Hi. It’s been a pretty inconsistent summer as far as newsletter output, but consistency was never a part of this. that doesn’t mean I can just got dark for a month.

Not without explanation at least.

The problem is I’m stuck in a vicious cycle.

90% of my business comes from this newsletter. So when frequency of publishing goes down, inbound works goes down. And when I am working less, I have less material and less left over thinking that can be used to write the newsletter.

Beyond that, I have been doing a lot of thinking about what it is that I want to be doing in the future. By moving to the Pacific Northwest, I moved away from the hub of my industry. Less and less desire for remote and very few agencies where I live.

So I have been doing more and more work directly with brands. Which has been a lot of fun and super fulfilling. A lot of Go To Market work. Some campaign and brand strategy work.

But as I have been intentionally leaning into this shift, I have been doing the whole thing where “in order to be seen as a product strategist, it would help to be making products of my own”

And of course the “those who will be in demand are those who are proficient at using AI to build things” approach as well. And I’ve shared some of the things I’ve made here.

But I was talking with a friend yesterday who is a PM and has been given the directive to implement AI into his workflow more and more. And he said something that I have been feeling.

At first it’s enthralling because it feels like you are making a lot of things you never would be able to before.

But at the end of the day, you have the same feeling as if you had been scrolling on your phone all day.

And even worse, we both agreed that we also had no real memory of the process. We can’t look back and reflect on the steps we took or the places we had to troubleshoot.

All to say, it’s easier than ever to generate things into existence. But that is not the same as creating things. And I wonder how much damage its doing to conflate the two.

As is often the case here, no real conclusion to this thought. Other than the fact that the more I “make/generate” things with Claude, the less I find myself actually thinking and therefore the the less there actually is to go out into a newsletter.

Started as an update on where I’ve been, morphed into an observation that I felt like sharing.

If you want a much better articulated version of the same line of thinking, see Santi Pochat's new newsletter, where his second post unpacks this through his lens.

If you want to work together, reach out.

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Anyway I have had this saved for a while, because I find it funny.

And it got me thinking, what would the creative brief version of this look like?

So I made this:

But that then got me thinking, what would an actually helpful version look like?

So I made this:

¯\_(ツ)_/¯

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https://media.cordite.org.au/a-website-is-a-zine/

This is a kind of website I like a lot. It is designed as something you experience rather than visit. This particular one Tegan Webb’s conversation with themselves/you about how websites are kind of the same thing as zines.

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https://papermau.blogspot.com/search/label/paper%20toy

This is another type of website I enjoy a lot. A hyper specific reference for a niche skill / activity. This one is an archive of patterns for making paper art

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I really liked this article from Itsnicethat about whether or not the “fake” art made for movies can be considered real art or not.

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Honestly this list of 68 reminders for Junior strategists isnt just for juniors. some things in there we all need reminding of…

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Also really like this list I came across. Not much I would change.

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I’ve had people ask why I call myself a consultant rather than a freelancer. This visual sums it up nicely.

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And a visual guide to remind you that category should always have a heavy influence over strategy choices made

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Also came across this recently and while the whole thing is worthwhile, the distinction made between the middle two are the most important but most often forgotten thing

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WEEKLY MONSTER

No creation of my own this week, but here is a photo I took recently that cracks me up

Latest project has come to a close and I am available for freelance work starting next week.

Have something going on? Let’s chat.

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At least 50 of you make art of some sort. Which is more than enough to do a subscriber art showcase.

Next step, please reach out if you would be interested in participating and include some photos or links for where I can see your artwork. For now this is likely to be a digital showcase, so pretty low lift.

let me know: alex@stratscraps.com

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there is an excellent are.na plugin called tiny garden that turns your are.na channels into websites. Not something I need, but definitely something I am glad exists.

see here.

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As AI modals improve, it is important to remember this:

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remember to go back and revisit old notes. They don’t always need to make sense to be valuable.

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Cultural Cartography

Reassembling the Strategist

Lets start this off with the TL;DR…

Read more

a year ago · 95 likes · 8 comments · PK Lawton

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Most of us probably could benefit from reading this:

The Beautiful Mess

TBM 429: How To Thrive At Work When You Think Too Much

This post is important. It is the introduction for a book that’ll I’ll probably never publish. Why? I already have! I’ve written it across countless TBM posts (multiple books worth), but have had trouble getting to the crux of it. Over the weekend I had a breakthrough. It has been sitting under my nose with posts like…

Read more

2 months ago · 122 likes · 8 comments · John Cutler

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from an old issue:

Super important and often forgotten:

Just because someone is saying something you don’t like, it doesn’t mean they aren’t on your side.

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Tips for being a better strategist:

• ONLY ONE FRAMEWORK AT A TIME.

• STOP TRYING TO PROVE YOUR WORTH

• OPEN WITH THE DECISION, THEN BACK IT UP.

• DON’T BE PRECIOUS, BE USEFUL.

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The Creative World’s Bullshit Industrial Complex

This is an article from 2016 that has shaped everything I’ve ever written since. Maybe for the better, maybe not. It has definitely made me more hesitant to add a take.

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At some point, if you are a regular user of a tool like claude or chatgpt, your LLM account is likely going to know you and how you work better than any other person or algorithm.

So I asked my claude account to write me a reference letter, based on an honest assessment of everything it has access to. The output isn’t bad. There are a few things I wouldn’t have wanted in there if I was making my own promotional material, but I have kept them in for the sake of the experiment. See here what my claude account thinks of me;

http://claude.stratscraps.com/

i was pretty impressed with the image selection for the top image as well…

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4 presentation frameoworks

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related:

10 page deck format

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a guide for feedback in Creative reviews from my time at AnalogFolk:

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An important read IMO. Peter Drucker’s “Managing Oneself”

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TRYING TO LEARN MORE ABOUT PRODUCT STRATEGY? ME TOO. HERE’S WHAT I’M READING AS A STARTING POINT:

PRODUCT STRATEGY DROPBOX FOLDER

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↪️

However, please remember that as a strategist, the Insight is likely the least important part of your job. It helps sell strategy, and can help identify a strategy but it isn’t needed to land a strong strategy and often distracts or misdirects.

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I always wanted to explore some of these (original source unknown), but I couldn’t be bothered to type in each url one at a time. So I made it into a website.

https://stratscraps-ad-toolbox.netlify.app/1

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New Creative Concept framework:

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Here is stratscraps newsletter from a few years ago that was pretty good.

WEEKLY MONSTERS

Top L to R:
a table at a bar, a paper chili, great salt lake (which I never knew was half red)

Bottom L to R:
A praying mantis, another airplane shot, heavily edited, a monster cutout hiding with the tools of his own creation.

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https://art.stratscraps.com/

I’ve got to free up some storage space. Here are a few of my collage pieces that I am selling for $25 flat if you’re in the U.S.

Sorry to everyone who bought one for $100 in the past.

I’ve got some availability opening up.
If you are working on something that matters and need to make sure it seen and remembered, lets talk.
If you are in need a strategy input or guidance, lets talk.
If you want to work together, lets talk.

let’s talk.

alex@stratscraps.com

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The most fulfilled I’ve ever been during my full time career was after causing the loss of a big pitch.

I had been on a hot streak and was winning new biz pitches back to back.
I had just secured the agency’s biggest piece of business to date, then doubled that business after presenting in person to the clients.

On the heels of that, a piece of new business came in and I took a big swing.
I didn’t toss the client brief but I flipped it in a way that aimed to make a boring method of promotion interesting, by applying it in an unlikely place. Not what they were looking for.

But it was my loss to own. I felt real bad for the head of biz dev who lost out on the commission after fighting to free me up to be on the pitch team. And I don’t like losing.

But we lost because of my choices. And that was fulfilling. Because it meant I had the ability to make real choices.

Those choices weren’t going to get a win every time. But there was enough trust present to let those choices be made.

Lower stakes more day to day example of the same idea: The decks I presented had my flavor on them.

there were section headers like this:

with content like this

And it was incredibly fulfilling.

I guess the point of this all is that wherever you are, think about career progression or even job satisfaction through the lens of being allowed to swing and miss.

Because when every dept. has a thumbprint on the strategy deck, the losses are always abstract and a result of convolution, rather than a swing for the fences.

The single best way to judge a job is if you are allowed to own thinking and how you are supported when that thinking misses the mark.

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via: learning for people who prefer not to be taught

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we often think about strategy through the lens of problems.

Last night my dog was snoring. that was my problem.

And I realized there were different categories of ways to solve it…

Problem: dog is snoring

Solution: Throw something. temporarily solves the problem.

But I realized I was at the problem reactively. I was trying to fix, when most brand level problems (ideally) are more about trying to look at how to thrive in the face of a problem vs solve it.

(e.g. Problem: southern comfort doesnt do well on premise because of the social pressures that exist in the category… you cant solve those pressures, but you can use them as a way to show southern comfort as a signal of confidence)

So now I was thinking about the problem like this:

Problem: dog snores

Solution… put ear plugs by bed. Doesnt actually solve the problem, but helps me navigate my category landscape.

(can you tell I didn’t sleep well?)

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While I was laying awake, I was thinking about my role as an independent consultant. I wrote the following:

I’m a guide. Results are better bc I was along for the ride

I’m a technician. I make things more effective

I’m a driver. I’m a partner. I’m a mechanic. I’m embedded outsider. I’m a point of view. I’m an answer.

Does hiring me make things better, faster, or different in a specific way? Or is it more like a flavor? The output or the process? Better to be one of “many” who can do well whats needed or one of a kind who can make things that wouldn’t otherwise be made?

Answer:

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I continue to love 2x2s as thought devices. Here are a few recents;

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I wonder what is better, [insane but logical] or [calm lunacy]?

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this feels relevant to strategy somehow

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WEEKLY MONSTER

Technical drawings are a monster in my mind. Why are they so hard??

there is also an interesting little stratscrap bit to be written about concept drawings vs technical drawings. but my schematics vs diagrams may have covered off on that point?

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Admin updates:

I am wrapping a project and have availability starting in July.

There are a few ways we can work together:

• You can buy my time, i.e. the traditional freelance model. If you have a project coming up with the need for brand/comms strategy thinking and implementation, lets talk.

• Flat fee offerings. Read more here.

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Do you make art? In the past I have buried this at the end of the newsletter, but I am thinking about what a subscriber art show might look like. So, do you make art?

Based on the numbers the above poll comes back with, I’ll think through what would come next.

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Website was recently updated. More updates to come there, as always.

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What are we trying to say? (Strategy spend your time here)

How are we going to say it? (Creative spend your time here)

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From a good list of creative qualifiers to bring to your next creative review.

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Found this on Are.na, but thanks to some excellent distinctive assets I know that this was originally shared by Praveen. (if you aren’t subscribed, you need to be)

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Some recycled content from newsletters past as I compile my next print object:

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on this week’s Last Week Tonight, John Oliver ended the show by showcasing a plumbing company that made its own ads. All of which were incredibly low quality movie spoofs. Here is an example from a commercial titles “Toilet Dune”

The point is – we spend so much time trying to land the perfect concept, tone, message. Maybe there needs to be more room for novel experimentation. I really like the strat scraps logo I made. And I never would have made it if I knew what I was doing. Toilet Dune is fucking hilarious. And says very little about their ability, but I would totally hire them. People (and companies?) who don’t take themselves too seriously seem far less likely to rip you off.

SNL’s most popular format, the digital short, came into existence because Andy Samberg had a video camera and liked goofing around.

And you know what– this leads to a lot of bad content. But this isn’t Sundance. frequency is a huge part of effectiveness. Yet we spend 6-12 months with clients trying to land the perfect thought.

During that time, Radiant Plumbing released 18 commercials. And are being rewarded with free coverage on a show with over 500,000 live viewers and 9 million subscribers. The second most popular show on HBO.

I guess what I’m saying is… Can we stop trying to make things perfect and more things that are just fun?

Can we stop taking it all so seriously?

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At the intersection of hot takes and conversations I’ve had with subscribers,

someone said this to me recently:

“as i got better at thinking as a strategist, i got so much worse at thinking”

Thanks Amyri, that thought keeps messing with my head.

(other notes from that conversation:

“strategy is something to be implemented, not executed.”

“my favorite part of the job is a minority of what the job is”

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This is especially true when it comes to something like the 4Cs.

Here’s how I see it:

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The 4Cs are a nesting doll.

A company is part of the category.

The category is defined by the consumer.

The consumer exists within the bigger culture.

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So, to visualize it another way:

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Creative Brief: Complete Owners Manual

An overview of the creative brief that looks at it in context of the bigger process and the role it is meant to play – not just the information it is meant to contain.

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Two Freelance Truths via Tom Critchlow. I’m realizing the reason I feel so comfortable in a freelance role is because these have always been part of my core approach. (Emphasis mine)

THING ONE

Questions and inquisition are at the heart of good consulting - you can’t truly know the problem until you understand:

What the client thinks the problem is

What the actual problem might be

How the current system operates

Why the current system caused the problem

Why the current system can’t solve its own problem

THING TWO

Consultants are ideally capacity builders who develop links between research and practice rather than problem solvers. They provide methods and tools to help others expand their capabilities and skills on an ongoing basis, thereby transforming concepts into practical know-how and results.

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Some patterns and other fun stuff:

Now that I’m getting more and more data from Creatives for the Creatives on Strategists survey, a few things keep popping up.

1. Thought starters: Controversial item. Rarely appreciated, but I feel there are complex reasons as to why.
   

2. Talk less. This applies to people in general to be honest.
   

3. The purpose of a creative brief: answers are either “inspiration” or “clarity” – but more interesting is the tone of answers across the board. It can be summed up with this one response:
   
   
   “I gave up on those a long time ago. I’d rather just ask the questions I need answered.”

And my favorite response so far:

Q:What do you wish strategists would do more of?

A: Micro-dosing.

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I find myself reflecting on what makes a good presentation a decent amount.

Is it “that was productive” or “that was well received”?

Sure, ideally it’s both. But design for the former and hope for the latter, not the other way around.

Well received is the wrong pursuit.

Ask instead how things were moved forward².

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ill-gotten goods

100 things I learned in advertising school

Rory Sutherland’s alchemy

Brand thinking and other noble pursuits

How not to plan; 66 ways to screw it up

WEEKLY MONSTER

I want to see a campaign where the art direction is entirely art made by 5 year old using procreate for the first time.

years ago, Yancey Strickler, former CEO of Kickstarter, wrote an essay called “The Dark Forest Theory of the Internet” – it was read widely by a certain sub-type of internet people and sparked a publishing project and several other projects related to the idea of small, digital community spaces.

Well 7 years later he released the “Dark Forest Operating s…

Read more

Digital Gardens.

Community Spaces.

Dark forests. etc.

Different ways to explain that mass platforms like facebook are becoming less preferred to smaller, more community oriented places like newsletters. Or discord/slack. Rob’s Salmon Crew whatsapp group, or Yancy Strickler’s (Author of the article linked above) newly released DARK FOREST OPERATING SYSTEM (DFOS — more on that in a sec).

And its cool. I like the shift. But we also have become accustomed to abundance and personally I still love the internet for its biggest strength– discovery. But I am starting to see the tension. You can’t join every small group you stumble across. A community starts to feel lifeless if half the members are there because they joined after finding it but don’t have the bandwidth to contribute.

I suppose any neighborhood has involved neighbors and others that lurk in their houses. But I wonder how many small digital groups one can be a part of before checking them all becomes too cumbersome?

No real end thought here, but worth thinking about what we will give up to find true community. We can’t belong to everything? Or maybe in the far future, groups will consolidate and merge like corporations. Venture capital will get involved and the whole era will be over.

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But that said, if you are a paid subscriber, keep an eye out for an additional email coming your way today. It is a DFOS space I created for those who have chosen to pay. Not a ton there will be net new, but it will be a single place to find a lot of the higher value resources/tools/experiments I have shared here over the years. It also have more of a community space orientation with the option for anyone to ask everyone else a question/for sustained conversation etc. Just something I am trying out, bare with me as we find out together what is most useful.

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Found myself flipping through the strategy scrapbook recently, and there were a few page spreads that I continue to enjoy every time I see them and/or repeatedly find value in.

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This of course put me down the path of revisiting similar things I’ve put together in the past and I forgot how much I liked the "77 bits from the past 100 emails”

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Working on the equivalent for emails 100-200 now.

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In the spirit of nostalgia for me and sharing random shite with you, here are some screen grabs from old decks.

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Laughing to myself because this works great for certain types of clients and agency people as well.

Whats interesting is this was way more true prior to going freelance.

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This is worth a read. And thematically is relevant beyond its subject matter.

Quiet Media

The Computer Room

Everyone seems to agree that the solution to digital overload is to go offline. Log off, girl. Disappear for a while. Touch grass. While well-intentioned, this advice misunderstands the problem. The problem isn’t that the internet exists, or that we spend too much time on it. It’s that we’ve allowed one system to absorb too many roles at once. The inter…

Read more

8 months ago · 29 likes · 10 comments · Charlotte Rubesa

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Speaking of worth a read; Ben Duhl’s recruitment company blog remains one of my favorite examples of the format. One where the value is less about the content of the post and more about how the content relates to you and your situation in the moment, making it worth revisiting every so often.

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If you work in advertising, you are a thief.

Fight as hard as you can to give something worth what you take.

The good (?) news is the better what you leave behind, the more you are able to steal.

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worth a save: What makes a good question?

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I like this inversion of which part is the hard part.

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Reminder: if you use AI in your work, it is still just a prediction engine….

WEEKLY MONSTER

Some old creations that kind of sum up the whole vibe.

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A few new things live this week:

The scrapbook is now also a website. This will be something I iterate on so if you visit and the site is down, it means I’m pushing something new. Or it means something is broken I guess.

scrapbook.stratscraps.com

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I also catalogued all 200+ issues of the newsletter and built a little tool around checking the archive for its opinion on any given topic.

research.stratscraps.com/

Because this one burns tokens every query, it is something I am making available to paid subscribers. That group of people who have been paying monthly for absolutely nothing different, this is for you.

I’ve always said that the newsletter will always be free. which is true. But as hosting costs, survey fees and subscriptions stack up, I’ll likely start sharing my various vibe tinkering with those who have opted to become a paid subscriber.

If you’re not a paid subscriber but you’ve helped out with a one time or recurring “buymeacoffee” – reach out I’ll get you on the “approved” list.

If you are a paid subscriber and are having trouble getting access, also reach out. things are almost guaranteed to not work perfectly.

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This one isn’t as new, but is improved.

scrap.cards, which is a collection of one liner thoughts, tips, advice and other ephemera that is meant to be flipped through at random. something I’ve been doing for my own thinking for years.

This one also burns tokens any time the “collide” button is used or the Antagonist or Diagnosis tools in the header. Expect this one to be locked to all but paid subscribers soon as well, but I dont have the time to do so right now and I am already behind on getting this email out.

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And a reminder of “older1” projects:

WRKFLW: a super in depth prompt builder for you to use with your own LLM of choice.

Stratscraps.net: all original writing from the newsletters organized by theme.

Creatives on Strategy site: all the data as a lightly interactive website.

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Related to the above… The line between creating and consuming is blurring.

When people are skipping Netflix to instead vibe code something –for fun or function– that ultimately gets abandoned; is that creation or consumption?

A further push of the thought; I had a 4 hour drive recently and had Claude write a transcript for a podcast to occupy my drive. I then turned it into an audio file with text to speech software. It was pretty good. But is that creation? I don’t think so. It was definitely consumption, and the most extreme version of “personalized.” A filter bubble of 1. And I did make it exist. But I don’t feel like I created it.

Side note: it was pretty fun listening. I asked for 10 chapters, covering topics like Sci-Fi fiction, Geology of the landscape I was driving through, history of modern philosophy, A western genre critique of capitalism… But because I used text to speech, there were no real breaks or pauses between chapters. So I kind of had to guess what chapter we were in at any given moment as they bled into one another. In some ways, it heightened my degree of engagement to be actively trying to figure out if what I was listening to was fiction, non-fiction, or hallucination.

It was like one of these newsletters in audio form. Kinda cool.

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the start of every project/freelance engagement:

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Vox’s The Year Explained was pretty good. Despite the overpromise of the headline.

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More no code software inspired thinking: If you learn to build the container, does the nature of what you put inside it change? What does it mean to author both the text and the body that holds it? What is gained and what is lost?

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Platform —> Community. An are.na x craigslist personals mashup

Really interesting example of niche community building.

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This is actually a finding from the claudecast I made for my drive…

I guess they used to staff poets in fire look outs. Keroac even did it. He left his 6 month stint with his mind in rags then a year later wrote “on the road”

But what a cool thought. “Hm we need to find people willing to spend long periods of time alone in the wilderness – wait, don’t writers already do that? Let’s invite them to stay in the lookout towers.”

An example of something that sounds like it should have been the product of a good brief but was probably just a moment of clarity.

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Something I’ve learned from freelancing and repeat exposure to constantly unique assignments: one of the best places to start is “the constraint”

I still broadly operate within the "1. Diagnosis, 2. Guiding Policy, 3. Coherent Actions” framework, but Constraint is the starting point of the diagnosis.

And often, the constraint becomes the brief.

Makes me wonder if “the constraint” shouldn’t just be a standard box to fill in on any given brief template.

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A couple one liners I jotted down over the course of the last few weeks;

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Without a log line, it’s just a mood board in a trench coat.

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Less idea. more consequence

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Is strategy nouns while creative is verbs? or maybe the other way around.

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CAAS: Clarity as a Service.

WEEKLY MONSTER

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I’ve been toying with the idea of a subscriber art show. If you make art, and would want to participate in something like this, let me know. alex@stratscraps.com or drop a comment.

If there is enough initial interest, I’ll ask again but at the top where most people won’t miss it.

While we were in New York I was impatiently waiting for the family to get ready to go and picked up a book from my aunt’s bookshelf. It was about mindfulness on the go and the page I opened to was called putting down the spoon. In short, it asked that one try to put down the spoon/fork onto the table between every bite.

That is hard for me. But not just with my food. I once had a manager call me “hyper-efficient.” – she didnt mean it in a good way.

But in a lot of ways, I think that is the job of a good strategist. We are given a hard time for slowing things down, but in some ways that is the point. As long as it is intentional.

Well hold on, before we kick off, why is this what the client is asking? Whats the problem behind the problem? What is the thing that all the work should do?

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A risk with AI is that it tempts us to work faster. Look at how much I can do in so much less time!

But that is kind of like shoveling cereal into your mouth. But worse, because everyone has to deal with the indigestion.

What would it look like to intentionally work with AI in a way that slowed you down? Or to do strategy work in general one bite at a time?

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While product hunt is mostly drowning in every iteration of AI related anything these days, there are still little nuggets of gold there like this:

As long as people keep making things like this, I am happy.

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A quote from an academic paper I somehow stumbled across:

In this paper, I claim bullshitting is a social practice. I will argue that in particular speech communities people are encouraged to play the language game of bullshitting, and when it is played well it can bolster their identity. Under certain conditions, bullshitting is relatively harmless and can even be beneficial. But bullshitting can quickly spiral out of control and take over an entire organization or industry.

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Legitimate question: what are the “tricks of the trade” in advertising or strategy? do they vary person to person or is there a standard set of trade tricks?

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new briefing deck cover page.

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Top-down analysis or bottom-up pattern assembly?

When doing research, be intentional about which you are doing

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Got an email from a subscriber recently that included a paragraph that felt important to share. Sorry Greg, hope you don’t mind.

“When has taste... not been important? ‘Taste’ has also historically been situated in class/power. And it’s the Silicon Valley/tech bros (the dipshits building the new incredible and exceedingly problematic tech) who are in power, and proclaiming that taste is the only thing, and golly gee, they’re the ones thinking it’s theirs to define.

I can’t think of a group of people whose (cultural/aesthetic/creative) taste I value less lol.

The ability to articulate one’s own taste (and values and knowledge and expertise and opinion) is certainly an important thing in the AI age, with prompts, harnesses, agents, blah blah blah.”

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in many ways, this to me is the perfect ad:

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To a shareholder, this is a valid strategy:

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In theater, the dramaturg is the person nobody in the audience knows exists. They don’t write, direct, or act in it. But every good production has one. Their job: research the world of the play, challenge the director’s assumptions, identify structural problems, and ask the questions nobody else is asking.

Their contribution is invisible in the final product, but the production is measurably worse without them.

A dramaturg also doesn’t get hired for a specialty — they get hired for a production. Each one is different. The value is the method of engagement, not the domain. they are defined by how they engage with a problem, not any one deliverable.

Sound familiar?

Just wish is wasn’t such a silly word, or thats absolutely what I would call myself.

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speaking of myself, I had claude do some work around weaknesses in my approach to freelance. The output isn’t bad.

lol at the fishing metaphor though..

also, I still think I prefer to be upstream. but the diagnosis thought is interesting.

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I’ll end with something pretty disappointing from Substack.

When writing a newsletter, you have a header of options for things to include:

Under more, I noticed this time around there is now a “prediction market” option…

Sure enough, it is a polymarket promotion dressed up like a feature..

As if we needed another sign that late stage capitalism has a full chokehold on modern culture..

FWIW I am actually not 100% against platforms like this (maybe I am I dont know), but the things that end up getting bet on are often pretty dark. John Oliver just did a full segment on it that is worth a watch. But moral judgements of the platform itself aside, this feels like a weird feature for substack. Why would anyone need that?

Weekly monster

This is pretty far from the original intent of this section. But these are doors to my back yard I removed from my house with my dad. If there is one activity that will reward slowing down and punish short cuts, it is anything building related. Making art you can get away with errors. Not so in a door frame.

What is the strategist version of “measure twice, cut once” or do we not have one? We should.

A longer than typical wall of text to open things up, so off the bat, I want to call two things out.

1. I was booked out into the early summer but had something fall through and am now available for freelance projects. Have something coming up? Let’s talk.

2. On a similar note to the above, but more related to the below, I am working on a few different things to translate my ever growing archive of thought and collected knowledge into something of more direct value. But I need to put some stuff to the test. If you are currently working on a brief or other piece of strategic thinking, and would be willing to (under NDA or whatever is needed) share what you are working on, I would love to offer some free strategic support in exchange for letting me plug specifics in and seeing what comes out.

   That’s pretty vague, I am aware. Read on to get some additional context – or even better, reach out.

Ok, here’s the aforementioned block of text…

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Thinking is a transaction.

And, just like cash transactions, thought transactions often have left over change.

And that’s kind of what this newsletter is. A change drawer.

But what’s cool about a change drawer is that, not only does each quarter have value tied to specific occasions, but also, over time there is a cumulative effect where the collection of change becomes more valuable than the sum of its parts

(Ok with a change drawer it is exactly as valuable as the sum of its parts, but you know what I mean.)

Where I am going with this is that, until recently, I didn’t really have a way to extract more than one metaphorical quarter of value at a time. And I continue to share this newsletter in the hope that any given issue will have some piece of “thought-change” that is worthwhile to someone else as well.

But there is also the corpus of knowledge in total. the full jar of change.

I’ve been playing with how to tap into that value as well.

For example…

• The initial WRKFLW web app which built better prompts for one to then use in their own LLM tool of choice

• The above also evolved into a WRKFLW Pro prototype: A brief-building web app that forces you to diagnose the problem before you write the brief — AI generates strategic options at each stage, you curate and select. It is built on an aggregate of my thinking/writing about strategy, then shaped by Rumelt's Strategy Kernel and Martin's Choice Cascade. Prototype only uses Haiku, but would eventually upgrade.

• Scrap.cards: A shuffler of collected quotes. But now has an option to pull two quotes/notes at random and describe how they intersect. Not useful in a targeted way, but interesting.

• Creatives on Strategy: A deeper analysis of the Creatives On Strategy data, that updates as new responses come in.

• StratScraps.net: a searchable database of a lot of my original writing that has been featured in the newsletter over the past 200+ issues.

All the above have been about learning how to best tap into the value of the jar of change. Artifacts of my own exploration. There are also a couple things I keep just for me, built in claude as a type of additional layer of though:

• Strategic Recall — searches my vault of newsletters, notes, saved documents etc, for what I’ve already said about a topic and makes connections to current work.

• Brief With Context — thinking partner mode that’s grounded in prior work rather than generic strategy thinking.

• Category Reader — reads a category’s cultural and semiotic landscape, looking for patterns that connect to existing notes or observations.

• Cross-Pollinator — searches across active projects, archive, and reference library to surface connections between unrelated work. The “this client problem is actually the same pattern as that newsletter topic” finder.

• Tension Developer — takes a half-formed observation and develops it into a structured strategic tension, drawing on my established thinking about how tension works productively.

• Brief Red Team — stress-tests a finished brief from four angles, informed by patterns from past client work.

• Taste Calibration + Design Aesthetic — encoded profiles of how I judge, decide, and reject — so every output matches your sensibility, not a generic one.

You’re still here? cool. Well there is lots more to share this week so thanks for sticking with me through that.

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Are you looking for a talented freelance comms strategist?

Madeline Dooney is a comms strategy director who been at Vice (where we worked together), Droga and Mother. And she decided to go freelance recently.

I am actively looking for my next project and if someone told me they had a comms strategy need, I would tell them to call her.

See her site here.

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More gangster thinking coming out of the Day One team;

They recently launched Side Projects.

Similar to the Day One Almanac, there is a print component that you can order for free here. And a substack as well.

But the most fun part is that they shared some of the scraps and byproducts that came from the process of creation.

Looking at the above gif and I see a high design object that I want to acquire. But then looking at the pieces that made the final thing possible, and it reminds you that all any of this is is just continued collecting of thoughts. Building out ideas and not letting napkins get thrown away.

This is something anybody can do if they have the ability to look at something and have a point of view, then follow through to see that POV get fleshed out.

I am excited to share this because the content is really good, but also because that is the whole point of this newsletter. Even connects to what I was going on about at the top.

Collect your thoughts. Save them. use them. Make things.

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these are my rules too.

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“Specialization” is often framed as something you do on purpose. That may be true for some. For myself, I’ve found that specialization is something that happens to someone. It is a result of momentum and circumstance (two highly intertwined concepts now that I think about it).

Personally, About 8 years in to my careers, I looked up and I found myself specializing in booze advertising without really meaning to.

But since going freelance, I have actually done a lot less alcohol and found myself specializing in certain moments of need rather than categories.

For example, in 4 years of freelancing I have done more Go-To-Market work than I had in the previous decade of my career.

But it hasn’t all been GTM work. The other two moments of need type work I have found myself immersed in frequently are the “We don’t know where to start” assignments and the “we’ve been at this, but something isn’t working” moments.

And honestly, I really like that last one. Not because I like being a hero. Often I am not. But as a freelancer, it is one of the most pure assignments, because it is an instance of being hired TO find the constraint and then suggest next steps based on the constraint itself.

Too often the work is more about acknowledging the constraint in whispers and trying to push past it without ever addressing it head on1.

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The child's clarity and the analyst's rigor are mutually annihilating forces.

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When getting a brief approved, we design it to survive scrutiny.

But, beyond clarity, its main job is to overcome indifference.

But the easiest way to pass scrutiny is to sand off all the sharp points that people get hung up on.

As long as its clear, having creative teams hung up on thinking about your brief isn’t a bad thing.

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Weekly Monster

I’m in NY this week which mean I got to see my very first original monsters.

[no magazine cover mock this week, because thats all thats standing between me and hitting send.]

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A thought from the archive: Padded Value. Technology has made it easier to pad what we present. more slides, data and "proof." But proof and trust are inversely correlated in creative work. The more you have to prove, the less they trust you. The less they trust you, the more you have to prove.

This is why I don’t cite sources.

(jk)

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One of the most important things but most hardest to learn in this line of work is to not just accept the feedback. Especially if it is coming from more than one source. The more sources feedback is coming from, the more likely swirl is impending.

For no reason, here is a math equation for it:

Probability of chaos = number of people giving feedback (nF) x amount of ambiguity (A)

or P(chaos) = nF x A

The point is, and I’ve said this before, ALWAYS be asking of yourself and the team;

• “What is this work meant to do? (which should tie to “how is thing being evaluated”)

• “What is motivating that feedback? What is being responded to?

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Something else I’ve said before: “Writing solidifies, chat dissolves.”

But I want to amend that.

“Writing solidifies, chat explores.”

Another one:

Problems don’t start where they first appear. A leak first appears inside, but the problem is a failure on the outside.

You could probably simplify further: problems are not symptoms.

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Finally got the Creatives on Strategy responses/synthesis up somewhere more interactive / easier to navigate:

https://creativeonstrategy.stratscraps.net/

Other ongoing surveys I have running:

A survey about fun at work (open to anyone in advertising)

A survey about working with Strategy Freelancers (open to anyone who has worked with freelance strategists)

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The whole conversation around “friction” as a new social value is interesting to me. Off the bat, I don’t disagree. It isn’t wrong…

But also its interesting that “friction” was what stuck in the discourse rather than something like “effort”

“Friction” is to “effort” what “User” is to “person”…

Said another way, Friction is an engineering word, while effort is a human experience. There is probably more to be said about that in and of itself.

But also, they aren’t exactly equal are they? Friction implies difficulty, whereas effort implies time and consideration.

Imagine saying “I put a lot of friction into this meal I cooked for you”

Which gets at something else interesting. You can’t “add friction” to something and make it more meaningful.

The most meaningful things nowadays are the things where the effort are inseparable from the process.

What that’s describing is “craft”

Have we already become such cyborgs that we have to describe the idea of having a craft as “friction” ??

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Sometimes I forget I have this. There is a “buy me a coffee” page I have set up as a way to gather the funds to cover various stratscrap costs (e.g. hosting costs and survey tools) no obligation to donate, but its a way to help me out that doesn’t require a paid subscription to the newsletter.

Community chest

WEEKLY MONSTER

(If you’re new here, this is neither weekly nor typically a monster. Although I’m overdue for some monster doodles.)

Taking up fly tying at the start of winter has resulted in a pretty silly amount of flies. But these are the ones I’m most proud of.

Within the world of typing flies, there are an ever growing set of patterns you are meant to imitate. Some are hundreds of years old, some are contemporary, but all but the most experienced fly tyers are meant to follow instructions.

I HATE following instructions. Some of the below are established patterns where I followed along some jobronie and his (and in one case her) youtube channel. But many are things I did just goofing around. And those are my favorite by far.

Will they catch as many fish? Who knows. At this point, this is more of a craft project than a fishing project.

But I will take it as a win that Apple Photos prompted me to look for other photos containing bugs when I was swiping through these.

Screenshot heavy this week. But a few original thoughts here and there to prove to myself I’m not a total hack.

(scroll to read) obligatory disclaimer: these newsletters are not really edited for typos or clarity. this is a place where I offload thoughts, in the hope they are valuable or interesting to others. typos and less than clear writing are a reflection of the function of this newsletter, not my ability to write. I can assure you I edit my work when I am being paid for it.

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Every now and then I catch myself doing the things I am constantly warning against. It’s easy to follow a process when you are there from the very beginning, but when you are brought into something already in the works, it is easy to slip into sharing work that shows you are up to speed rather than the relentless focus on clarity that strategy should always prioritize.

So a reminder to myself, but also to you… Always start with;

• The purpose of this work is ______.

• To achieve that, we will ________.

• My role in the process is _________.

• And it will be successful if _______.
  

Write it out. By hand if possible.

Think in terms of knowledge, clarity and decisions rather than deliverables. What decisions need to be made? What are the implications of each.

The challenge is more than likely you will not share any of the above with anyone. it is for you. But it will be a primary source for putting together the “narrative” that we are all so fond of.

And for every deck, meeting, brainstorm, doc, etc, ask of yourself or the team “why are we doing this? How does this push us towards the end goal?” (just you know, ask it nicely or propose the answer and see if anyone disagrees).

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btw, the dept of defense/Pete Hegseth spent $6.9 million dollars on lobster tail in a single month (source)

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This is also pretty much the ideal creative process.

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An argument for framing briefs as questions.

I can argue the other side. A brief is what we’re doing and creative is “how” – but I have seen enough evidence from other fields and smart people that suggest there is something to the question approach.

“your work shouldn’t try to solve the problem, it should present the problem” - Bill Hader on comedy

Where does that fall between the two? Because honestly I just want to do whatever Bill Hader does.

Also, the sentence “life is largely plotless” is great.

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I said I was working on some things as I learn to use claude code better.

The first thing I built is based on the WRKFLW PDF I shared, but a bit more interactive.

It is essentially a prompt generator. But a very long prompt that triggers the llm to start asking you a set of questions you should have answers to and then provides new information the build out a POV. (category audit, tensions, etc)

The catch is it requires you to use an LLM (and is built specifically for claude) I’m still trying to build a version of it that doesn’t require AI, but havent had the time to think that out much.

I also rebuilt my scrap_shuffler.

And an 8 page zine generator for making tiny zines out of a single piece of paper.

And finally started putting some of my collage work up on a website.

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Worth a listen: Jurassic Park Theme but 1000x slower

WEEKLY MONSTERS

Kiddo and I hid paper apples around the house. I guess at school they have hidden “creepy carrots” (which is awesome), so we duplicated it at home.

obligatory disclaimer: these newsletters are not really edited for typos or clarity. this is a place where I offload thoughts, in the hope they are valuable or interesting to others. typos and less than clear writing are a reflection of the function of this newsletter, not my ability to write. I can assure you I edit my work when I am being paid for it.

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Weaponized Strategy: strategy that serves an internal interest or agenda rather than in service of the effectiveness of the work

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Last time around, I linked to a pdf titled “A Decidedly Useful Guide to How Brands & Businesses Grow. But I gave credit to the wrong “Something Different” agency. So shout out to Gareth and his agency for putting it together. Sorry about that.

I also mentioned “Only thing that would make this better is if it were a website or google doc with an index and clickable nav links”

Two people took it upon themselves to ask AI to do some website making for them and shared the results;

• Greg Brown, SVP of Innovation at Omnicom, put together 5 different iterations of what it could look like. These all focus on presenting the information in an easy to navigate interface.

  

• Andrew Reeves, head of Strategy at The Royals, built a site featuring an AI chatbot based on the information within the PDF.

  

~

So shout out to both of you. that was cool, and has me playing with a number of different no code tools now as a result. Will share those outputs as they come.

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Its always hard to measure oneself against these types of things, but it is a fun and worthwhile exercise:

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Reading “The Art of the Gig” by Venkatesh Rao and came across this page that felt especially relevant to strategy…

I’ve often said that the role of the strategist needs to be more than just leading up to the brief. But never quite articulated when those post brief moments were. Every piece of creative work, especially commercial creative work with clients has periods of chaos followed by moments of respite. Except those moments of respite don’t feel like respite because they get turned into their own breed of chaos by internal spin and panic.

The role of strategy is to give structure and guidance to these periods of time post contact. To clear the fog of war1 and do a posture reset.

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I could of sworn I put this in a previous newsletter.2 But after brief and non comprehensive glance back in time, it doen’t look like it.

Anyway, “this” in this instance is the note I wrote to myself “The type of questions you can’t look up the answers to”

In a world where conversations are punctuated with “google it” or “let me look it up,” I always enjoy the puzzle of the type of question that can’t exactly be looked up.

…

What’s funny is I can’t remember what the question was that sparked this note3. So I tried to look up examples of questions that can’t be looked up. As you can imagine, that was a rabbit hole…

And now you have to suffer the consequences of me diving down that rabbit hole via a deep dive into epistemology reading and frustrating conversations with claude.

A question may not be answerable if…

• A single correct answer exists in reality, but there is no possible way to observe or record it with sufficient resolution. (Epistemic inaccessibility)

• The system follows rules, but the only way to know the outcome is to let it unfold step by step. (Computational irreducibility)

• The system is deterministic, but tiny unknown inputs dominate outcomes. (Chaos sensitivity)

• The act of measuring or asking changes the state being measured. (Observer interference)

• The answer depends on events that have not yet occurred. (Future contingency)

• The available facts support multiple incompatible answers equally well. (Underdetermination)

• The question refers to itself in a way that prevents stable evaluation. (Self-referential paradox)

• Different valid definitions yield different correct answers. (Definition dependence)

• Answering the question requires answering another instance of the same question first. (Infinite regress)

How to recognize these in the wild

If a question:

• sounds factual

• assumes precision

• survives rephrasing

• yet collapses under “what would count as evidence?”

Or my favorite:

A simple test

If a kid asks it and:

• it sounds factual

• adults hesitate

• science responds with “it depends how you define…”

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I recently listened to what I consider to be the best podcast episode of all time. You can listen below, but if the title, key image, or simply the first 30+ minutes of seeming nonsense turns you off giving a listen, the premise is that bike repair shops are indicator species for thriving cities, the way snails are indicator species for healthy soil.

Which made me wonder, what are indicator species for different types of consumer intel? It is a question that can only be answered with more context, but it is something I am hoping to apply to how I think about consumer insight in the future.

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Another random note where the original context escapes me:

“perceptual realism vs literal realism”

But I can immediately say that we focus on literal too much and perceptual too little. Even when it isn’t about realism but about being “relatable” to consumers.

Its more important to be perceptually relatable than to be literally relatable.

There is plenty to be explained here, but I don’t think its necessary. let me know if that is an incorrect assumption.

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This quote is fantastic without context:

From a Bayesian standpoint, it would arguably have been a mistake if she did listen to me. Skepticism of weird ideas is a kind of “immune system” to prevent us from believing in nonsense.

But the context is really good too; Rules for Weird Ideas

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Everyone wants to _______, but nobody wants to ___________.

e.g.

“Everyone wants to be strong, but nobody wants to lift heavy ass weights.”

or my own remix of the quote: everyone wants to advertise like liquid death, but nobody wants to release a full metal album with tracks with titles like “fire your marketing guy”

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Here is a collection of cassette tapes people have found, with the audio uploaded to soundcloud.

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My Dream job:
coming up with themes for This American Life Episodes

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Here is a pdf you can upload to claude as a project context and have it deliver some decent strategy thinking based on existing models of thought and outputting category audit, problem reframes, competitor audit, insights, propositions, core diagnoses, etc. It is a work in progress but however you use it, even if just reading the document alone, it will hopefully be useful.

If confusing, just upload the doc to claude and ask how to use it.

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”Proof denotes the end of inquiry, not the beginning.”

This is why leading with data is dangerous. You’re starting from a conclusion and working backwards. The data should validate, not dictate.

WEEKLY MONSTER

Making art with children is the absolute best.

The idea was to have some object of more permanence in recognition of v200. But it wasn’t coming together in a way that felt right.

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Oh look, someone1 aggregated all the most important evidence based thinking from top experts on how brands and businesses grow into one place. If you are a strategist – download this and read it once a year.

Only thing that would make this better is if it were a website or google doc with an index and clickable nav links2.

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Strategists could never be book cover designers. Every book cover would be like 20 pages long.

(related: itsnicethat feature on book cover design)

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Google is in cahoots with Big Cheese. I knew it.

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Without further context, which diagram would you say is more accurate?

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I wish there was public data that went with this. They did revive it a few years ago and made a podcast from the things they heard. I have not yet listened.

Additionally, I want more hotline-based creative, but I 1000% understand why we can’t have nice things in this instance.

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from:

https://deathtobullshit.com/

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I would have done better in school if my assignments were more like this set of prompts.

A sample of some of the 40+ prompts:

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A collection of screams:

https://justscream.baby/

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Time for the abrupt interjection of dissent rhetoric and resistance material!

Make your own ICE-Watch kit.

Here is the STL for a wallet whistle you can print if you have a 3D printer.

Then… you can also print a little 8 page booklet on a single sheet of paper like this:

Here is what my prototypes look like:

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Put a whistle and a zine in a ziplock bag, repeat as many times as you can, and leave them around town in coffee shops etc.

…

Currently working on a web app that would just let people write in boxes and have the formatting be done automatically. Stay tuned.

In the meantime, here is a google slides doc with some good boilerplate copy to get you started. Remember to change it the state specific details!

~

now back to the stuff…

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Weird tech patents is a trip to browse.

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“A student makes hundreds of pages of photocopies and takes them home, and the manual labor he exercises in doing so gives him the impression that he possesses the work. Owning the photocopies exempts the student from actually reading them. This sort of vertigo of accumulation, a neocapitalism of information, happens to many. Defend yourself from this trap: as soon as you have the photocopy, read it and annotate it immediately. If you are not in a great hurry, do not photocopy something new before you own (that is, before you have read and annotated) the previous set of photocopies. There are many things I do not know because I photocopied a text and then relaxed as if I had read it.”

Umberto Eco, How to Write a Thesis (1977)

… I see myself in this text and I don’t like it.
I also see our industry.

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You can’t do both at the same time.

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If you can’t tell, I went down a data/info viz rabbit hole recently. Starting collecting the purest art form: 2x2s.

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From an article titled “How do you coherently present a lot of content online?” on Itsnicethat, I saw this lil tip that I think applies beyond design:

“Keep the main layout and structure simple and clear. Add little irritating/fun/odd/nonsense/bleeding-edge features to the mix. Voilà.”

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A quote from William Gibson that caused some reflection:

“today, reliance on broadcasting is the very definition of a technologically backward society.”

The quote was written in 1999, but the underlaying premise of information distribution being the categorical factor for society is interesting.

WEEKLY MONSTER

Something old:

Something New:

✍︎✍︎✍︎

What a weird time to be writing about advertising. Feels irresponsible to pretend things are normal or ok.

One of the biggest mistakes we make is to view each new headline as standalone. That latest thing replaces that last thing.

But it is important to look at the whole. The aggregated sum total of what is happening in the united states at the moment.

So I took the time to compile a (running) list of confirmed news stories, facts, and resources to help me/you/us take a step back and see the FASCIST FOREST THROUGH THE FASCIST TREES1.

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A quick reminder: these newsletters are not really edited for typos or clarity. this is a place where I offload thoughts, in the hope they are valuable or interesting to others. typos and less than clear writing are a reflection of the function of this newsletter, not my ability to write. I can assure you I edit my work when I am being paid for it.

Anyway, on to strategy things…

Some of my favorite Sketchplanations…

~

~

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Shoutout Molly Barth for dropping this comment on last week’s newsletter; “I'd particularly be interested to hear about best practices around hiring junior talent. I think there's such a huge disconnect in the market right now between companies/hiring managers (candidates are lazy, unmotivated, lack social skills and professionalism, etc.) and junior talent (roles are so few, companies are asking way too much of them, want more work/life balance, etc.)”

I wanted so bad to have a clean little framework in response to this question. But my honest response is that when hiring junior talent, you are evaluating for potential over experience. Even when it’s not a entry level role. And so much of what you’re looking for is usually context dependent and about team fit.

BUT… IMO, potential can be reduced to a combination of two things;

1. Deep curiosity. Not that same as what they read or how much they read or what they already know. But the compulsion to want to know more about most things. And the tendency to question inadequate answers/explanations. A good measure of this is asking about what they have gone down rabbit holes on recently. Make it clear this doesn’t need to be related to work.

2. Ability to make something interesting. Have them create a presentation on a topic of their choosing. In the past I have used the literal prompt “choose an ordinary object and make in interesting” (see this example from an intern’s application. She ended up getting hired full time after the summer came to an end.)

If they have these two qualities, hire them.

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I think about this a lot when creative teams get feedback about the tone or message present in the work. REMEMBER – it’s not what is said, but what is heard/how it is received.

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damn there are some banger old ads out there.

Anticipated feedback these days:

“but the percent of our audience that likes onion sandwiches is negligible. We’ll alienate anyone who thinks onion sandwiches are gross.”

They ARE gross. thats kind of the point. You are appealing to people who think they have unique tastes of their own. And doesn’t everyone feel that way, regardless of how true it is?

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as much as I hate the word insight, this feels like one that would make for a strong creative brief:

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I love a good map that rejects the assumptions most maps make;

more unusual maps:

Wiki of map projections

20 of the Strangest Maps Ever Created

Which also led me to this fun article: Mapped: The boundaries of human perception

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I am obsessed with the idea of wonky variations of normal sports. Three sided soccer is apparently a real thing, with a world cup and everything. How much fun would it be for a brand to sponsor a team or tournament?

A fun exercise next time you are stuck in line and tempted to pull out your phone… what other sport variations would be fun to watch? Where is the line between ridiculous and entertaining. What is needed to keep a sport from becoming pure spectacle without long term staying power? Could soccer work with more than 1 ball? What about other sports?

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Florian Schleicher’s trends report on Friction is live, featuring yours truly, as well as a lot of really smart people. you can download here.

WEEKLY MONSTER

Sometimes photos turn out really cool because they werent what you intended. Yea, there is a moral there.

Subscribe now

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SOFT LAUNCHING STRAT_SCRAPS TALENT SERVICES

A long time ago, while with VICE/Virtue, I did some work with Indeed. The project was primarily supporting their Recruiter side of the business, and as a part of the process, I interviewed a lot of recruiters and thought a lot about recruiting. Around this time I also was put in charge of hiring our Summer interns, which resulted in working with two of the most talented junior minds I’ve met to date. And I’ve enjoyed every search and placement I’ve been involved in since.

I bring all this up because there is something new (for me) that I want to try this year. I would love to do some talent placement work in a more official capacity. Among subscribers I have smart people of all levels both looking for work and looking to hire.

People do this as a living by charging a commission. But because I’m just putting my toe in these waters, any jobs I’m able to help secure would be purely in exchange for the experience of it.

IN SHORT…

If you are hiring for a full time strategy role, lets chat – I’d love to help.

If you are a recruiter, I’d love to chat and hear about your experience and advice.

If you are looking for your next job… look out for more in the coming months, I am not quite ready for you yet.

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2026 is kicking off with two different things I was asked to contribute to.

1. The Recess Creative Playbook. This one is an annual must. TBH I wish I could re-do my contributions because the contributions of so many other folks are so strong

   

2. Florian Schleicher’s “Friction Reloaded” trend report. It hasn’t launched yet but catch it next week.

   

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Would your employer support/participate in a nationwide strike? Talk to them about it now so you know where they stand.

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buy some cheap whistles and hand them out. Here are more resources re; whistles as part of community defense.

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Tons of good resources here for general preparedness.

Report ICE plate numbers here.

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Back to the strategy stuff I guess…

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In Venkatesh Rao’s The Art of the Gig 2, there is a section that talks about management styles.

While not originally Rao’s concept, this was the first place I came across the idea of “Theory X” and “Theory Y” management. It was one of those moments where it seems both obvious in retrospect but also immediately reframes how you think about past experiences.

In short;

Theory X management believes that the role of a manager is to mitigate failure. Managers keep employees from failing or screwing up.

Theory Y management believes that left to their own devices, employees will typically do the right thing. Managers are there to promote growth rather than manage risk.

Thinking back, it’s pretty obvious which category all my best managers have been in…

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This Atlantic piece “Reading is a Vice” was interesting.

In short, the number of people reading is falling. Thats bad. So people are trying to get more people to read. thats good.

But the way they are doing it is flawed. The latest effort positions reading as a way to save democracy.

But the authors surfaces a really strong insight (i don’t use that cursed word lightly) – all the biggest readers they know have memories of reading when they were not supposed to. Of being unable to hear the world around them, or of the flashlight under the covers as a kid.

Reading is a vice. and thats a good thing. By positioning reading as something that can be addictive, it ups the odds people will want to get into it.

a more convincing approach than “read and save the world”

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A fun tool that turns any substack into a newspaper. A pdf version of the stratscraps print newspaper can be found here.

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Subscribe now

WEEKLY MONSTER

A few things this time around;

A few flies I recently tied. Interesting to like 3 of you, but learning how to create something new is always really fun.

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From the “anti coloring book” – in which the color is already provided and it is up to you to draw in the lines. Really great concept in a over crowded category.

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These have started popping up all over in my parent’s neighborhood. There is a local wood carver who has been carving faces into downed tree ends, stumps, and other dead wood in parks, parking lots and along sidewalks.

My favorite part of this is 1) the act of adding art/something interesting to the public space and 2) that it suggests there is a person regularly going around with a chainsaw and set of chisels looking for new exposed wood.

Share

Reminder1, I am freelancing again and currently building out my calendar for the coming months. I’m building out a bit more of a formal process based on what I know to be freelancer pain points, agency needs and so on. You can see this WIP document at the end of the newsletter, but in the meantime, feel free to reach out to talk about upcoming projects that might fall outside of that structure.

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I was thinking over the holiday about the idea of technique. As with a lot of my vacation thinking, it started with a thought about fishing (wait don’t hang up).

The thought went; there are many techniques when it comes to fishing. Each its own thing in its own right. Each has its own evangelists.

But there are a few different ways to think about how to apply technique…

The taxonomy of technique.2
e.g. fly fishing → types of flies → patterns → how to fish it.

Technique as a solution.
e.g. trout eat bugs that are too small to cast on a traditional line, therefore fly fishing was developed using the line as a way to move very light lures.

and finally the most interesting:

Technique as Identity.
e.g. Fly fishing becomes the identity, rather than the method.

This is abundantly the case with fishing. And I want to be clear I don’t actually think its a bad thing. Fishing is about more than the most efficient way to catch a fish.3

But what’s interesting is when you apply these modes to things like strategy.

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I think most of the time, we get caught in the trap of strategy taxonomy. We are put in a place where the process and the tools are set and all that we control is how well we can “cast”

And on the flip side, in an effort to chase specialization (and a tendency for contrarianism) there are many Strategists who identify as a ______ strategist, regardless of the species of any particular problem.

Technique as solution should be the most common, but that doesn’t always seem true. It requires diagnosing the problem first, then selecting (or inventing) the method. You have to approach strategy work like you're sustenance fishing. The gear serves the catch, not the other way around. (e.g. ok this problem requires I use this set of knowledge and material and tools).

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I fish because it’s relaxing and a fun way to solve problems. I do strategy because there are problems out there that can be fun to solve.

But you have to approach strategy work like you’re sustenance fishing. Don’t let the gear dictate the method.

(An argument in the other direction)

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More Work in Progress thinking:

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“Interstitial time is actually quite valuable. It allows your brain to rest from stimulation. It allows your mind to wander and maybe come across a new idea. It also teaches some form of patience.”

source

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“Any company that is not a tech company will be irrelevant,” said Oteh.”

from “Accenture Song has moved upstream of advertising” in Digiday.

I kinda hate this quote.

Not only do I think it is wrong, but I it represents a mindset that is dangerous.

Using technology does not = being a tech company. Are jewelers on etsy a tech company?4

All of this is tangentially related to a thought I’ve had in one form or another for a while. Technology is framed as changing the world all at once, but it is mostly a story of small conveniences.

Agencies, CPG companies, my own consulting practice – these are not tech companies. But there are many small conveniences offered by technology they seem to ignore.

You can use AI as part of your research process without being an AI company. You can build clients web portals to store deliverables and track timelines without being a Project Management platform.

Use tech. Don’t define yourself by it.5

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On average, Freelance Strategists are, well average.

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Thanks for all who took the time to fill out the short survey on their experience with freelance strategists. (If haven’t filled it out and frequently work with freelancers, I would love your input).

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A while ago I published the first round of findings (pdf here), but with new responses, I felt more comfortable doing some analysis rather than just response reporting.

And the main takeaway is the paradox of being a freelance strategist:

Agencies hire freelancers for fresh perspective → but they want freelancers to conform to existing processes and styles.

One quote sums it up especially well.

“I was going to say 5 because they always provide us with a fresh perspective... I marked down to 4 because there can be a disconnect.”

And the thing is, this is not an unfair expectation. But the breakdown comes when strategists see themselves as either “a part of the machine” OR “defined by their disruption” –and disruption of thought easily bleeds into disruption of process.

So what? Well, I can’t speak for everyone, but I can tell you that these results have helped shape the process I am building for my work in 2026.

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WEEKLY6 MONSTER

one of life’s greatest joys is leaving really weird shit around wherever you go.

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Finally reading east of eden for the first time. There is a character is who known for being highly inventive and constantly coming up with new ways to solve old problems. However he fails to ever make any money and dies poor because he gives his inventions away for free.

I could have made the following point without that anecdote, but it felt related.

Because it reminded me of a good strategist. Strategists have to be happy with the getting to sit down and think about a problem without ever getting rich from their work.

But inventors do something that strategists don’t. They concept. Creatives concept. Artists concept. Architects, builders, and nearly every other creative task requires a concepting phase.

And you don’t get a ton of push back claiming that strategy is a creative act. I could argue either side of that statement, but it’s not a controversial take.

But we don’t concept. What would a conceptual sketch or proof of concept look like for strategy? What’s the back of the napkin version?

Whether or not you think Strategy is comparable to invention or art or design – a concept phase would absolutely improve the outcome.

But instead we try and just brute force think our way into a final answer from scratch… Ok here is the research. Now let me just do some thinking, make a leap or make a choice, and the answer should appear.

That doesn’t seem right.

On the other hand, what exactly would a proof of concept for a strategy look like? It’s kind of a discontinuous innovation (e.g. like inventing the wheel – there were no concepts of the wheel, as soon as it is sketched, you have invented it. Fascist and aspiring feudal lord Peter Thiel calls this a “zero to one” invention.)

I’m not sure what the answer is, but I stand by the thought that strategy thinking should have a concepting phase of the thinking that involves more napkins and less rounds of review that water down the thinking rather than build it out.

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Feedback on Freelance Strategists in general:

Full results

Are you someone who works with strategy freelancers? Do you also have a second (ok ~3 min)? If you haven’t already, take the short survey here:

Freelancer Survey

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Some of my fav things from 2025 STRAT_SCRAPS:

»»»»»

Playgrounds over process.

I stumbled across this little write up:

Playgrounds over Paths

Today’s standard design wisdom focuses on the design of linear paths. Sometimes they may branch, but they’re ultimately a sequential set of steps towards a desired outcome.

Within complex systems, these paths often lack the flexibility to adapt to emergent conditions - users acting outside the “designed boundaries”.

Instead of designing explicit paths, APD is oriented towards the design of playgrounds - limited spaces where the boundaries are defined by the mechanics of the system. Within these playgrounds, desire paths will naturally form based on different factors: cost, convenience, bounded rationality, etc.

In this context they are talking about designing user flows. Advocating for thinking about how users may act in non linear ways.

But I think there is something here relevant to the idea of process too.

In an agency setting, we think a lot about process. But there are some contradictions here. Most would agree that users are non linear. We often tear down the marketing funnel for being inadequate and overly linear in a world of infinite touch points. We think about campaigns as ecosystems rather than sequences.

But we seem incapable of letting go of linear when it comes to internal process.

I am going to think more on the matter, but the question I have in my mind now is “how can the agency “process” be more of a playground rather than a path? How do we set up parameters rather than sequences?

limited spaces where the boundaries are defined by the mechanics of the system. Within these playgrounds, desire paths will naturally form based on different factors: cost, convenience, bounded rationality, etc.

What does this look like when applied to the context of creative planning and development?

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It is incredible how often just writing down what you’re trying to say can help clarify things. If there isn’t a bullet point outline of what you’re trying to say, I promise it will end up convoluted.

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Strategy is about simplicity. But there is an irony in the work that is easy to get caught up in.

In pursuit of simplicity, there is almost always a byproduct of complexity.

When you start to focus on something, all the different ways that one thing could come to life suddenly appear. And suddenly, you are left with the complex task of explaining why the one route is better than the rest – when in truth, more often than not any choice is the right choice so long as it is made.

Justifying simplicity can get complex very quick. And the more reasoning you provide, the more rationale, the more opportunities are created for your audience to get lost along the way, get caught up in the weeds or simply disagree.

If a brand’s positioning was “beans¹” when an agency strategist came on to build a creative brief, they might (read: should”) start by pushing what “beans” means.²

That’s all to say, while it can be tempting to explore all the possible choices, try to start with just stating what the simplest version of something is.

When we say ________,
what we mean is ___________.

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There are only 3 kinds of presentations;

1. The pitch (here’s why we’re special and a mock of an airplane wrapped in brand advertising)

2. The proposal (here are some things we could do)

3. The compromise (ok we heard you and changed as little as possible. please say yes)

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~

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Most Briefs are wrong about something. 

The truth is, most briefs are wrong about something. Not completely wrong, but wrong enough that good creative work requires course corrections along the way.

If you can’t admit this, and deliver a brief anyway, you are doomed to become the hurdle rather than the bridge. 

The best strategists understand that creative development is collaborative strategy development. The brief sets the direction, but the work itself reveals what the strategy really needs to be. 

This makes a lot of strategists uncomfortable. It requires admitting that you don't have all the answers upfront. It means being okay with strategic evolution instead of strategic certainty.

~

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TOOLS and TOYS

STRATSCRAPSlm

In a failed effort to fix my archival blindness, I built a notebooklm notebook with every issues of the newsletter as a source. 49 issues are a source twice, because I uploaded 50, found out that was the limit, deleted one then uploaded a single file with all 192 prior issues in a single file. Computers are dumb.

Anyway, apparently nearly 4 years of writing can be distilled into 4 topics…

https://scrap.cards/

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A big challenge with Strategy is that it –more than any other department– performs in an amphitheater rather than a theater.

You have to play to many audiences at once, and any time you are facing one direction, your back is to someone else.

(note: this reinforces why I like to think of my freelance practice as “forward facing strategy” – I try to work on projects shoulder to shoulder with people rather than treat clients like an audience member. Together, we deliver something to the audience. And if the audience isn’t singular, well, usually those I work with are better equipped to deliver work in an amphitheater than I would be.

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Freelancer 2x2s

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Happy holidays. Likely the last episode before the new year. but hoping to put something fun together for the inaugural 2026 issue.

Remember, if you’ve got a project coming up in 2026 that could use strategy support, you know where to find me1.

WEEKLY MONSTER:

Here is 2025 in fake magazine covers I made for the newsletter.

over n out.

After a year and a half at Day One Agency as a Strategy VP, I am returning to freelance in the new year.

Why?

Because being the only full time fully remote employee is really hard. Not for me specifically but hard for/on everyone.

Because the agency model is increasingly broken and the cracks are starting to show1. Not ideal to pivot back into uncertainty amid the biggest round of layoffs the agency world has ever seen, but I enjoy freelance because it offers what agencies can’t – to be embedded quickly into a problem and given permission to focus on it in its entirety. As a freelance strategy consultant, I am no longer part of a production line, I am a mechanic listening to the engine knock.

And finally, because I enjoy it. I enjoy meeting new teams and digesting new problems. I enjoy the sprint and the deep dive and even the onboarding. This is where I am able to offer the most.

Services2;

• Research & Consulting

• Project Briefing and Creative team partnership

• Comms Planning

• Go To Market Strategy

• Positioning and Messaging

You can read more at alexmorris.co.

With that out of the way, let’s see what I end up putting in here this time around.

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I made a good better version of a project I have been tinkering with for a while… Still not where I’d like it to be, but I wanted to share now rather than wait till it was perfect.

Scrap.cards is a little website that shuffles through random quotes I’ve collected. It’s meant as a digital version of my notecard box. Note that I am tinkering with it constantly at the moment and there may be moments where it goes down. Also, there are meant to be a mix of quotes and images but the images aren’t working at the moment. Coming soon: a submit feature.

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A variation on the user journey, is the user clock;

Read more here, but I like this way of thinking as a variation of journey mapping/day parting.

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Not unrelated to the news up top;

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A big challenge with Strategy is that it –more than any other department– performs in an amphitheater rather than a theater.

You have to play to many audiences at once, and any time you are facing one direction, your back is to someone else.

(note: this reinforces why I like to think of my freelance practice as “forward facing strategy” – I try to work on projects shoulder to shoulder with people rather than treat clients like an audience member. Together, we deliver something to the audience. And if the audience isn’t singular, well, usually those I work with are better equipped to deliver work in an amphitheater than I would be.

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By 2015, for example, eleven criminal convictions had been overturned in United States appellate courts based on prosecutors’ egregious misuses of PowerPoint. One Damn Slide After Another. (I know I’ve shared this link before, can’t remember if I’ve shared the quote)

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The TED talk I want to see.

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Friend of the pod3 Richard Shotton released a new book recently called Hacking the Human mind. Sensationalist title aside, it is a really nice little set of behavioral science references and guidances that likely wont have anything wildly new in it if you are a hard core student of cognitive bias, but even then it’s worth grabbing a copy just for the simplicity of the information, alongside the examples given. You can buy a copy here.

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The Strategist Deliverable Bingo Card

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Kinda like this as a freelancer’s services menu.

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Craigslist would be a cool tool for researching regional differences.

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Another reason the objective perspective of the freelancer is important

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I really do love a good 2x2

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This would be a fun (though likely unnecessarily complex and overly heady) way to think about comms planning

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relevant essay on going back to freelance

WEEKLY4 MONSTER

Made this a while ago, but it’s remained a fav.

Took a bit longer to get this out because there are a few things I wanted to write about, mention, share. But it was holding me up. so here’s some stuff that is more scrap, less strat.

also, no magazine cover art this time because I have to get back to work. ¯\_(ツ)_/¯

a thought;

We often feel that process stifles or dictates the outcome. But the function of a process is the exact opposite. You can either work based on process or outcome. A process is meant to ensure that you don’t land in the same place every time. A process is a formula to be applied, while a defined deliverable is solving for the answer you already have.

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the thing is, reading the article, nothing he says in wrong. But also a huge part of it is the fact that everything is in house. The need for strategy is largely because the creative team isn’t up to speed on the brand or bc the client doesnt have a clear vision of how to show up in the world. Neither is a problem at Liquid death’s in house team.

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Admittedly I know very little about basketball but I made this for some reason.

The abstract is more valuable than the specifics I imagine.

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Corners of the Internet Database. Have I shared this before? cant remember, but worth the risk.

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A slide I made 5 or so years ago:

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Sometimes you look back at notes and accidentally spark an existential crisis.

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Idea vs Execution

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We are often better at critiquing and improving than at starting from scratch.

What if we briefed team in this way?

“Find an ad campaign to use as a starting point, then reconstruct it to fit our objectives. Redress as needed to obscure the original source.”

I have a hunch the average outcome would be overall stronger than the “from scratch” process.

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I love this so much

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“You can be relevant as hell and still be boring as fuck” - Martin Weigel

Relevance might be just as toxic and damaging of a word as insight

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The real cycle of life:

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Deliver a word doc version of the slides. here is what has been decided, what we presented, and what needs to happen coming out.

(a note I took once?)

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The agency approach to most things is a technical-debt production line.

PM Researcher

The Long-Term Consequences of Quick Wins

In my last article, I explored the value of taking a concept from one domain and applying it in another. This practice stretches our thinking and helps us see patterns across systems. Some of the most powerful insights don’t come from inventing something new - it’s from translating an existing idea into a fresh context…

Read more

a year ago · 34 likes · 2 comments · Nicole Williams

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Something I’ve seen a bit of and really like: public work in progress versions of a book. be it google docs or blog posts, there is something really interesting about this.

Less Unstrategic

Tom’ Critchlow’s Creative Independent

I started something similar but havent made any progress since last time I shared. So You Want to Do Some Strategy

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WEEKLY MONSTER

Here is a PDF of some collages I made while living in NY.

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Here are three things that would have saved me a lot of stress if I had seen them at the beginning of the week

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And something I was trying to remember at some other point in the past few weeks.

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STRATSCRAPSlm

In a failed effort to fix my archival blindness, I built a notebooklm notebook with every issues of the newsletter as a source. 49 issues are a source twice, because I uploaded 50, found out that was the limit, deleted one then uploaded a single file with all 192 prior issues in a single file. Computers are dumb.

Anyway, apparently nearly 4 years of writing can be distilled into 4 topics…

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Chronic vs. acute problems

The two should be dealt with very differently.

Acute problems are usually caused by external factors, unforeseen circumstance or an unfortunate misstep. They can’t be prevented but they can be quickly addressed. People use the term “a bandaid solution” – these are the situations when band aids are a logical response.

Chronic problems are a product of behavior. They can be initially triggered by something more acute (change in team, budget, etc) but they become self perpetuating. They can only be solved through rehabilitation. e.g. choosing to do the work needed to change the problem behavior.

Basically, don’t treat metaphorical back aches like metaphorical finger cuts. One requires a change in posture. the other is just a reminder to pay more attention.

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New Are.na channel just dropped. Started as a place to put the theory of what makes advertising work to paper through the lens of advice applicable to different points in the process. It may be evolving into a daily grievance repository. There is overlap to be sure, but it is definitely a reactive collection.

A few excerpts;

• Ads that aren’t entertaining or interesting are an act of violence against the viewer

• Take the time to think about how to best set up internal reviews. Respect everyone’s time

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A while ago, I talked about Fisho Magazine, created by Nick Marzano1.

Well Nick put out the third issue and it is also awesome. Because it is a fishing zine done by a Creative Director so of course I dig it, but additionally because it is also about subculture and the intersections they are formed from.

So even if you don’t like to fish, it prompted some things more relevant to the world this newsletter inhabits;

Nick sent me this linkedin post as a sort of primer for what kinds of things he was thinking about at the moment.

To which I responded with a keynote mockup (that’s my native language)

ALSO, STILL RELEVANT FROM FIRST TIME I TALKED ABOUT FISHOP IN A NEWSLETTER:

1. Niche doesn’t mean small. There is a continuum between mass and insubstantial. Fringe is often more visible than mass because of its contrast.

(really wish I had remembered this before chatting with Laura for Niche ID. on the definition of Niche)

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and I didnt even get to talk about Brian Eno’s new book. 😞

WEEKLY MONSTER

Imagine pulling off the freeway halfway between seattle and portland, in a town where the only lights at night are from a menthol refinery and the McMenamins hotel.

You are hungry and have to pee so you stop at the McMenamins hotel bar. It is 9pm and nobody is there. Then you head to the restroom and discover this:

See, THIS is what should be in our “CULTURE” decks.

and they say art is dead…