truly been a human, it can’t know when it does.

10. There is more to writing than just the words.

11. AI output can sound human, but only when a human with taste edits it.

12. AI detectors are garbage.

The skill nobody can take from you

You can’t beat AI detectors.

They flag perfectly good human writing as machine-made all the time, and they will never tell you their formula, partly because they don’t fully know it themselves.

So, I can’t guarantee that these hunting techniques will get you through AI detectors.

But they will greatly improve your odds.

AT the end of the day, the best AI detector that exists is you, a human being.

We are great at spotting it in other people’s writing. But we suck at finding it in stuff generated for us.

So the goal of Copy Hunting is not to get a green checkmark on some tool. Your goal is to end up with writing that a person never once suspects or cares if a machine had anything to do with it.

And when you run these hunts enough times, on enough pieces, the strangest thing happens.

The machine becomes training wheels you eventually outgrow, and you stop needing the AI draft at all.

You catch yourself thinking it would be faster to just write the thing, go on a quick hunt, and then edit it. When that happens, that’s how you know you’ve actually mastered the hunts.

The future of writing post-AI.

The skill of the next decade isn’t writing. Everyone can write now. AI handed the whole world a typewriter that never gets tired.

The skill now is taste, expertise, creativity, and the editorial judgment to look at a wall of generated text and know instantly what to keep, what to kill, and what’s missing. And that editorial judgment can’t be prompted or downloaded.

It’s the last part of any creative endeavor that guarantees whatever it is you create is unmistakably yours.

So.

Stop outsourcing the last part that matters.

Stop publishing the first thing the machine hands you.

Or tinkering with it before it goes out.

Stop trying to sound articulate and start trying to sound like a person who actually knows what they’re talking about.

Learn to hunt.

To help, I took everything I have learned about editing copy and created The Copy Hunter’s Field Guide to Human Writing

It is not a writing course.

It’s an editing system.

And at the present moment, it’s a growing library of what will eventually become 52 individual hunts taught with real before-and-afters so you can understand exactly what moved and why.

I really want this to be an easy and useful tool that makes you less dependent on AI so I am building it slowly.

The first 10 hunts are live right now, plus the foundational pre-hunt videos that set up the whole method. I’m building it in public. New hunts drop regularly, and it’s going to grow to a full 52. And because it’s still being built, you can get in right now for $52 instead of the $250 it will become once it’s finished. That’s a dollar for every hunt that’s coming. You lock that price, you get everything new as it lands, and you get to start running these hunts on your own writing starting today.

→ Use the code PRESALE and get The Copy Hunter’s Field Guide for $52

Hunting is Not All It Takes

One honest caveat, because I’d rather lose the sale than lie to you.

Editing cannot save a bad message.

No amount of hunting makes the wrong offer land with the wrong person. The power of all great writing lives in what you’re saying and who you’re saying it to, not in how you say it. No matter how smooth, human, and conversational the sentences are. You cannot make people who don’t want ice want more ice. The hunts are what separate the professional from the amateur after the message is already right. Nothing more

So the most important skill is still knowing what to say. Which is exactly what I teach in my free monthly masterclasses about How to Never Run Out of Ideas to Write About Without Relying on AI. Attendance is capped at 32 people. And it always is, so → Save your seat for the free July masterclass

That’s it for this letter.

Go hunt some words.

– Justin

On Tuesday I published a manual for becoming worse at artificial intelligence, and a gratifying number of you were annoyed by it.

Good.

I have never written anything with the primary aim of being welcome, and I am too old to begin now.

But a smaller and more interesting number wrote back with a version of the same objection, and because it is the honest one, I want to take it seriously. It went roughly like this: I would love to become worse at this. I cannot. My rent runs through the machine. My clients expect the velocity. You are asking a man to surrender the very thing that feeds him and calling it freedom.

Fair enough.

Tuesday’s letter was, I will admit, the easy half of the argument. It was a manual of abstention, write the thing yourself, put the friction back, read the book instead of the summary, sit in the silence, recover your boredom, keep one room of your mind the machine never enters. All true. All useful. And all, for the working professional with a mortgage and a content calendar, about as practical as advising a drowning man to take up residence on dry land.

So this letter, which is for the people who have a paid subscription and are therefore owed the harder and more useful half, is about the other thing. It is about how to go on using the machine, daily, heavily, without apology, and use it, deliberately, to become worse at needing it.

Subscribe now

This Is Not Permission to Use It Badly

This is not about using AI badly.

First off, if you use AI badly, then you are probably not the kind of person who is worried about becoming worse at it. And that is fine. Because using AI badly, sloppily, lazily, with a shrug, is not rebellion against the machine. It is the automated man’s same surrender, performed with worse manners. Slop is not made any better because of the moral conviction behind it. Slop is slop. Creating slop on purpose improves nothing and fools no one for long.

What I am describing is the opposite of carelessness. It is using the machine on purpose, and strategically, and with a great deal more thought than the efficient man has ever troubled to bring to it in order to figure out how to use it less.

And you do this by aiming the most powerful labor-saving device ever built at the one task the people building it didn’t intend for you to use it: making you slower, and more competently incomptent in exactly the places where slow was always the whole point.

You Are What You Ask For

Every prompt you write trains something. Not the machine, let’s leave the machine’s training to the people in Northern California who are paid handsomely to lose sleep over it. I mean, it trains you. The man or woman who spends two years asking a machine for finished outputs is, whether he intends to or not, conducting a long and patient program to teach himself to want finished outputs and nothing else, until the wanting of anything slower or stranger or more effortful comes to seem faintly absurd. He has not merely used a tool. He has let the tool file down the part of him that used to do the work, the way a right-handed man’s left hand, never once asked to do anything, quietly forgets how.

Which means the strategic question is not what this thing can do for me. It is what this particular use of it is doing to me. Ask the machine for an output, and it makes you a man who needs outputs. Ask it to resist you, to interrogate you, to carry you somewhere you have never been, and then leave you stranded there, and it makes you, slowly and against the prevailing wind, a mind again. Ask it if it’s really the best tool for the job, and you’ve just received an upgrade that most people using AI will never achieve.

Why?

Because the machine is morally neutral. It is a mirror with a motor. It will accelerate you toward whatever you keep pointing it at, which means if you point it toward its own obselence in your life, you will be delighted by how quickly that comes to pass.

* * *

Four Ways to Aim the Machine at Yourself

The Way Everyone Aims It: The Adversary. In another newsletter about how AI works I pointed out machine has no point of view, only a statistical average of everyone’s. That is precisely what makes it the finest sparring partner you will ever hire and the worst possible collaborator. So stop collaborating with it. Forbid it, in plain words, to write your thing, to agree with you, or to improve your draft. Give it one job: attack. Tell it to find the cliché you are about to commit, the assumption you have not examined, the objection your smartest competitor would raise, the spot where your argument is wearing a borrowed suit. Then make you do the answering. You will be using the machine as intensively as ever, but every exchange now forces you to produce the material, because the only thing it is permitted to produce is trouble.

Try this: “You are not my collaborator, and you are forbidden to act like one. Do not write this for me, do not rewrite it, and do not tell me it’s good. Below is [my draft / my argument / my plan]. Your only job is to attack it. Find the laziest assumption I’ve made, the cliché I’m one sentence away from committing, and the single strongest objection a smarter, better-read competitor would raise that I have not answered. Be specific and be unkind. Do not offer fixes — I’ll handle those. Just show me where it’s weakest. [paste your work]”

The Way Students Aim It: The Tutor: On Tuesday, I asked you to sit with a question and not reach for the machine, to let yourself not know, on the grounds that not-knowing is the doorway to curiosity, and curiosity is the doorway to everything worth having. Some of you found that unbearable. Fine. Here is the paradox for the unrepentant: reach for the machine constantly, but order it never to answer. Instruct it that whatever you ask, it may reply only with a sharper question, or by handing your own question back to you reframed, until you have done the answering yourself. It becomes the Socratic tutor who drags the knowledge out of you, which, if you remember your Plato, was the only kind of teaching he thought deserved the name.

Try this in a project: “For this entire conversation you are forbidden to give me answers. No matter what I ask, you may respond only with a better question, or by handing my own question back to me sharpened. If I try to bait you into answering, refuse, and ask me what I think instead. Do not stop until I have worked it out myself. My question is: [your question].”

How Experts Aim It: The Foreign Correspondent. Tuesday’s diagnosis you may have found insulting: that the man who outsources his thinking is the most provincial creature alive, a man who has narrowed the whole world down to a single source and mistaken it for the world. Here is the cure, and it uses the very machine that caused the disease. Stop asking it for answers inside your own trade, where it only feeds your trade’s exhausted clichés back to you. Send it abroad instead. Use the machine as a passport to new destinations. Let it carry you to the border of a country you have never entered. But beware. It cannot do the entering. That part is still done on foot. Start here, or try the below:

Try this: “I work in [your field]. My problem is: [state it plainly]. Do not solve it in the language of my field — I already know those answers and they bore me. Instead, explain my problem exactly as it would be understood by [a marine biologist / a cathedral architect / a general losing a war / a jazz musician], using that discipline’s real concepts and constraints. Then translate the insight back to my situation. Finally, name three real books — not summaries — that someone serious in that field would consider essential, so I can go and read them myself.”

How Writers Aim It: The Confessor. Ideally, you would apply my Copy Hunting Technique to anything you write (use code PRESALE to get it for $75). But this aim builds directly on the first technique from Tuesday, so do this one first: write the bad draft yourself, in your own clumsy voice, before the machine lays a finger on it. Now bring the machine in, and do not, under any circumstances, ask it to rewrite you. Ask it instead the one question your friends are too kind to answer honestly. The machine holds no stake whatever in your good opinion of yourself, which is its great defect as a flatterer and its great virtue as a reader. Used this way, it does not replace your voice. It locates it, usually about four paragraphs down, hiding behind the throat-clearing.

Try this: “Below is something I wrote myself, before showing it to you. Do not rewrite it, do not polish it, and do not compliment it. Tell me what I am actually saying — not what I think I’m saying, not a tidy summary. What do I appear to believe here that I haven’t had the nerve to state outright? Where am I hedging? What is the real argument hiding under the throat-clearing? Be blunt. [paste your draft]”

How To Use These Aims Together

When I called what the machine does to your mind atrophy, I meant it as physiology, not metaphor. And the thing about a wasted muscle is that you do not bring it back by resting it. You bring it back by loading it — by making it work against a resistance heavy enough to hurt. That is what the four uses above turn into when you stop treating them as party tricks and string them into a single pass over a single real piece of work. The machine stops being the thing that lifts the weight for you. It becomes the weight.

Run this on anything that bears your name.

1. Write it badly, by hand. No machine. Whatever you’re making, the post, the proposal, the strategy. produce the worst possible first version yourself. The goal is not a usable draft. The goal is to find out what you actually think, which you cannot do until you’ve watched yourself try to say it.

2. Confess it. Paste that ugly draft into the machine and run The Confessor. Do not let it rewrite a word. Make it tell you what you’re really arguing and where you’re hedging. You are looking for the sentence you were circling but didn’t dare write.

3. Redraft by hand from what you found. Machine closed. Now that you know what you mean, write the real version yourself, built around the thing the Confessor dug up. This is the draft that has your fingerprints on it.

4. Put it in the ring. Run The Adversary on that draft. Let it hit every weak joint. Then answer every blow yourself, in writing, by hand, patching the argument, not asking the machine to patch it for you. Repeat until it stops landing clean shots.

5. Go abroad when you stall. The moment you feel yourself reaching for the obvious, the provincial, the thing everyone in your trade would say, run The Foreign Correspondent. Steal one frame from a field that isn’t yours, write down one book to read later, and come back. Use it to get unstuck, never to get finished.

6. Forbid the answer on the one hard call. then finish alone. There’s always a single decision at the heart of the thing you can’t quite make: the angle, the claim, the line you’re afraid to commit to. Run The Tutor Who Will Not Answer on exactly that one question and let it interrogate you until you decide. Then close the machine entirely and do the final edit in your own hand. You started it as yourself; you finish it as yourself. The machine only ever held the weight.

The whole pass costs you maybe an hour more than letting the machine do it. That hour is the work. And I’ll tell you, since I’ve been confessing all the way through: the days I skip the protocol and just prompt for the output are the days I can feel the muscle going slack again by evening.

The Part That Will Cost You Something

I will not pretend this is easy, because the difficulty is the same one I named on Tuesday, only sharper.

When you used the machine to scale, every incentive in your world applauded — quietly, mostly, the way people applaud a private vice that happens to be paying off. When you use it this way, to deliberately blunt your own velocity, you will get no applause at all, because no one will see it. Your output will, for a while, become slower and rougher and stranger. Your competitors will continue shipping their fluent nothing at twice your rate. The consultants will note, with that special pity they reserve for the obsolete, that you no longer scale. And you will have to want the slower, stranger, realer thing more than you want their approval, in private, where wanting things is hardest, because a good habit kept where no one can witness it is the loneliest discipline there is.

And since Tuesday’s letter was built on a confession, this one had better match it: I do not always manage it either. I issue the lazy prompt about as often as I issue the strategic one. The difference between a man recovering his mind and a man losing it is not talent, or virtue, or even awareness. It is mostly just which order he is in the habit of giving the machine at two in the afternoon, when he is tired, and the deadline is close, and the easy thing is sitting right there, glowing, asking only to be allowed to do his thinking for him.

If you are worried about how to come up with ideas and write and promote yourself after you stop using AI, then you are in the right place.

I used AI to find better ways to do those things than using AI, and then I created four courses:

The first is a FREE monthly masterclass about How To Never Run Out of Ideas Without Depending on AI. Grab a seat for the next one here.

The second is a masterclass about The Art of Making Clients Come To You

The third is an editing system I call The Copy Hunter Field Guide to Writing More Human in the Age of Age of AI. The first module is already up. (Use the code PRESALE to get it for $75 instead of $200)

The fourth is about Mastering the Art of Personal Publicity where I discuss the secret behind how Personal Brands are truly made. I’ll give you a hint. It has nothing to do with how you write, what you write about, or anything else AI can produce. Use the code RUBEN to get it for 50% off.

In addition to all that I also paid attention to how I use AI when I am not thinking about AI, and then turned it into one of my protocols for paid newsletter subscribers to train themselves with.

Subscribe now

The Heretic Protocol

The story goes that Count Basie was playing a club whose piano was, every single night, hideously out of tune. He finally told the manager he would not come back until the thing was fixed. A month later, word came that it was done, so Basie returned to find the piano exactly as sour as before. “I thought you said you fixed it,” he said. “I did,” said the manager. “I had it painted.”

People solve the wrong problem for two reasons.

The first is laziness: a problem is an unpleasant thing, and the lazy mind takes the first exit it can find, whether or not it leads anywhere.

The second is more flattering and therefore more dangerous because it involves a dominant skill, or a governing agenda, that quietly bends every problem toward the solution you already happen to own. You know, how to the man with a hammer, everything looks like a nail.

The automated man (like has been handed the most seductive hammer ever forged. He has become so good at AI that he can no longer see a problem that is not, to his eye, an AI problem. Ask him anything, and his hand is already moving toward the machine before the question has finished landing. He is like Professor Butts in the Rube Goldberg comics, so enchanted by automation that he will spend a feverish afternoon engineering a fourteen-step contraption to crack a single egg and feel, at the end of it, that he has done something ingenious rather than something absurd. He has made the simple tedious in the name of making it simpler, but he has done it because automation is the thing he knows how to do, not because automation was what the problem actually required.

The cure for this comes from physics: first-principles thinking. Which is not as mystical as Elon Musk and the consultants make it sound. Mostly it is just the refusal to accept the first solution that presents itself (and the first solution, for the Automated Man, is to have the machine do it) long enough to ask a few rude questions.

Am I solving the right problem, or merely the nearest one?

Is there a larger problem sitting behind this one that I am avoiding because it is harder?

Am I taking the first exit out of laziness?

Is there an agenda steering my hand, and if so, what solution is it quietly insisting on before I have even begun to think?

What is the simplest way to do this, if I pretend for a moment that my favorite tool does not exist?

Here is the irony, and you will either enjoy it or resent it:

The machine, precisely because it is a pattern-recognition engine and nothing else, is a superb instrument for this interrogation, provided you never let it answer in its own favor. Because asking your own AI whether you ought to rely on it less is very much like asking the priest whether you should stop coming to church. He will hear you out, kindly, and conclude that what you truly need is to come more often. Or, he will kindly tell you that maybe you should explore more before making a decision, but he says it in a way that the Amish say to their children before going off into the world for Rumspringa.

So, how do you use AI to determine whether or not you should use AI?

You do two things.

The first thing you do is use this prompt:

Read more

This newsletter is not addressed to , but if you follow him and are growing tired of your dependence on AI, it’s addressed to you.

I wrote it after featuring Ruben for a second time in my Anti Guru LinkedIn newsletter.

It is a manual for becoming worse at using artificial intelligence, which is to say, for becoming better at using the natural kind of intelligence.

I have no illusion that it will be welcome.

The efficiently automated Ruben Hassid crowd, like a happily drunk, do not wish to be disturbed or bothered. But then again, I have never written anything with the primary goal of being welcome, and I am too old to begin now.

This Is Not Another Anti-AI Newsletter

I want to be clear. I am not anti-AI.

This newsletter is not about why you shouldn’t use AI or why it’s evil.

This newsletter is for the person who has become too obsessed or dependent on it, and it assumes you have realized this overcommitment to AI and that you have been delegating too many of your mental faculties to a machine and that, after considering the alternatives, you have decided to limit your reliance on artificial intelligence.

Now, let us agree on just what this decision means.

It does not mean that you will throw the machine in the dustbin or unsubscribe from it in some spasm of neo-Luddite righteousness.

It means only that, from now on, the thinking, reasoning, forming of opinions, and writing of things that are either you or people facing and that bear your name (in short, the work that requires a mind rather than a processor) will be, for the most part, done by you.

In other words, you will continue to use the tool.

You will just cease to be used by it.

You will also probably consult the machine less frequently. Certainly, you will accept its outputs less reflexively. You may even discontinue certain habits you have come to dislike, both in receiving and in sending. Things like the automatic generation of emails you could have written yourself, the summarization of articles you should have read, the drafting of proposals whose premises you have never examined. In short, you will go right on earning your keep conscientiously, but you will no longer be “scalable” (as the consultants will put it when they remark the change in you).

You may have arrived at this decision for many reasons, but behind them all there must have loomed either a growing distaste for what your work has become or an interest in recovering something you have lost.

You need not have been as bitter as a former creative director I know who described his recent output with the most self-castigating statement of its kind I have ever heard:

“I have become a very expensive middleman between a client’s brief and a machine’s response. I add less value than a semicolon.”

In your case, it may only have been that you noticed your writing no longer sounded like you, or that you reached for a thought only to find an echo chamber.

The reasons for withdrawing reliance on AI are as numerous as the people who do it.

But don’t underestimate the difficulty of bringing about such a change.

Why Making This Decision Is Harder Than You Think

It’s quite a feat to diminish a solidly established dependency.

The decision to stop outsourcing your thinking or doing is not any more significant than any other resolution to give up a habit that mo longer or never worked for you:

The problem with this particular habit, however, is that using AI to do your work is a custom that is universally applauded. And that while some people universally applaud it in public, most do so in private. And it is always harder to break a good habit than a bad one. But it is even harder to break a private good habit than a bad one. Because when someone like Ruben Hassid smiles on something you have been doing, or when every conference speaker and management consultant and LinkedIn guru is urging you to do more of it, or when your employer has invested considerable sums in the tools that make it possible, and even made it mandatory and when your colleagues and competitors will almost unanimously think less of you for ceasing to do it (or, worse, will quietly surpass you) the odds of you being able to abandon the habit shrink considerably.

But when the joy and feelings of success using AI are private, that is, when no one knows you’ve been using AI because it’s working, that is a much harder thing to give up. It is not like giving up nail-biting or excessive drinking. There, everyone is behind you in your decision, even if they don’t know you're making it. It is more like trying to give up praying at church. You are not just flouting convention. You are flouting your own convention. And by your act of abnegation, you are challenging the avowed secret convictions of individual desires and the metrics by which it measures its worth.

And so a great gap yawns between your decision to reclaim your mental labor and the moment when you can truthfully say that you have reclaimed yourself.

Making the decision to do it is the first step.

But a decision is merely a prelude.

The so the only way a habitually automated professional can stop outsourcing his mind to AI is not just to stop wanting the effortless output, but also to want something larger. You must also want to stop scaling at the speed of everyone else. And there lies another challenge because if you work in marketing or business of any kind, you’ve grown accustomed to the concept of scaling. After all, if you are not scaling, then what are you doing? Surviving? And to stop wanting something you’ve grown accustomed to is quite an act of will.

There are, nevertheless, several ways a person can approach the task of wanting to be less good at AI. All of them are techniques of self-manipulation, and their effectiveness varies from person to person.

Before we can discuss how to be worse at outsourcing yourself to AI, we must, of course, understand what the outsourced person looks like, and here we encounter a difficulty unique to this particular affliction because most diseases announce themselves.

The Automated Mind: A Clinical Portrait

The man with a broken leg knows his leg is broken.

The man with a fever feels hot.

But the man who has stopped thinking feels nothing at all, or rather, he feels more productive, which in our civilization amounts to the same thing.

I have been observing this creature within myself, as well as in Ruben, over the past 3 years and have identified the following characteristics about such a man.

He can produce, but he cannot originate. He is prolific in the way that a photocopier is prolific; he generates an enormous volume of material, all of it competent, but none of it is really his. Ask him for a marketing strategy, and he will give you one within fifteen minutes. It will be coherent, well-organized, and supported by plausible reasoning. It will also be identical, in its essential character, to the strategy that anyone else using the same machine would have received, only the fingerprints have been wiped clean, and what remains is a document that could have been written by anyone, which is another way of saying it was written by no one.

He has confused velocity with thought. The automated mind measures its output in speed. It’s not just that he can produce a report in twenty minutes that used to take two days. It’s that he experiences this acceleration as progress. But consider: a two-day report was a two-day report, not because the typing took two days. It took two days because the thinking took two days. The pauses, the false starts, the crumpled sheets in the wastebasket, the long stare out the window, the walk around the block that produced, halfway down the second street, the idea that unlocked the whole thing, these were not inefficiencies to be automated. They were the work. The machine has not eliminated the inefficiency. It has eliminated the work and kept the appearance of it.

He reads summaries of things he should be reading. This is perhaps the symptom that distresses me most, because I have spent a lifetime arguing that reading, real reading, immersive reading, the kind of reading where you dip yourself into a book like a shrimp into cocktail sauce and come out changed, is the foundation of any mind worth having. The automated man does not read. He has his machine read for him, and either produces a summary which he then skims, or worse, the work itself, which he posts or shares. Which means he has achieved the remarkable feat of being secondhand about a secondhand experience. And is twice removed from the original thought, and what is sad is that he does not know it, because the summary or finished work is competent, and competence, as I have said, is the ceiling of his ambition.

He has no voice. I mean this literally. Read his emails, his proposals, his social media posts; they are all written in the same voice. Not his voice (when he was writing about ghostwriting 4 years ago, he had a voice). Now his writing is just a voice. A pleasant, professional, slightly warm, slightly clever voice that belongs to nobody and everybody. All written in a tone and style that is the verbal equivalent of hotel art, which is to say that it is inoffensive, adequate, and impossible to remember. His audience, if asked, could probably not distinguish his writing from anyone else’s, because it is not his writing. It is the machine’s writing, and the machine writes for everyone in the same accommodating, characterless tone, like a Hooters waitress that has been trained to seem friendly without actually being a person. But none of this matters to him because it’s making him more efficient and it’s working.

He is succeeding. And this is the cruelest symptom of all, because it is the one that makes the condition invisible and impossible to get over. If the man who outsourced his thinking were failing, if his work were poor, if his clients were unhappy, if his career were suffering, he would have cause to examine his methods. But he is not failing. He is, by the standards his world applies, thriving. As a matter of fact, his output has increased. His efficiency is unquestioned. The machine has made him a more effective professional, and it has accomplished this by the simple expedient of replacing him entirely while leaving his body in the chair. This is made even worse if the subject matter he is discussing is about automating yourself itself.

If you recognize yourself in this portrait (and I suspect some of you do, though the recognition may arrive with a delay, and you want to stop recognizing yourself in this portrait, then what follows is for you.

Why Success Is The Problem

I must address, before going further, the objection that is already forming in the mind of every efficient person like Ruben reading this. And I can almost guarantee that Ruben will not actually read this. He will probably have his AI read it and ask it how to respond. But if he did read this, his argument would probably go something like this:

“If it’s working, what’s the problem?”

And it is a good argument because it is a fair question.

But it is also the wrong question.

Because the problem is not that the machine is failing you. The problem is that it is succeeding, and its success is making your failure invisible. You are not failing at your job. You are failing at being a mind, and nobody has noticed, least of all you, because the job continues to get done.

Let me put this differently:

Much of marketing is based on something called the Promotion Instinct. The promotion instinct is the deep human drive to present oneself favorably and gain the consent of other men. This instinct is ancient and powerful, and it explains nearly all of human behavior not explained by hunger or lust.

And the automated man has found in his machine the most powerful instrument of the Promotion Instinct ever devised, because it makes him look smarter, faster, more articulate, and more knowledgeable than he actually is. But it is, in a McLuhan sense, a prosthetic personality, and like all prosthetics, it works beautifully until the moment you need the real limb and discover it has atrophied.

When does that moment come?

It comes in the conversation you did not expect.

It comes in the meeting where someone asks a question that is not in the brief, and you must answer from your own mind, and you reach for a thought and find, where a thought should be, only the smooth blankness of a machine-polished surface.

It comes at three in the morning when you wake up and try to think about your life and discover that you cannot, because thinking is a muscle you have not used in months, and it has gone slack. It comes when, instead of trying to solve a problem, you think of ways to train an AI to solve it for you.

It comes, most devastatingly, in the gradual and almost imperceptible erosion of your judgment. Because judgment is not a faculty that can be maintained in storage. It must be exercised. It must be used daily, on real problems, with real stakes. And the man who delegates his judgment to a machine does not preserve his judgment for when he needs it. He loses it. Slowly and invisibly, but also completely.

I have always had a slight distaste for the company of my fellow men, and this has thrust me into the bosom of writing long newsletters like this. But if there is anything the age of AI has helped me realize, it is this:

I would rather spend an evening with the most tediously annoying man alive than with the most brilliant machine, because the tedious man, at least, is there. He is present. His tedium is his own. The machine’s brilliance belongs to nobody.

Why You Should Want To Be Worse At Using AI

Now, if you happen to be reading this not because you have decided you need to become worse at using AI but because you find the idea appealing, you probably have a question. And that question is probably something like:

Why should you want to be worse at outsourcing my mind?

Let me count the reasons, and let me begin with the most important one, which will sound, to the efficiently automated, like the ravings of a man who has failed to keep up with the times and is doomed to obsolescence, but which must be said anyway.

Because I am not the one disappearing, you are disappearing. I mean this with a precision that I hope will alarm you. The thing that makes you you, the particular way you see the world, the specific texture of your thought, the cadence of your sentences, the idiosyncratic connections your mind makes between apparently unrelated things, that thing is dying the way an ancient language dies: through disuse. Every time you ask a machine to write something you could have written yourself, you are choosing not to exercise the faculty that makes you a distinct human being. Every time you ask it to think something you could have thought yourself, you are allowing the mental equivalent of a muscle to atrophy. And the tragedy is not that the machine does it badly. The tragedy is that the machine does it well enough that nobody cares.

Because competence is not intelligence. The machine produces competent work. But it does not produce intelligent work. This distinction, which would have been obvious to any educated person fifty years ago, has been obscured by our culture’s catastrophic confusion of output with quality. Competent work meets the specification. Intelligent work transcends the specification. Competent work answers the question that was asked. Intelligent work asks the question that should have been asked. The machine is incapable of the latter, because the latter requires the thing the machine does not have and cannot simulate, which is a point of view. Simply speaking, the machine has no point of view. All it has is a statistical average of everyone’s point of view, which, once again, is another way of saying it has no point of view at all.

Because it is making you provincial. I have argued all my life against provincialism, against the narrowing of the mind that comes from knowing only one thing, reading only one kind of book, associating only with one kind of person. People who are under-read tend to be under-generalized, and the under-generalized man is a case of arrested development. The man who outsources his thinking to a machine is the most provincial creature I have ever encountered, because even though it does not feel like it to him, he has narrowed his intellectual life to a single source. He does not read books; the machine reads them for him. He does not grapple with ideas; the machine grapples with them and presents him with the results. In other words, he lives in a province of one, bounded on all sides by the machine’s outputs, which he mistakes for the world.

Because you cannot sell what you do not understand. I am, lest we forget, a man who has spent his life in the business of persuasion. And I will tell you something that no amount of artificial intelligence can change: you cannot persuade someone of something you do not yourself understand. You cannot write an advertisement for a product you have not thought about. You cannot craft a strategy for a market you have not immersed yourself in. The machine can produce the words. And it can produce it at a scale where eventually you may produce Shakespeare. But it cannot produce the understanding behind the words. And the consumer who is, whatever our industry’s pretensions, a human being with a human being’s instinct for authenticity, can tell the difference. He may not be able to articulate the difference. But he feels it the way you feel, in a conversation, the difference between a person who is present and a person who is reciting.

Because the machine cannot be wrong in interesting ways. This is perhaps the most subtle loss, and the one that will matter most in the long run. Every interesting idea in the history of advertising, every campaign that surprised, every slogan that entered the language, every piece of work that made people stop and think, began, I would argue, as a mistake. Or as a wrong answer. Or as an idea that, by any reasonable standard, should not have worked. But it did work. Because the human mind, unlike a machine, is capable of being wrong in ways that are more interesting than being right. AI is never interestingly wrong unless we perceive it to be (more on that later). It is always competently right (even when it’s wrong). And competently right, over time, is the most boring thing in the world.

Because the appearance of truth is more important than the truth. And by this I do not mean lying. What I mean is that truth is important. But if something that is true doesn't appear true, then no one will care or notice or think it’s true. There is a word for this,m the appearance of truth. I have talked about it before. Verisimilitude. It is probably one of the most underrated words in marketing and human relations in general. Millions of great and true ideas are probably overlooked because they do not appear to be true. Anyway, my point in bringing this up is that AI has, whether we like it or not, a verisimilitude problem. Simply put, what you put out or say to the world may be true, accurate, and life-changing, but the minute people sense that you use AI to say it or post it, the appearance of truth is gone.

Having established why you should want to be worse at this, let us proceed to the practical business of how.

How to Stop Wanting To Be Good At AI.

What follows are six techniques for recovering your mind from the machine that has borrowed it. They are simple to understand and difficult to practice, which is true of everything worth doing and also of several things that are not.

TECHNIQUE 1: THE DISCIPLINE OF THE FIRST DRAFT

The first technique is designed to ease you off of AI slowly. It doesn’t require you to not use AI. It just requires you to do it yourself before you ask the machine.

So, for example, before asking the machine to write anything, write it yourself first. But do not try to write a good version. Write a bad version. A terrible version, if that is what comes out. Then use the time you would have spent writing a prompt to write the email yourself before asking the machine to write it. Draft the proposal yourself before generating one. Compose the post yourself before having it composed for you.

The purpose here is not to produce something usable. The purpose is to think. And exercise the muscle that does the thinking. Because writing, real writing, is not a method of recording thought. It is a method of producing thought. And you do not know what you really think until you have written it down because the act of writing forces you to confront the vagueness of your own ideas, to discover what you actually believe as opposed to what you assume you believe, to find the gaps in your reasoning and the contradictions in your position.

AI eliminates this process entirely. When you ask the machine to write for you, you skip the part where you discover what you think. You go directly from the vague intention to the polished output, and the polished output looks so much like thought that you mistake it for your own. But it is not your own. It is a statistical composite of what millions of other people have thought about similar subjects, averaged into a smooth paste and flavored with your name.

So write first. Write badly. Then, if you must, ask the machine and use what it gives you. But write first. The discipline is in the sequence.

If you want to take this a step further, don’t ask AI to polish or edit your work or its work. Do the editing yourself. This is important because writing, real writing, is 75% editing anyway. If you are interested in this, I created a course on Editing AI content (or any content) to sound more human, better, or whatever. It's called The Copy Hunter Field Guide for Writing Like A Human in the Age of AI. It consists of 52 things to hunt for and change in any long-form writing to make it sound more human or more professional. The first module of 10 hunts is being released now. Use the code PRESALE to get it for $75 instead of the $200 it will be when it is complete.

TECHNIQUE TWO: THE REINTRODUCTION OF FRICTION

This technique is all about deliberately making things harder for yourself.

The entire promise of the machine is the elimination of friction, the removal of difficulty and the smoothing of the path between intention and result. This has been presented to teh world as an unambiguous good. But it is, in fact, an ambiguous disaster because friction is where learning happens. Friction is where understanding lives. The difficulty of writing a sentence teaches you something about language that no amount of reading generated sentences can teach. The struggle to organize your thoughts teaches you something about your thoughts that no summary can convey. The frustration of not being able to articulate what you mean is not a problem to be solved by the machine; it is the process by which you discover what you mean.

In my free monthly masterclasses about how to never run out of ideas to post about without relying on AI, I talk extensively about the importance of reading for immersion and of dipping yourself into a book like a shrimp into cocktail sauce and coming out changed. The metaphor applies here too. Thinking is an immersive activity. It requires time, effort, discomfort, and the willingness to sit with confusion until confusion clarifies itself into understanding. The machine offers you a shortcut past all of this. The shortcut is real. What you lose by taking it is also real, and far more valuable than the time you save.

Here’s an exercise you can apply right now: choose one task each day that you would normally delegate to the machine, and do it yourself. Do it the hard way. Do it slowly. Accept that the result will be less polished, less efficient, less “professional” than what the machine would have produced. Then look at what you produced and notice something: it is yours. It has your fingerprints on it. It sounds like you. It may not be as smooth as the machine’s output, but it is real in a way that the machine’s output is not, and that reality is worth more than all the polish in the world.

TECHNIQUE THREE: THE PRACTICE OF UNASSISTED READING

The third technique is the one closest to my heart, because it concerns the activity I have loved longest and most fiercely and once again I talk about extensively in my free Masterclass on how to never run out of ideas without relying on AI

As I said before, I have always believed that reading is the foundation of a mind worth having. Men who are under-read tend to be under-generalized, and the under-generalized man is a case of arrested development. This was true when the chief threat to reading was the television set. It is catastrophically truer now that the chief threat to reading is a machine that will read for you and tell you what the book said.

Because the machine’s summary is not reading. Let me be absolutely clear about this. The machine’s summary is to reading what a postcard of the Mona Lisa is to the Mona Lisa. It conveys the rough shape of the thing, and nothing else. Reading, despite what Ruben might say, is not the extraction of information from a text. Reading is the immersion of a mind in a mind. It is the encounter between your way of thinking and someone else’s way of thinking, conducted at the speed of thought, with all the digressions and confusions and surprises that such an encounter entails.

When I read Henry James or Thomas Mann, or J.K Rowling, I am not acquiring information about what Henry James or Thomas Mann or J.K Rowling thought. I am submitting myself to the experience of thinking alongside them, following their sentences, feeling their rhythms, inhabiting their assumptions, being led through corridors of thought I would never have entered on my own. But I am also becoming the author myself because I am reading their words from my perspective of the world. Not theirs. This is what I meant by immersion reading. It is also what I mean when I compare it to you being a shrimp and the book is a cup of cocktail sauce. You dip yourself in, and you come out changed.

But a summary does not change you. A summary informs you, superficially, provisionally, and forgettably. The man who reads summaries instead of books is the man who eats the menu instead of the meal and congratulates himself on his efficiency.

So, from now on, read one book a month, watch one YouTube video a week, or read one long article a week, with no mechanical assistance whatsoever. No summaries, no key points extracted, no AI-generated reading guides. Just you and the words, alone together, the way it has been done for five centuries. Mark it up. Argue with the author in the margins or comments. Get lost. Get confused. Get bored, then push through the boredom and come out at the other end with something you did not start with. That something is called understanding, and there is no shortcut to it.

TECHNIQUE FOUR: THE CULTIVATION OF SILENCE

The fourth technique involves the deliberate practice of having nothing to say.

The machine has made it possible to have something to say about everything. A question arises, about a market, a strategy, a competitor, a trend, and within seconds the machine can furnish you with an intelligent-sounding response. The result is that the automated man never has to admit ignorance. He is never without an opinion. He is never caught, as the rest of us occasionally are, with his mouth open and his mind empty.

This sounds like an advantage. It is not. Because the capacity to have nothing to say, that is to encounter a question and genuinely not know the answer, is one of the most valuable capacities a mind can possess because it is the beginning of a wonderful thing called curiosity, which is the precondition for learning. Which is, in a profession that depends on understanding people you have never met and markets you have never experienced, absolutely essential.

The man who always has an answer never learns anything, because learning begins with the recognition that you do not know. AI has abolished this recognition. Worse than that, it has given you an answer to every question before you have had time to discover that you did not have one, and in doing so, it has deprived you of the experience of not knowing, which is the experience from which all genuine knowledge grows. And worse than that, it has given you the ability to spray this information across the world and call it your own.

So from now on you need to let yourself not know. When a question arises in a meeting, resist the urge to consult AI. Sit with the question. Say, “I don’t know. Let me think about that.” Then actually think about it. Try to answer the question yourself with whatever information you have. The pause between the question and the answer is where your mind lives. Do not fill it with AI’s voice. Fill it with your own silence, and wait for your own thoughts to arrive. They will come more slowly than the AI. They will be less polished. But they will come. And, more importantly, they will be yours.

TECHNIQUE FIVE: THE RECOVERY OF BOREDOM

The fifth technique is related to the fourth in the way that a root is related to a branch because boredom, like silence, has been nearly eradicated by AI. The automated man is never bored. When his attention flags, in a meeting, on a commute, in the dead hours of the afternoon, AI is there to stimulate him, to create dopamine hits every time it generates content and fill the empty moments with activity that feels like thinking but is not.

But boredom is, and never has been, the absence of stimulation. It is, in fact, the opposite. Boredom is the mind’s way of telling you that it needs to do its own work. It is the signal that the subconscious processes, the ones that produce genuine insight, original connection, creative breakthrough, require time and emptiness in which to operate. The mind, like a field, must sometimes lie fallow. AI never lets it lie fallow because AI keeps planting, every hour of every day, and the soil is exhausted, and the crops are getting thinner, and the automated man does not notice because the machine keeps presenting him with the same impressive yields, regardless of what is actually growing.

I recommended in an earlier newsletter the strategic cultivation of boredom, and I recommend it again here with particular urgency. Set aside time, fifteen minutes, half an hour, in which you use no machine at all. Not to be productive. Not to think great thoughts. Just to be bored. To let the mind wander where it will, without direction, without purpose, without the machine’s helpful suggestions for what you might think about next.

You will be surprised by what surfaces. Or you will not be surprised, because nothing will surface, and that is also instructive. Either way, the emptiness will tell you something about the state of your mind that the machine’s constant activity has been concealing. Listen to it.

TECHNIQUE SIX: THE MAINTENANCE OF A PRIVATE MIND

The sixth and final technique is in some ways the most radical suggestion I have to make, and I make it with the full expectation that it will be dismissed as impractical, sentimental, or both.

I tried to explain once, in a podcast interview, that we are not one person but several and that when I try to make a living, I am one man, and when I think about the human race, I am another, and when I think about myself, I am another still. The interviewer was polite enough not to look at me as if I were mad or bored or confused, but I could tell he was not entirely persuaded.

I also talk about it in my Mastering the Art of Personal Publicity course (use the code RUBEN to get 50% off), hopefully in a more persuasive way.

The point I was making then applies with even greater force now. We have professional selves and private selves, public minds and inner minds. The professional self may, perhaps, be allowed to use AI, to draft and polish and summarize and produce. But the private self, the inner mind, must be kept free of it. There must be a part of your mental life that the machine never touches.

I mean this with a specificity that may seem eccentric. I mean: do not use the machine to compose personal letters. Do not use it to help you think about your relationships. Do not use it to generate journal entries, process your emotions, write love letters or birthday cards, or decide what you believe about matters of genuine importance to you. These are the activities of the inner mind, and they must be done in your own voice, at your own speed, with your own confusion, or they are not being done at all.

I think it goes without saying that the man who uses AI to write a love letter has not written one. He has ordered one from a catalog, which is not the same thing (ladies, tell me if you disagree). Similarly, the man who uses the machine to organize his thoughts about his life has not organized his thoughts about his life; he has had thoughts organized for him, which I believe most therapists would agree is a fundamentally different experience, the way being carried somewhere is a fundamentally different experience from walking there yourself.

So from now on, keep a part of your mind that is yours alone. Write in it. Think in it. Be confused in it. Be wrong in it. Because that part does not need to be efficient or productive or produce outputs. It is not a factory. It is a mind. It is your mind, and its value lies not in what it produces but in the fact that it is there, and that it is yours, and that it is working, however haltingly, under its own power.

The Deeper Problem

I have offered six techniques for recovering your mind from AI, and I believe they are useful. But I have learned, over a long career of diagnosing ailments and prescribing remedies, that the symptom is never the disease and that the disease is always deeper, and always less comfortable to examine, and always more interesting.

And the deeper problem here is not laziness. The automated man is lazy. Ironically, he works very hard; he just works hard at the wrong things. He works hard at managing the machine, at crafting prompts, at evaluating outputs, at the meta-labor of producing without producing. He is, in his way, as industrious as anyone I have ever met. His industry is simply misdirected.

No. The deeper problem is cowardice.

I use the word deliberately, knowing it will sting, but not caring much if it does, because I have never found that the truth improves when you sand down its edges.

Simply put:

The man who outsources his thinking to a machine is, at bottom, a man who is afraid of his own mind.

Why?

Because he is afraid of what he will find there. He is afraid that his ideas, if he actually has any, will be mediocre. He is afraid that his writing, if he actually writes it himself, will be clumsy. He is afraid that his thinking, if he actually does it himself, will be slow and muddled and full of gaps. He is afraid, in short, that without the machine he will be revealed as what he secretly suspects he is: ordinary.

And so the machine serves not only as a tool but as a shield, a shield against the terrifying encounter with one’s own limitations. And AI’s outputs are never ordinary. They are always competent, always adequate, always just good enough to spare their user the knowledge of what he would have produced on his own.

But here is the thing about ordinariness that the automated man has either never discovered for himself or been put in a pressure-tested situation to realize himself:

Ordinariness is where everything good begins.

Every writer who ever wrote anything worth reading began by writing badly. Every thinker who ever had an original thought began by having obvious ones. Every advertiser who ever produced a campaign that moved people began by producing campaigns that moved no one. The ordinary self is not the enemy of the excellent self. It is the ground from which the excellent self grows. And the man who uses the machine to skip past his own ordinariness is a man who has cut himself off from the only soil in which genuine excellence can take root.

One of my main reasons I got into marketing and advertising and for doing what I do is to avoid being bored to death. I am also, though I said it less often, trying to avoid being dishonest with myself. But the AI makes self-honesty very difficul because it is hard to know what you really think when the machine is always there to tell you what you should think and it is hard to know what you can really do when the machine is always there to do it for you and it is hard to know who you really are when the machine is always there to be a better version of you.

Let me suggest that the worst version, your version, the slow, clumsy, and ordinary on, is worth more than all the machine’s polished surfaces. Not because it is better. It is probably not better. But because it is real, and reality, however awkward, is not only the only material from which a life can be built. It is also, whether they want to admit it or not, the only part of you that people really want.

A Concluding Note

I know what certain readers like Ruben are thinking, because I read them in Ruben’s posts and have been hearing the objection in my head since I began writing this, and it has been growing louder with every paragraph.

“Justin, you are a dinosaur. You are a Luddite. You are a man who is driving into the future while looking into the rear-view mirror. AI is here. It is not going away. The people who use it will prosper. The people who refuse to use it will be left behind. Your newsletter is a monument to irrelevance.”

To wish I say…

Perhaps.

I have been wrong before. But, unlike Ruben and the Automated Ma, I have never found the experience unbearable. In fact, I have always admitted to my inability to wrap my mind around abstract questions with any degree of finality. I mumble and growl and try to find the answers. But the truth is, when there are no answers, only the hypocrites will give you the answers.

But let me offer this, if not as an answer, then as an observation from a man who has watched the business of persuasion for a very long time and has seen several revolutions come and go:

Every revolution in communication has produced two kinds of people:

1. Those who used the new tool to amplify what they already were, and

2. Those who let the new tool replace what they might have been.

AI is a tool. It is perhaps the most powerful tool for manipulating language that has ever been devised. It can make you faster, more productive, more polished, more prolific. It can do everything for you except the one thing that matters:

It cannot be you.

Ruben Hassid is not a bad man.

He is not a stupid man.

But he is a man who found a very efficient way to stop being himself, and teach people how not to be themselves, and who has not yet noticed the loss.

My hope for him, and for you, is that you notice it before it becomes permanent, before the muscle has atrophied beyond recovery, and before the shrimp has forgotten what cocktail sauce tastes like because he has been eating the label instead of dipping himself in.

And, as Marshal McLuhan pointed out.

You do not look into the review mirror to see what you passed.

You look in the rearview mirror to see what is coming.

And as a student of advertising and marketing history (and history in general), I have looked in the rearview mirror, and I do like what I see, but I do not hate it either.

Because there was a time, it seems very long ago now, but it is not, when the mind did its own work.

But that time is not gone. It is only sleeping.

And I believe, as I have always believed, that in the end it may well be thinking, real, slow, difficult thinking, your thinking, that will make men free.

If you are interested in how you can use AI Against Itself to become worse at AI, read the second edition of this newsletter: The Uses of Artifical Stupidy Part II

- Justin Oberman

Last week OpenAI launched Codex.

Codex learns your workflow. It studies how you work, your patterns, your preferences, your process, and becomes increasingly good at anticipating what you need before you ask for it.

For most professional tasks like logistics, coding, scheduling, and a hundred other repetitive decisions that eat time without producing anything genuinely new this week a tool that learns your workflow and removes friction is useful.

But there is a category of work where learning and repeating your workflow is not an advantage.

And that category is creative work.

And the reason most people will not notice this distinction and will enthusiastically adopt Codex for their creative process the same way they adopted every other AI tool, is because most people do not actually know what the or their creative process is.

And that’s because the creative process is not an optimized workflow.

It is the deliberate disruption of one.

Most people, if asked to describe their creative process, will describe a production process.

They sit down. They open their tools. They generate material. They refine it. They ship it.

Or they study something intensely, write down a few ideas, and then do something commonly called “incubating” and somehow during that incubation process ideas suddenly emerge.

But what is being described there is not really a process. It’s more of a manufacturing process with creative-sounding inputs.

A genuine creative process has one defining characteristic that manufacturing processes do not.Abby.

What The Creative Process Actually Is

Every genuinely new idea in the history of human creativity came from someone who was paying attention to something that had nothing to do with the problem they were trying to solve.

John von Neumann was not at a poker table thinking about economics. He was at a poker table thinking about poker. The connection happened because he was somewhere unexpected and his mind, trained on a different problem, recognized a pattern that the economists who stayed in their offices never could.

Charles Eames was not designing chairs when he made plywood splints for wounded airmen. He was solving a medical problem. The chair came later, when the solution to one problem became the raw material for another.

Knute Rockne was not at a burlesque show thinking about football. He was at a burlesque show watching dancers. The backfield shift came from a chorus line because a football coach was somewhere a football coach was not supposed to be.

In other words, new ideas do not come from looking harder at what you already know. They come from looking elsewhere, from the productive collision between a problem you are carrying and an idea you found somewhere it had no business being.

Why AI Cannot Do This

Codex learns your workflow.

Your workflow is the path you already take. that involve the tools you already use and the sequence you already follow.

And AI is very good at doing this because that is what AI was built to do.

It is a pattern recognition and prediction machine.

So all it is doing is picking up on the patterns you have already established through repetition.

A tool that learns your workflow and optimizes it is a tool that makes you better at going where you already go.

But that is exactly the opposite of what the creative process requires.

Because the creative process requires going somewhere you have never gone and finding the connection between that place and the place you are usually at in way that does not exist yet.

If you ask AI to make the sleep, it will do so by trying to create a pattern out of it. But patterns are exactly the thing that creativity breaks.

AI cannot make that break because AI is a pattern recognition system.

It finds patterns in what already exists and optimizes for what has already worked. It learns what you do and gets better at helping you do more of it.

What it cannot do bevause l it is architecturally incapable of doing it is generate the genuine randomness of the productive accident and unexpected collision of two things that had no reason to be in the same room. We’re in the case of the AI, screen..

The Prospector’s Problem

If you look in the same old places, you will find tapped out veins.

Miners who find gold are rarely the ones who dig deeper into the mines everyone else is digging in. Miners who find gold are usually the ones who go somewhere nobody had thought to look, who followed a hunch, took a wrong turn, and ventured off the path that the more efficient miners had long since optimized.

This is because efficiency, in prospecting, is a trap.

The efficient miner works the known veins harder.

The creative miner goes looking for new ones.

Thomas Edison understood this so well that he gave his lab colleagues explicit instruction:

“Make it a practice to keep on the lookout for novel and interesting ideas that others have used successfully. Your idea has to be original only in its adaptation to the problem you are currently working on.”

Not original in its source.

Original in its application.

The idea can come from anywhere. The creativity is in not in the collision. It’s in recognizing that something from over there solves a problem over here.

But you cannot make the collision or recognition if you never go over there.

A tool that learns your workflow will make over here more efficient. It will optimize the path you already take. It will remove friction from the process you already follow. But it will never take you over there.

The Setup

The protocol prompt for paid subscribers this week is a structured cross-domain idea hunting system.

This is not the same thing as a brainstorming technique.

Nor is this a creativity prompt. It is a way to use AI in way that creates a deliberate friction that forces you to go somewhere your workflow and AIs workflow does not and will not take you, and helps you bring back what you find so that you start making collisions.

And if you ask me it teaches you how to use AI in the only way I think AI is genuinely useful for creativity: not to generate ideas, but to help you follow connections once you have found the raw material yourself.

The Prospector’s Protocol: A System For Finding Ideas Where Nobody Else Is Looking

This protocol comes in two parts.

Part 1 is the practice itself: what you do, how you do it, how often.

Part 2 is how AI enters after the prospecting is done.

PART 1: THE PROSPECTING PRACTICE

The core move here is to create a deliberate domain displacement.

Read more

Social media platforms were designed to be social, interactive, conversational, two-way communication tools. That’s why people initially join them.

But successful personal brands don’t use these platforms the way average users do.

And this creates a fundamental tension.

Think about the dynamics of a dinner party:

The Dinner Party Principle

Everyone’s there to socialize. To interact. To have meaningful exchanges.

But watch what happens when someone with presence—real presence—enters the room.

They don’t attempt equal one-on-one conversations with every person. Yet somehow, by the end of the night, everyone feels like they had a meaningful interaction with them.

This is the exact model you need to adopt as your brand grows.

Politicians, celebrities and successful executives don;t just master this. They embody it. Anyone who’s taken a Dale Carnegie course practices this.

They’ve learned to create the feeling of personal connection through selective attention, a gesture, a look, a nod, a brief acknowledgment that feels genuine but requires minimal time investment.

The Evolution of Your Social Strategy

Your approach to social media needs to evolve through distinct phases:

Phase 1: True Two-Way Communication

• When you’re starting, use platforms exactly as they were designed

• Respond to every comment, accept every connection, answer every DM

• Build relationships one person at a time

• This works when you have dozens of engagements, not hundreds

Phase 2: Selective Authentic Engagement

• As your audience grows, shift to quality over quantity

• Make your engagement feel personal even when it can’t be comprehensive

• Use small gestures (likes, brief acknowledgments) strategically

• Reserve deep engagement for those who truly warrant it

Phase 3: Systemized Connection at Scale

• With significant audience size, implement systems for authentic-feeling engagement

• Create the illusion of personal attention without sacrificing your creative energy

• Develop frameworks for quick decisions about who deserves your focused attention

• Leverage technology to extend your personal touch

The goal isn’t to become less social—it’s to become more strategic about how you express your sociability.

My Practical System for Managing Growth

After years of experimenting, here’s what works for me:

Comment Strategy: Giving and Receiving

First, let’s start with your Outbound Commenting (Your Comments on Others’ Posts)

This is the most overlooked growth strategy. I spend 10-15 minutes daily scrolling my feed and leaving thoughtful comments for three specific reasons:

1. Algorithm Enhancement: Platforms reward active users who create conversations

2. Content Research: If your comment gets significant engagement, it’s a sign you should develop that idea into a full post

3. Mini-Content Opportunities: LinkedIn gives you ~1,000 characters in comments—enough to showcase your thinking without the pressure of a full post

Don’t force this. Comment only when you have something valuable to add. Quality over quantity always wins.

Now let’s discuss inbound commenting (Managing Comments on Your Posts)

For posts with moderate engagement:

• I like every comment that comes in within the first 1-3 days

• I actually hang out on the platform after posting to respond in real-time

• This boosts algorithmic reach and lets me engage while my thinking is fresh

For viral posts with overwhelming comment volume:

• I abandon any pretense of strategy and simply follow my intuition

• I respond to comments that either:

  1. Touch a nerve (positive or negative)

  2. Add substantial value to the conversation

  3. Come from people I genuinely respect or want to connect with

Yesterday, someone I deeply admire commented on my post. My response was simply: “Of all the comments I’ve received today, hearing this praise from you meant the most.”

Pro Tip: Don’t just engage with potential clients. Build relationships with fellow creators and influencers in your space. These peer connections often lead to the most valuable opportunities.

The 5% Rule

After years of experimenting with different strategies, I’ve developed what I call the 5% Rule:

Invest 10% of your energy in creating valuable content and 90% in talking to people. And of that 90%, focus on the top 5% of interactions that matter most.

Let me break down what this looks like in practice:

For Comments:

1. The great thing about comments on your post is that you’re already on your posts, so you don’t have to worry about reach. Therefore, when commenting, you don’t have to worry about the person you're commenting on. But instead, you should worry about the comment itself. Identify value-adding commenters (not based on who they are but by what they say)

   • Who asked thoughtful questions?

   • Who provided additional insight?

   • Who has an audience you want to connect with?

   • Who might become a client/customer?

2. Respond meaningfully to these select few

   • Write thoughtful, value-adding responses

   • Ask follow-up questions

   • Tag them by name

3. For all others:

   • Like their comment (acknowledgment without time investment)

   • Occasionally leave a simple emoji or “Thanks!” on random comments (keeps engagement algorithms happy)

   • Ignore the rest entirely (yes, really)

Handling Shares

When people share your content, they’re amplifying your message without asking for anything in return. These people deserve acknowledgment.

Two types of shares require different approaches:

1. Simple Shares: When someone shares without adding commentary, a simple like is sufficient

2. Value-Adding Shares: When someone shares with their own insights, I like the share and leave a comment

At minimum, I comment “Thanks for sharing!” But if they’ve added meaningful perspective, I’ll engage with their thoughts directly.

This closes the loop and encourages more people to share your content in the future.

Connection Requests: Quality Over Quantity

I used to be what I call a “connection junkie” accepting every request that came my way. Now I’m more discerning for several reasons:

1. Algorithm Considerations: Your feed quality is determined by your connections

2. Platform Limits: LinkedIn caps you at 30,000 first-degree connections

3. Signal-to-Noise Ratio: Meaningful opportunities get buried in volume

My current approach:

• I look for personalized connection notes (auto-accept these if they’re genuine)

• I reject obvious sales pitches immediately

• I evaluate the rest based on mutual interests and potential value exchange

Important: Every rejection actually hurts the other person algorithmically. Be thoughtful about this.

When starting out, accept most connections. As you grow, become increasingly selective.

The DM Dilemma: The Hardest Challenge

Direct messages are where most creators struggle the most. I’ll be honest, I’ve missed genuinely valuable opportunities because they got buried in my inbox after viral posts.

Here’s my evolving approach:

1. Time-Block DM Review: Set aside specific times to process messages

2. Prioritize Personal Messages: Look for those that show the sender actually knows who you are

3. Scan for Opportunities: Search for keywords like “opportunity,” “collaboration,” “speak,” etc.

4. Template Responses: Create templates for common inquiries to speed response time

If volume becomes truly unmanageable, consider having a trusted assistant screen messages. Yes, this is a luxury, but as your brand grows, protecting your attention becomes an investment, not an expense.

Several AI tools are emerging to help with message management. Our team is currently testing a few and will share our findings in the community forums.

The Ultimate Mindset Shift

As your influence grows, incoming engagement becomes both a blessing and a burden. But it’s a sign that what we’re working toward is happening—people are coming to you rather than you chasing them.

Some people want to be near your energy. Some want to work with you. Some just want to feel heard by someone they respect.

All of these are valid, but not all deserve equal time.

The most successful personal brands aren’t the ones who respond to everyone; they’re the ones who make everyone feel responded to.

Master the art of perceived attention while protecting your actual attention.

This is the path to sustainable growth and genuine impact.

Before You Go

Everything above assumes you’ve got content worth engaging with in the first place. That’s the part most people actually get stuck on, not the engagement strategy, but the blank page that comes before it.

Which is exactly what I’m teaching in my free masterclass this July: how to never run out of things to talk about. No frameworks to memorize, no optimal posting schedule, just how to turn the work you’re already doing into a steady supply of ideas worth posting. It’s free, and there’s no catch: save your seat.

If you want to go deeper on the bigger game, the art of making everyone feel responded to while protecting the attention you actually have, that’s the whole subject of my course, The Art of Personal Publicity. Use the code LinkeyDink for 35% off.

And if your problem isn’t the strategy but the writing itself, if you want the posts and comments that earn this kind of engagement to actually land, Copy Hunter is where I teach that. Use the code PRESALE and it’s yours for $75.

The most successful brands don’t respond to everyone. But they do show up worth responding to. Start there.

—Justin