Holy locomotive morning!

This nonsensical phrase first pulled into the station of my mind when I lived in New York, perhaps because of so much time spent on the train. It was sometime in 2017 or maybe 2018. For some reason it’s stuck with me since. It has the right sound, propulsive imagery and I’ve come to think of it on certain mornings which feel charged with the right creative momentum and feeling.

On a recent morning in June while in the satori pull of coffee, I captured the image above, of my desk “in motion”. I was experiencing the good kind of writing where phrases like holy locomotive morning find you without your searching and somehow are exactly what you need for some particular paragraph not yet overworked.

A few years back I realized my favorite photos tended to be the ones taken while experiencing particularly joyful emotions and I’ve tried to make a habit of snapping a photo whenever I am experiencing them. The subjects of these kinds of photos are the emotions of the moment more than what the images literally capture.

That image of my desk “mid-flight” became one of the first in my latest collection on Sublime, which is labeled How my next reality feels.

I’ve begun to realize (or perhaps remember) that I am my career. That the way I feel each day, the projects I decide to focus on, and the unique combination of my interests sum up to my career. And a single vocation, role or title is only one contributor to that broader ecosystem I am tending to everyday. There is no better guide to determining what belongs in my ecosystem than how it feels to do a particular thing, work a particular job, or interact with particular people.

I’ve stopped using the simplistic framing of “what do I want to do?” (which is a question for the brain) in exchange for the much more resonant “how do I want my next week, year, or life to feel?” (which is a question for the soul).

From there I simply need to search for and do more of the things that feel the best. Search for the moments that glow and discover what made them so resonant.

Have a great weekend!

Jake

PS - if you love the act of curation, enjoy receiving and sharing great recommendations, and find yourself positively glowing while sitting down in a long morning or stretching afternoon with a stack of interesting reading… you would likely love my project Printernet which I’ve been working on since 2022.

Printernet lets you turn your “read later” list into a personalized magazine, instantly. You can view what other Printernet readers are reading, recommend the best stuff you’re finding to others, and set up a weekly print schedule that will compile a personalized magazine for you each week.

Come join us!

In my best year, I hit 10-12 of these. Given my love for curation and recommendations, these are important to me.

But here we are! Given that this year is already proving to be exceptional with respect to my round up posts, I decided to experiment with the usual formatting of these. Instead of distinct sections (reading, podcasts, projects), everything is intermingled. Take what seems interesting, à-la-carte.

For the future version of myself reading this, these were the months where I

• Went to Rio for my fourth time with Clutch. This was the first time Tessa joined. We had a delightful time exploring together, heading to Ilha Grande and being surrounded by mountains and all that water. Months later, when on Lake Travis, I’d find myself daydreaming about being that far south again and getting teary eyed.

• Went to Paris (for my first time ever), Kate’s wedding, and Switzerland (for the first time ever). I will try to always remember biking around the overlapping streets together, turning out onto the broad views of the Seine as the sun was setting, that odd angry man who ran the bistro we stopped at for dinner who I witnessed punch himself in the face, all those pastries (and that particular breakfast croissant sandwich from Désirée). And remember the wine nights with Luke and Rod, Kate and Remi. Don’t think we could ever forget the Hilma Af Klint exhibit, overwhelming in scale, glowing! Tessa gifted me a Louise Carmen notebook and we customized it in their tiny store together. Months later, I’d sit down to write in it for the first time and a full short story would spring onto the page in a single sitting at Switchyards. And don’t forget the long gorgeous drive to Switzerland, the electric car fiasco and the jovial hacker at Avis, the musical cows like wind chimes, the summertime meandering through the evening streets of Bern, and all the rest.

• Turned 30 and we celebrated 3 years of marriage

Happy summer everyone!

My conversation with Matt Webb is out.

Matt Webb is a writer, inventor, and the creator of Poem/1, a clock that tells the time in AI-composed verse (my very own Poem/1 is sitting on my shelf as I write this, after Matt raised ~100k on the kickstarter).

Matt and I talk about “design pathfinding”, why inventing in the AI era means making things before you fully understand things, and how jokes, demos, and small experiments can reveal unexpectedly serious possibilities. Matt walks through the origins of his app Galactic Compass (an app which simply points to the center of our galaxy at all times) and Poem/1, along with his approach to note-taking, writing, Kickstarter and storytelling strategies, and building a creative practice around curiosity. Matt is exceptional at staying sensitive to the feelings objects evoke and following strange ideas wherever they lead.

You can also check out the first interview of this project with Keegan McNamara of Mythic Computers here.

“Listers”: a bird watching documentary

Watch this indie documentary! Two brothers live in their van for an entire year trying to see or hear as many birds as they can, pursuing what is known in the bird watching world as a “big year”. Why?

1) Quentin was stoned and flipped through a bird book

2) "That's a good way to learn something, trying to do it at the most extreme level"

This is a perfect example of what my favorite docs have in common: an authentic scrappiness regarding the documentation aspects, genuine passion and ambition often about something seemingly mundane or obscure, a cast of oddball characters, plus the bonus of showcasing experts at work. It shares many virtues with my favorite doc of all time, The Parking Lot Movie.

I made myself an experimental app for tracking books I want to read in one place.

It works from basically anywhere on the internet (instagram, goodreads, twitter, iMessage, etc) and each cover links to the original source where I stumbled into it. It is using Google’s free OCR API (1000 images a month are free) to extract title and author too, so it’s clean data + gorgeous covers. I call it “wtr” (pronounced ‘water’), as in “want to read”.

This entire acoustic set from Big Thief is wonderful, amidst a verdant Irish spring.

But I particularly love the last song ‘Space and Time’. This is the song’s marvelous debut according to Pitchfork, though I’ve found plenty of live takes of it from 2024 shows.

I keep a bucket list of shows I haven’t seen yet and Big Thief is at the top of that list. I recently heard in an interview with them the probable secret for why I am so drawn to their live recordings: they view live shows as a different kind of practice, as a way to experiment with their familiar songs. You get the sense that their songs can go anywhere and they often go to entirely new places than the ones on the albums.

How the so-called “attention crisis” may be a “curiosity crisis”.

This fantastic essay from John Paul Brammer, How I learned to read way way more, resonates with how I’ve maintained healthy reading habits in a digital world. John discusses it poetically without becoming too abstract. I think this quote capturing how John stopped fighting his own attention by becoming more playful with his reading sums up the spirit nicely:

“I had to cooperate with the zigzag”

I redesigned my website

My site got a whole lot simpler. The 2024 → 2025 era of the site was defined by an early 2000s interactivity and could generally be called sprawling. It had digital gardens, a page with the best cup of coffee I’d had recently, marquee scrolling text, and other fun stuff like that. But in 2026, I felt a pull towards simplicity.

Introducing, the Dumbish Phone

Tessa and I have discussed replacing our iPhones (like everyone) for a long time. I actually thought about starting a company that was basically what Light Phone has become back when I lived in New York in 2017… We’ve thought about buying one of the many “dumb phone” options like the Light Phone, Meadow or even tinyPod which turns your Apple Watch into a delightful iPod style “phone”.

We’ve thought about buying simple flip phones and we’ve considered getting rid of cellphones altogether, but have never taken any concrete steps to try and add constraints and friction to our phones.

But this past week, Tessa did some hacking with her iPhone to make it a shell of its former self and I quickly copied her. The north star was to try and make it more like an eReader. We’ve both now switched our phones to black and white, removed all of the apps that lead to doom scrolling, leveraged Apple’s native “focus” filters to limit which sites and apps and contacts can reach us and be reached, and added screen covers which make our phones feel like eInk. It’s been a pretty good experience so far, here is what our phones looks like now.

Here are the apps I’ve kept on mine (in addition to the obvious ones like Messages, Maps, Notes, etc): Pocket, Printernet, Soft, Brick, Podcasts, Spotify, and ChatGPT.

10 rules for students and teachers, from John Cage

Some things which stood out to me: consider everything an experiment, find someone wise or smart and follow them, the only rule is to work as work will always lead to something, separate the creative self from the editor self, enjoy yourself, read everything you can.

Faith in eventually

An old gem I recently discovered from the designer Jason Fried about trusting that you’ll get there. On its face, this short blog post is about pursuing a new product or design, but of course, it’s really about trying to do anything meaningful and difficult.

Ending the round up with a request

I am on the hunt for more wonderful documentaries and have wanted to find one which follows a professional novelist from the start of a new novel to the publication of the novel for a while now. Does anyone know of something up this alley? The LLMs suggested two which I plan to check out: 'Scribbling: A.S. Byatt' and 'Imagine: Ian Rankin and the Case of the Disappearing Detective'

That’s all for this summer roundup!

Remember: blessed are the curators! Consume wonderful writing, videos, interviews and the like with the magic of the internet, but don’t forget to do your part to help others find the good stuff <3

Jake

You have to surround yourself with work that expands your sense of what can be done on the page. Otherwise, you risk shrinking back into the comfortable familiar room of your own limitations. The room with the ordinary words, overused and overburdened, with the same structures and ideas you’ve been overworking for years. There is no experimentation and no hope for reinvention or renewal there.

There is an image in my head of my own creative capabilities, expanding out and contracting again, like lungs filling with air, pushing against the walls of the room where I write. By staying in the work, which involves pushing further and hunting for inspiration, I keep stretching the edges of my own abilities. The room you write from seems somehow bigger, the possibilities more vast.

Surrounding yourself with excellent writing stops you from regressing to the quick shallow inhalations that are so much easier than those deep sustaining breaths you are actually capable of. I can easily write sentences lazily, with half my attention, and have them dressed up and looking nice. But that won’t do. It’s like a beautiful looking meal made of gelatin1.

When my older brother and I were little, we’d visit our grandparents over Christmas holidays and sit on the Persian rug of their living room to play with legos. My parents would haul these massive bins full of them down from the attic. Once we had them, we’d spill them out over the rug, with all those wonderful colors. Then, we’d hover our noses inches above the lumpy plastic sea and begin to scan. We were searching for the best pieces, which you’d only know when you saw them.

I have to push further, spend more time picking through words and ideas like sifting through the legos, until I uncover the perfect one that clicks into place. The threat to this most days, is impatience which is really just tolerance for “good enough”.

On evaluating the work in progress: under the influence

The temptation to do so cannot be overstated, but I must resist the invitation to fall in love with my own reflection on the page.

I must also resist the opposite affliction, the nausea of consistently falling short of my own ambition week after week. While walking out into the air, it’s usually a bad idea to look down.

These twin hazards are always present. In the ecstatic aftermath of writing 2,000 words effortlessly I quietly wonder if I am writing the perfect novel. Then morning comes. I open my computer and begin to read yesterday’s work. What was surely glowing is now dull and scratched up. How could this be? What has happened to the expertly handled ideas I so deftly summoned? They’ve rotted overnight. A third grader tip-toed in and began banging on the keyboard, surely these banal cliches are not my own? Everything is lost.

Ian McEwan says that if you are unhappy with the last paragraph, the entire piece might turn to ash.

But if you are pleased by the last paragraph, everything else “springs back into life”.

The threat is always delusion, for better or for worse. Yet the threat can only be recognized and wrestled with, it cannot be cast out because we are unable to be objective as both the creator and audience-of-one for our works in progress. I am finding it better to reach for the analogy of drugs. Working on a large creative work is like ingesting a drug. You will see and think things that are not real. Those mirages are not enemies per se; the enemy is forgetting. Forgetting that you are under the influence. You must remember that your nightmares and ecstatic dreams are both fictions.

On saving the “good stuff”

Give your current work everything you have. Do not risk hoarding a part of your genius for some future dream.

“The temptation to save something for a future piece is a signal to use it now”

This is perhaps the single thing from The Writing Life that has ascended from mere advice to a mantra for me. Everything, nearly everything, can be folded in. The resulting richness, dissonance, and complexity is worth the effort.

And then for the old blade grinder which is good enough, which has stepped into the broken Encore burr grinder’s place without fuss and has done its best. Isn’t it refreshing to do things simply? To come back to something small which is so reliable?

I couldn’t omit my favorite mugs either, there are many. Each one has a way of almost glowing there on the shelf when its day has come. I am happy that there is a part of me, an inner voice which is unserious, that ritualizes little choices like these.

And finally to Michael Nau, and Tangle’s Way, overbrimming with soft longing that is somehow propulsive, rather than stuck. Which I recognize in myself too as I drink my third cup of outstanding coffee.

But here is what I am wondering…

Even when AI can produce a record that sounds like a Brian Eno record, working with Brian Eno is way cooler.

So the whole idiosyncratic process of working with an expert will still be highly valued. Even with identical artifacts (the ultimate output)1. Because one output of the creative process is how it actually felt making the others. That might even be the most critical one. In this vision of the future, proximity to those great at conducting creative processes becomes more important than the final result of those processes. The value comes from proximity to judgment, experimentation, and to refined sensibilities.

For amateurs (positive) and DIYers, of course the AI substitute with the same end result will make more sense most of the time. The average Bandcamp musician cannot work with Rick Rubin, or Brian Eno, or Jack Antonoff and will happily accept the “knock off” artifact which is cheap and instant. But long term, the best artists will still aspire to the real thing, the deeper experiences that arise from working directly with experts. At least for the experts who have a lot of interaction and exchange with their clients.

The same is true for website developers, industrial designers, interior designers, architects, graphic designers, and coaches. And this won’t only apply to the household names in a given field - I think there will be sufficient demand for this sort of collaborative experience to keep thoughtful experts from the “permanent underclass”.

So maybe AI will “merely” raise the floor for creative work, rather than smooshing everything against the same ceiling. Maybe the facsimiles will make the marginal song, or coffee shop interior, or CPG package, or website way more beautiful than they are today, while simultaneously making the value of working with expert humans even greater. Maybe differentiation will still exist even when there is no observable difference between an LLM replica and the real deal. Maybe the way to thrive as an artist in the future is to be a very pleasant, insightful, and available teacher - one who brings their collaborators or clients along for the ride.

Maybe.

Sula vie dilejo,

Jake

If you want to untangle something, like string or a cord, focus on adding as much “looseness” as you can rather than trying to untangle it.

The shift in focus from the outcome (untangling the cord) to the means by which the outcome is achieved (more loosening) works surprisingly well.

Of course, as must be the case for the wisest sages, Kevin’s advice is often more broadly applicable. You can think of untangling a complicated situation, or a tense conversation (notice the adjective… tense).

But I recently thought of applying it to a different scenario, a new scenario, while thinking about someone close to me struggling with their current day to day reality and feeling anxious about finding the right next move.

I’ve been in similar frames of mind before. You somehow find yourself in a daily reality you despise, yet you feel obligated to continue because of real life responsibilities. Like paying rent, having student loans, or having seven months left on your lease. Sometimes, you even feel embarrassed by the idea of abandoning the prestige or status associated with your current situation (a good job in a respected industry, a specific college degree, or even where you want to live). Whatever the specific tensions of the present moment, you feel generally overwhelmed and even hopeless.

This frame of mind often leads to wanting to do something immediate and extreme: quit the job tomorrow, stop talking to a person altogether, or drop out of school. These can sometimes be the best paths forward, but they are often analogous to tugging at the tangled ball of cord in anger and tightening the whole mess. In these types of situation I think that what has normally happened is your sense of options has collapsed and your sense of self has fused to your current reality.

What has worked for me in situations like these is to focus on adding looseness. In this context, looseness is about expanding your sense of what’s possible. The tension comes from feeling trapped or stuck in your current reality and understandably the impulse is then to punch a hole in your current reality and get unstuck. But what actually loosens that constrained feeling is naming the countless options available to me that don’t involve the limited drastic actions.

To do this, I turn to a dependable friend: questions.

exploring the source

• What is the source of my suffering?

• Are there ways to remove the source without abandoning the whole reality? Could the source be hiding behind the current reality?

• If I do decide to abandon the current reality, how can I be sure I don’t replace it with a reality which possesses the same source of suffering?

• When was I last happy with my daily reality? When did it change to suffering or feeling like it does now?

• Are there other, non-obvious contributors to the problem I think is the main problem? Could one of those contributors actually be the main problem?

reconnecting with yourself

• If negative feelings hold valuable signals about the kinds of things I love, what secrets are these negative feelings holding?

• What are 5 to 10 things I am absolutely certain I enjoy doing? Can I do one of them today, tomorrow or this week? Could I make a habit of doing at least one of them until I am out of my current reality?

• What are indirect small changes I could make this week to make me feel more grounded and like myself?

expanding the timeline and uncoupling yourself from your current reality

• Have I felt this way before?

• What did I do last time I felt this way and would I give my past self any advice in hindsight?

• When I fast forward ten years from now, does the current suffering feel smaller?

• If I were giving advice to someone I love who was in my current situation, what would I tell them?

• If 3-5 of the people I consider wise or admire greatly were my personal advisors, what would they likely tell me right now?

alternative paths and sense of scale

• How many alternate paths can I think of this morning on my walk?

• Of all the options I come up with, how many will still be options in a week or month?

• What is the smallest version of the most exciting alternate path and could I experiment with doing it very soon?

• What’s the exact opposite of my current reality?

• What are the parts of my current reality that feel most aligned with my true self?

• What are variations of my current reality that feel exciting still?

• If the binary extremes are off limits (quitting vs staying, dropping out vs status quo, etc), what alternatives are most compelling? Which variables feel like they offer the most relief?

• What’s a bold but reasonable request I can make to the relevant person or people contributing to my suffering that may lessen it?

hatching the private plan and creating pockets of your new reality

• Let’s imagine I’ve already changed my daily reality (by quitting, dropping out, moving, etc)… what would I do tomorrow? How could I set myself up to make entering my next reality smoother?

• If I had to make the construction of my next reality a secret project I work on privately over the next month, what would my plan be?

• What are a few things I’d love my next reality to include?

• Who has a daily reality that I admire? What is it about that reality that I might be missing in mine?

• What work am I most proud of? Is there a way to do more of that kind of work in my current reality? If not, can I do that type of work without my current reality’s permission?

• Is there a small activity, project, or ritual I can introduce that will make me feel more aligned with my true self and the reality I wish I was in?

• What does the version of me in my aspirational reality do every day? What does that version of me feel like? Can I begin one of those routines, habits, or feelings now?

• Are there any frames of mind that make me immune to the suffering of my current reality? What makes those frames of mind possible?

• How can I make my current reality feel lighter or more playful knowing that it won’t be my current reality for much longer?

Keep expanding your sense of what’s possible by excavating more questions. You will know when a specific question feels more energetic or resonant for you than the others. Focus on that one until you have some answers you think are true.

Go on a walk every morning and make it your goal to discover at least one new question which makes you feel slightly lighter, more optimistic, or curious. Write about the tension you feel — state the facts like a military report, but also ask yourself questions and answer them directly. Resist abstraction.

Cut your time online in half. Make sure you get outside more, are eating well, and sleep on a consistent schedule.

You do not need to solve every problem. You do not need to find your life’s work or the perfect path within the next few months. Think about stabilizing yourself within your current reality before you attempt to transform it. Enter your new reality calmly, confidently and with intention.

The trick is to shift your focus from getting out of your current situation and instead look for the possibilities that feel most inviting. Those are the doors to your next reality worth walking through. It is almost always better to change your reality by being attracted towards something than it is by being repelled from something.

Know that the people you admire have been exactly where you are now. There is no need for shame, embarrassment, or regret. This reality is a lesson, teaching you which realities are not for you and which are.

You know your current reality is officially temporary. You know a new reality is forming. Breathe, talk to people you love, be patient and live in your current reality a little while longer with the trickster joy of knowing something it doesn’t: it’ll soon be gone.

Why?

Being prolific ensures you get better over time. Whatever it is you want to spend your life working on, it’s almost certainly true that you will need to be good at it in order to succeed at making a living from it1. And the best way to get good at something is to do it a lot more than the average person. There are, of course, other key ingredients to improvement (like analyzing your gaps, coaching from people already world class at it, etc) — but none of it matters if you don’t do the thing a ton. There is a clear corollary to this too: you should focus your energy on something that feels effortless to spend an obsessive amount of time on. This allows you to actually be prolific at it.

Why else is being prolific good general advice? Being prolific in the way I mean it requires finishing things. Writing a ton of half-finished (and abandoned) short stories or essays will limit your improvement. You end up just getting better at starting new stories or essays. Not finishing great ones. It is crucial to finish things because it allows you to see your own progress over time (and learn from your past work), find an audience, get feedback from the world, and go from amateur to pro (in the Steven Pressfield sense). This was part of the value to my “30 Days of Creative Programming” project and how I’ve shifted to thinking about rotating my interests in larger, modular “chunks” throughout the year.

It also seems that for most fields and most people who eventually succeed, things take time (more on dealing with that soon). It is rare to succeed from your first piece of work. So being prolific evens the odds and corrects for the randomness of the world (what’s popular at a given time, the right person seeing something, etc).

Ok, so that is the value of being prolific. But is that enough?

No, I don’t think it is. I think in order to be prolific, you have to be patient.

This is because being patient ensures you don’t lose hope and quit, which would thereby break the “be prolific” rule. Orienting around the idea that “your life’s work will take a ton of time” removes a lot of the anxiety, urgency, burn out, and bad decision making that can accompany those things. In other words, this “patience orientation” ensures the work stays light and playful, or as Graham Duncan puts it, keeps your grip “loose”.

It’s not just that patience helps you be more prolific though, the reverse is also true. Being prolific has a positive effect on being patient: having a ton of finished work that improves over time will help you “keep the faith” through tough times and prevents you from getting antsy. You’ll have your body of work, proof you are getting better and producing things you are proud of. This is the stop gap against idle daydreaming, thinking everything will work out for you without the accompanying required action. That really matters to having the persistence and longterm view required to succeed in a sustainable, career-long way. You want delicate tension between urgency to ship better things over time and the patience to keep going without rushing the work.

This is like the advice I first saw articulated so well by Visa and have taken on as a sort of mantra ever since: so much of success is actually just about managing your own psychology effectively. You have to stop your inner critic, the comparison demons, the fear of missing out, short term distractions, creeping despondence or the urge to pivot. Those who can do this are able to keep pursuing their life’s work and therefore are more likely to succeed over a long enough time period.

There are three possible exceptions to this guidance: the one hit wonders, the slow and low craftsman, and the lottery winners2. In each of of these groups, we see either hidden work which counts as being prolific or luck which I don’t think anyone should aspire to replicate as a strategy.

It’s your life’s work, it’s supposed to take time and be difficult. Good luck (to you and me both).

It induces the initial reaction to the work.

It compresses the key idea of the work, maybe even compresses it so much that it only contains the essential “interesting” impression of a much more complex whole.

An inability to write good titles, which occasionally a famous author or musician will confess to, suggests some deficiency with understanding. Either an inability to understand what is most compelling about the thing we’ve created, or what is most important, or how to bottle it in a handful of words, or what other cultural cousins our work is related to. If the creator can’t name the work, do they really understand it? The deficiency may simply be a skill deficiency, but it could also be a deficiency in patience, motivation, or effort since finding good titles can often be so tricky.

In the Internet Age, we’ve all come to internalize the value of a good title on some level. Clickbait is a household name. But if you wonder about good titles more deeply, not seeing them as a cheap trick optimizing for cheap attention (a click), but something more meaningful, they can begin to reveal mysterious power.

There is great power in naming things well. It’s there in Genesis, in folklore, in marketing. The power is not just in captivation or attention (the trick), it’s about legibility and finding the right audience. A good title is almost like a good password, the right one will get through to the right people.

A fun little game Tessa and I play occasionally involves one of us thinking of a business idea, app, or invention. Then we spend a day or two trying to think of the perfect name for this hypothetical project. Once we find the right name, the game is over and we don’t feel any other pressure to actually pursue the idea. On the other hand, whenever I have a new seed of an exciting idea for a creative project, finding a good name can be what pushes the idea out of the Notes app and into a word processor, code editor, or the real world. In both cases, there is finality and something undeniable about a good name.

Titles are so powerful that I sometimes think of one before having written something and the title itself is sufficient to provoke the writing it will eventually headline. In fact, that is precisely what happened here.

I am always on the look out for people who ask good questions, maybe I should start keeping a list of people good at naming things. If you know of any, send them my way!

Here are some good titles I’ve come across recently:

• My Year of Tech and Relaxation

• You are what you choose

• I give you feedback on your blog post draft but you don’t send it to me

• The Case That A.I. Is Thinking

• What’s Going On Here, With This Human?

• Willingness to Look Stupid

• Objects are losing their innocence

• On Being Interested in Stuff Almost No One Is Interested In

• AGI is here (and I feel fine)

• Do We Need New Ideas, or Better Influencers?

• The Same Damned Thing Over and Over

• Questions to ask your friends

• Toward a Shallower Future

• Metaphors We Compute By

In general, 2025 was far more creatively focused (and quiet) than my previous 3 to 4 years. Before last year, I went through a period of rapid creative exploration and experimentation, which was delightful but exhausting.

A rising sense that I ought to get serious about focusing and prioritizing on one or two core projects finally settled with clarity at the start of 2025. My year was therefore more calm, deliberate, and surprisingly, my need to be online or share updates waned to almost nothing. However, I kept writing and working. It was just that I felt less anxious to get things “out the door”.

I am writing this in a single sitting because it’s been too long since I’ve been able to sit down and write something that actually gets out of my office and onto the web. Sometimes short and sweet is a nice way to break up those long and meticulous posts. I have five or six posts that have been in progress for multiple months. I am excited to share them but they are longer and need more care, so they’re also burning a whole in my drafts folder.

Here is what’s coming:

• good_work episode 2: check out episode one with Keegan McNamara in the meantime.

• Coolest folks I discovered in 2025: a simple list of interesting people I discovered last year. You can read the 2022, 2023 and 2024’s lists if you’re curious or looking for new follows. I am sure each person on them is still very cool.

• Marking Your Year Between the Pages of the Books You Read: a new project I’ve made with a friend that is in the Printernet universe and launching soon. This was inspired by a wonderful, personalized Christmas gift I received this year!

• An essay about boredom: this is the piece in the group which has been in my drafts the longest… going on 2 years now I think. It has a lot I am very proud of and therefore being too precious about. There is still some trimmable fat.

• Books I Read in 2025: exactly what is sounds like… mostly for me / record keeping purposes but others might see something that looks interesting!

• Rough Draft 2026: a loose review of 2025 and a looser plan for 2026, following the signal of those things that energize me most. You can check out some old rough drafts or read about the general idea if you’re curious how they work.

• The Writing Life: a short post about some experiences I’ve had while working on a longer work of fiction. One of those “notes on creativity” types of posts, inspired by reading Annie Dillard’s book of the same name.

• Your Books Deserve To Be Read: another new project I’ve made in the Printernet universe that will be launching soon

The name of this newsletter and it’s predecessor site is Polymathematics. It’s a term I coined to describe the practice of multiple interests over time. I think I used to ignore the “over time” part and as a consequence would get anxious about not doing everything all at once. Since late 2024 and all of last year, I think I’ve accepted the true nature of a creative life revolving around more than one interest. The true nature should be slow, calm, and happy to let things brew (even for years). Lots brewing, more to come!

Talk soon,

Jake

Why did I pick that? Truthfully, I cannot remember the exact reason. Rather, there was a gestalt of swirling associations with the phrase, and some have seemed like the real reasons over time.

The first and most straight forward is an idea echoed by Macbeth1:

Tomorrow, and tomorrow, and tomorrow
Creeps in this petty pace from day to day
To the last syllable of recorded time;
And all our yesterdays have lighted fools
The way to dusty death. Out, out, brief candle,
Life’s but a walking shadow, a poor player
That struts and frets his hour upon the stage
And then is heard no more. It is a tale
Told by an idiot, full of sound and fury
Signifying nothing.

It’s the idea that all of our writing, and indeed our lives, will at best turn to footnotes in grander or more timely narratives. In this way, it’s a slightly more personal version of “memento mori”, a reminder to myself to not be too self-important or consumed by the day to day drama of everyday life.

The second idea is almost the opposite to the first, a reminder to exalt the footnotes. It’s actually an elevation of footnotes. The footnotes and side trails are often the most interesting. Just as the side conversations, detours, and under explored areas in life can be the most interesting too. Some footnotes are conversational and simple asides which did not fit into the main text naturally, but others are the core ideas that informed the main piece or open the aperture of how a work was created2, letting you peek into the office of the writer. They are escape pods out of a restricted format, standardized phrasing, and the facade of the objective creator into the real world of connected ideas, natural language, and often humor3. So from this angle, the phrase means only the footnotes really matter.

Footnotes are often where the formal voice yields to the conversational and authentic voice of the writer. It’s where unadorned genuine interest takes over. This is the same reason I love parentheticals, what is meant to be an optional half-related idea can often turn out to be a portal to new rich ideas. Footnotes and parentheticals often represent a conversation the writer, or text, is having with themselves. I like that meta bend.

Finally, footnotes feel appropriate for the internet era and twitter, as they are sort of the predecessors to the hyperlink4 and the self-aware vanity of the internet driven media environment we now find ourselves in. Everything is commentary on commentary, threads and replies to replies, context about context, and self-referential.

Ultimately, what we expect to be our most important work often isn’t. And what we consider small and unremarkable footnotes to our own lives or work might turn out to be the most interesting parts.

So, it’s only footnotes. Or, if you like, it’s only footnotes.

“One of the first things I ask people is “what have you tried?” Would you be surprised to learn that most have tried nothing?”

What a delightfully clarifying question. What have you tried? And then a simple truth, that most of us barely try. Yet again I am reminded that the obvious is often overlooked.

It strikes me how easily one can trick oneself into being despondent about a goal or life pursuit when in reality one hasn’t even tried to succeed. It is very easy to equate “effort exerted” with legitimate attempts at succeeding. And then losing hope having done a lot of the former with little of the latter.

Indeed this has happened to me more than once. With the first version of the Printernet app, I realized months after abandoning it that I was mentally considering it a failure. It wasn’t until I sat down and wrote about that experience that I exposed the fact to myself that I literally never launched it. I shared it with a handful of friends, but that’s it. And yet I’d mentally filed it away as a failed project.

I worked very hard on it, encountered and solved many problems - yet eventually I found myself unsatisfied with the app and abandoned it. Only later did I realize that the failure was not the project, the failure was giving up on the project I still believed in, not giving it a chance to succeed.

The other example where this strange self-deception has happened is with my fiction writing. I often find myself overwhelmed about not “succeeding”, but I have only submitted or shared 2 or 3 pieces of fiction with editors, readers, etc. And one of the times I did submit a short story to a literary magazine, it was indeed published and made available in Barnes & Noble nationwide!

In both of these examples, I exerted a ton of effort and took them very seriously. I spent months programming the first Printernet app. I wrote 15+ short stories in a period of a few months. But these things aren’t even close to being equal to “trying to make them succeed”. Hard work is merely the first step. Hard work is table stakes (necessary but not sufficient, you know the drill).

Giving your work a chance to succeed, actually trying things, is entirely distinct from the effort exerted on it.

This is a question Keegan McNamara has had in mind since roaming around the “Arms and Armor” exhibit at the MET over three years ago.

Keegan wanted a computer as beautiful as the 19th century firearms on display at the MET. A piece of technology that was in many ways, a counterweight to the seamless industrial aluminium and glass that Apple has made so pervasive.

So he built one himself, by hand. He started with clay, made dozens of scale prototypes, carved the wooden bodies of those first versions, hacked together the hardware needed, and wrote the software for the first Mythic computer. The result was a fully functional, intentionally simple, ornate machine as beautiful as the firearms Tiffany & Co. would design in the 1800s.

Many people saw that first machine and thought it beautiful and as a result Keegan now works full time building custom personal computers from his studio in Ojai California. How wonderful is that? For a person who finds it easier to relate to a luthier than an entrepreneur, it’s pretty great.

Keegan and I first spoke nearly two years ago, when I was beginning to sketch out a project I’d been mulling over even longer. The idea was to meet and talk with independent designers, programmers, and inventors like Keegan who are doing good, novel work in pursuit of their own creative vision. People who aren’t necessarily backed by VC money or building another B2B SaaS app, who are removed from the “scenesters” and Twitter hype cycles, and are navigating the difficult and rewarding process of trying to do good work for a living. I’ve spoken to brilliant industrial designers, engineers, interaction designers and programmers, and independent publishers.

Keegan embodies this type of person and I am proud to present our conversation as the first in a series of seven that will make up “season one” of good work, a podcast project focused on people doing the “good kind of work”, rather than the other kind which is far more common and a lot less fun.

You can listen to the first explorative conversation, with Keegan McNamara, below.

If you want to go deep on Keegan’s work, here are a few trailheads I’d recommend:

• Get your own Mythic Computer

• Keegan’s 2025 Config Talk

• Keegan interviewed by The Verge

• Keegan interviewed by The Free Press

• Follow Keegan on Twitter

• A mysterious sidewalk is an invitation.

• The invitation is accepted. Investigative tools are acquired: a laptop and a fresh cup of coffee.

• Answers are found collecting dust on Municipal Servers. We time travel to 1972.

Part One: A Municipal Mystery (Or, Looking For Cracked Doors)

We’ve a new spot for late night vegan burgers and wings in Austin, Texas. It’s a food truck called Nom Burger in East Austin. Last week while walking there from Coldtowne theater after catching a comedy show, I noticed the sidewalk beneath me was signed…

I snapped the photo above, briefly wondered who Terry Edwards was (or is), and soon my curiosity was eclipsed by my excitement for vegan wings.

Over the last few years, I’ve been trying to notice the “cracked doors” around me. Those little invitations into unexplored facts, mysteries, or simple history. It’s this impulse that made me notice, and photograph, the signed sidewalk that night. Perhaps this was a bit of careful graffiti, politely pressed into wet cement by a tagger named Terry. Or maybe the truth was stranger or more interesting. Maybe this was the first clue that might lead me to uncover a secret society, very much active in the year 2025, creating false histories for unknown aims…

Whatever the answer was, the signed sidewalk was certainly a cracked door and I intended to walk through it.

This week I did walk through. Armed with my laptop and a full cup of coffee in the early morning hours, I began my investigation to answer the question “who is Terry Edwards, and why did he sign the sidewalk in Austin, Texas in 1972?”

To begin, I did what any investigator might: I just googled for Terry Edwards. This is who I found:

Could this be the guy? A renowned flugelhorn player and musician known for his collaborations with David Bowie, Spiritualized, Nick Cave and many other famous artists?

I wondered why a 12 year old music protege from England was in Austin, Texas in 1972. A quick scan of wikipedia confirmed my suspicion that this was simply another Terry Edwards, a fun detour and new tune, but not my Terry.

***

I resumed my search, this time adding “1972” at the end of it.

And eureka! The first result was a link to Austin Gov’s official website, austin.gov1. I opened it up and was delighted to discover a 25 page PDF of scanned meeting minutes pounded out on a typewriter from some long gone summer when the Austin City Council convened.

Part Two: Where We’re Going We Don’t Need Roads (A minor detour back to the year 1972)

Before diving into the Minutes of the City Council meeting held within the Council Chambers of City Hall, let’s set the scene by exploring what was going on in 1972.

Firstly, it was a leap year. And depending on who’s counting, it was the longest year ever…

“Within the context of Coordinated Universal Time (UTC) it was the longest year ever, as two leap seconds were added during this 366-day year, an event which has not since been repeated.”

I’ve been down the road of trying to truly wrap my head around leap years, the Gregorian calendar, and all that jazz. I don’t feel like going back there today.

What else happened in 1972?

The Blue Marble photo was taken by the Apollo 17 crew. This was the final Apollo Mission and the final manned Moon landing ever. Sad.

Other noteworthy events of the longest year in history: a summer olympics in Munich remembered for a terrorist attack, the Vietnam war in full swing, the first commercial home video game console is released, the Watergate scandal begins in June, Nixon beats McGovern in November (a 19 year old Jake will eventually buy a lingering McGovern Campaign pin decades later in an antique store), environmentalism is gaining traction with the Clean Water Act and growing support for the EPA, Title IX became law prohibiting sex-based discrimination in federally funding schools, David Bowie releases The Rise and Fall of Ziggy Stardust and Neil Young releases Harvest. I will eventually fall in love with both of these records in my high school years.

Ok, vibe set, now back to the year 2025 where I am in my office with a half cup of coffee. I have just found the meeting minutes of an Austin City Council meeting from September 1972, which I am hopeful contain the secrets about Terry Edwards, a name imprinted into a sidewalk square in East Austin.

Part Three: Reconstructing History (Or, Terry Unmasked

I begin to read the meeting minutes, searching for my friend Terry.

On page four, I find him.

And he… was a construction company. And what’s more, he was unanimously awarded an $81,000 city contract to build sidewalks in East Austin. Terry Edwards was not an individual defacing public property, no, Terry Edwards was a business signing their work.

But now I had another question.. because the meeting minutes recorded the date as September 14th, 1972 but Terry’s sidewalk signature is clearly marked June 1972. Did Terry’s company ask for forgiveness instead of asking for permission to pave? Could this be a sidewalk scandal which occurred in the same month as the Watergate break in (possibly even the same day)? Might I have discovered a man with a time machine using his invention not to stop WWII or visit Cleopatra, but to deliver on his construction projects well ahead of schedule? Surely not.

I went searching for an answer and quickly found it, buried again in a twenty-something page PDF hosted on Austin City Government servers. This time, we eavesdrop on our favorite City Council in January 1972. Six months before the sidewalk I walked over was signed, and nine months before the $81,000 contract was awarded to Terry and co.

In this January meeting all of our favorite council members are present, with the exception of the honorable Councilman Lebermann2 who, we are told by Mayor Roy Butler, is running late again.

Shortly after the meeting begins — wait… someone opens the door and enters the chamber.

Ah! Councilman Lebermann, now that you are here we can begin.

On page 4 (yet again), it is recorded that the Austin City Council awarded Terry and his team another contract for sidewalk development, this time for $72,000. Here, finally, is the answer to the mundane municipal mystery of Terry Edwards, June 1972. The initial award was given in January 1972, the sidewalk was built and signed in June, and a second award was given to Terry in September 1972 (I’ve yet to stumble on the resulting sidewalks from that second award).

A few other “fun” facts:

• The initial award was given the same month as the sinking of the RMS Queen Elizabeth in Hong Kong Harbor, which was in the process of being converted to a floating university! This was to be used for the “Semester at Sea” program, which is still running today.3

  

  

• The meeting was also the exact day that President Zulfikar Ali Bhutto announced that Pakistan would immediately begin a nuclear weapons program.

• …it was also my grandmother’s 33rd birthday.

• and my uncle’s eighth.

Amidst the excitement of solving the sidewalk mystery I’d stumbled on, I searched for the answer to one last question: Where was Terry Edwards Construction now?

It’s with a saddened spirit that I report, they have since folded.

Part Four: Source Material (The Virtue of Old Media)

I’ve been fascinated with source material lately, which is a romantic way of saying I’ve been reading media from the 60s and 70s (more on that in the future). I’d forgotten just how much of a time capsule primary sources are: essays, journals, notes, and archives really do transport you back. It’s easy to read summaries and overviews of minor and major histories (and will be increasingly easy with AI helping compress decades into sentences), but I am reminded lately that nothing beats the visceral feeling of convening directly with source material.

It’s been a truly magical, almost surreal feeling reading essays and personal letters from the past. Each evening over the past week or so, I’ve sat down with my old magazines (low light and low music to set the mood) and traveled back in time to listen to dead or dying Americans share their ideas, fears, and predictions about their future and the future of their country. Sometimes their concerns or preoccupations seem myopic and turned out to be largely irrelevant, other times it feels like we almost solved large and pressing challenges that still dominate our collective psyche today. But I think part of the charm of wandering in the past is that in either case, some sort of meaningful mark remains in the present, whether left from a Presidential resignation forking reality or a simple name carved in a sidewalk.

Part Five: A Great Place to Exit the Ride

That was fun!

This small little sidewalk research project led me straight to more of these magic time capsule feelings. While largely inconsequential, I find exploring these “cracked doors” to be extremely worthwhile in and of themselves, especially when they are directly tied to the place you live or things you spend a lot of time with. It’s sort of like training your brain to notice the “side alleys”, those winking question marks hidden in plain sight all around us. I like to practice being curious.

Forevermore, when I walk the sidewalks of East Austin and see the name Terry Edwards, I’ll know exactly how it got there.

Earlier this year I got invited to chat with Sam, who hosts an incredible podcast called Inventory-ing. Sam explores all kinds of fascinating concepts “that delve into the lesser-known subcultures thriving in the quiet corners of the internet.”

He’s chatted with exceptional folks like Spencer Chang and Kristoffer Tjalve among others. I am delighted to be in such good company and really enjoyed my early morning chat with Sam!

Thanks,

Jake

Polymathematics is a blog and newsletter about trying to do many things well. Creative people in tech or practical people in creative fields tend to enjoy it most.

Every month I send a post with the best podcast episodes, reading, and coolest people and projects I discovered that month. My recommendations / curations have been applauded by very cool people such as Ted Gioia, Patrick O’Shaughnessy, Harley Finkelstein (Shopify) and more… which is awesome!

If you enjoy this post, I’d love if you subscribed or forwarded it to a friend you think might like it. Thanks!

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Howdy! Each month I post a roundup post like this one sharing the best reading, podcasts, projects, and people or projects I’ve discovered from my month. This is the first one of 2025.

Podcasts

1.) Graham Duncan, Invest Like the Best with Patrick O’Shaughnessy

A recent one I enjoyed where about 70% of the concepts discussed wired new neuron pathways and the other 30% felt like a foreign language to me. Strong worldview held with a “loose grip”. Particularly Grahams ideas about “source” were fascinating to me.

2.) How an Anonymous Researcher Predicted AI's Trajectory, Dwarkesh Patel + Gwern

Drarkesh continues to excel, but the inteview with Gwern really stood out of the recent batch of interviews from him. Gwern has that charming quality of being a world within himself (themselves?) and this interview lets you into that world, introducing new patterns of thought and approaches to work.

3.) Scripts for difficult conversations, Lenny’s Podcast

Tactical and prescriptive conversation with Alisa Cohn about how to have difficult conversations and give constructive feedback at work.

4.) Kurt Vile Interview, Aquarium Drunkard Transmissions

Kurt seems to approach his music with that perfect balance of seriousness and playfulness. Been binging Aquarium Drunkard interviews lately, feels like a cozy radio show of a bygone era.

5.) Jeff Tweedy, Reverb interview

Jeff is always a great conversationalist but something about this Reverb interview feels so light and casual, full of humor and off the cuff. Really enjoyed it, complete with the off camera looks and side convos.

Reading

1.) How to Write One Song, Jeff Tweedy

This is a short little book about Jeff’s experience and advice on songwriting tips, written under the guise of explaining how to write your first song. But of course, this has tons of useful bits even if you’ve written hundreds.

Tip I will pass on for other musicians: grab a random book off your bookshelf and flip through it absentmindedly until you spot a word that grabs your attention. This is a good way to find what new words might hold some reservoir of meaning for you.

2.) Torching the Modern Day Library of Alexandria, James Somers

Great read from James Somers about the world we almost got, where any book ever written was available to anyone and the bureaucratic dealmaking between publishers and Google that prevented it.

3.) The Editors Protecting Wikipedia From AI Hoaxes, Emanuel Maiberg

Pairs well with the above, giving a good overview of the modern spin on Wikipedia trolling threatening the trustworthiness of Wikipedia. Previews fascinating (and terrifying) possible futures that overlap with ideas like the Dead Internet Theory and even Kessler Syndrome… where we create an information ecosystem of half-truths, truths, and complete fiction—until we find ourselves trapped in an orbit of self-replicating misinformation, unable to free ourselves from a system we no longer trust.

That’s all for now, thanks for reading! As always I’d love if you dropped me a recommendation (podcast, reading, song, whatever) in my public rec box or in the comments here. I am especially on the hunt for the best interviews or documentaries with writers. Here is a good one from Sam Anderson on Haruki Murakami and another on John McPhee.

If you enjoyed this post, please consider subscribing so you get one of these each month and help this blog grow.

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In case you missed them:

• Coolest Folks I Discovered in 2024

• New Year’s Clarity: Why Wait a Year?

• 2025 Rough Draft: Reviewing 2024, Prepping for 2025

2024 was fantastic and busy.

I started a new job at a fast growing startup (we just announced our series B, woo!), flew all over the US and to Brazil twice for it. It continues to be wonderful and exhausting in the way you want something like that to be wonderful and exhausting.

At the start of 2024 I also launched Cubicle, a simple Pomodoro based task management app. That ended up finding 25ish users and paying for its own domain to live on for another few years… which is cool!

My Substack also grew. I posted 17 posts + essays here and passed 100 monthly readers early into 2024 (approaching 200 now). My personal favorite thing I shared here was either my essay Fasten Seat Belt While Seated about my final work trip at my previous company or Do I Dare Disturb The Universe? a very personal exploration of the past 10 years of creative work. The most popular post of the year (and of all time for me) was I’ve built a city, now it needs residents about my project Greenwich. That one is my first piece of writing to be read by tens of thousands of people rather than hundreds.

Speaking of Greenwich… that was a super fun project from the year. It was purely an experiment that grew from a burst of manic weekend creativity. Allowing space for stuff like Greenwich is super important to me. It’s nice when these experiments come somewhat fully formed, with a strong aesthetic and functional concept. The project got a lot of love online which is always encouraging.

Printernet also continued humming along in 2024. By April, we’d surpassed the total revenue Printernet had accumulated ever in just those four short months. This was wild and inspiring for me. Later in the year, I got the chance to parter with Sublime and launch Woah through Metalabel, featuring interviews from brilliant people like Anjan Katta (Daylight Computer) and Melanie Masarin (Ghia). That sold out immediately and ended up doubling the total issues I’ve shipped since starting Printernet. It was delightful collaborating with Sari, Alex, and Gabe over at Sublime and reaching a few new countries we hadn’t shipped to along the way.

I also moved to a beautiful new home, witnessed a total solar eclipse, turned 28, visited Mexico + Mexico City for the first time, celebrated my first anniversary since Tessa and I got married, met my new Nephew for the first time, saw Dr. Dog at Red Rocks, visited my brother in law and sister in law’s gorgeous home in the Washington woods for the first time, got to go back to our family’s annual beach trip for the first time in 10 years, hosted the Austin HTML Day meetup, got a new pup named Alfred, and more. It was truly a wonderful year.

For 2025…

I am focusing on a single project at the moment that I am not quite ready to share more about. But it was the answer to one of my New Year’s questions: “What’s one thing I’ve always said I wanted to achieve but haven’t started (or finished) yet?” This sort of singular focus is a way of working I’ve been feeling pulled to for a while and one Tim Ferriss endorsed when I asked him how he juggles multiple interests so effectively at SXSW 2023. This project, if executed well, will run up to May / June. I feel patient and calm about it.

I have a similar idea for the second half of the year - focusing on a singular project that also satisfies that same New Year’s question above… but I am deliberately keeping the vision for that fuzzy for now.

For the especially curious, there are clues to both of these projects over at my personal site.

Other things I want to do this year:

• Continue to travel and visit family (this is an emerging source of joy for Tessa and me and I’d like it to continue). I am heading to São Paulo soon and will also likely have a mid-year international trip with Tessa if things go our way.

• Keep meeting and talking to interesting people making cool things. I’ve already had one fantastic conversation that was recorded and should be available soon. More of that and sharing “Season One” of my podcast is something I’d like 2025 to involve.

• At work I’ve transitioned to a leadership role on the management side of things and look forward to learning tons around this. It’s already proving to be fascinating and full of new challenges and games. By the way, if you have a go to resource for lessons / ideas around effective leadership (particularly in a Startup context) I’d love to check them out.

• Turning 29… it’s a cliche to be swept up in the surreal nature of time passing but I do feel this way at the idea of entering my final year of this decade.

• Continue writing here and over on my site. Writing publicly continues to be my longest running project and one I plan to work on for my entire life.

More updates soon, as always, thanks for reading! If you want to help directly support my writing you can subscribe here.

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Wishing you a wonderful year!

Jake

Of course this is somewhat arbitrary. Why wait until January to do this?

Can this same reset we associate with the new year be cultivated every quarter of the year? Can I reorient myself in such a way that allows me to access this higher level view of my goals and the reality of my actions every few months? And what would doing so do, for me? What are the characteristics or routines of the new year that allow for this clarity of mind? Perhaps I can recreate those same conditions more frequently.

The coffee is almost ready and I’ve got a year to get to… so I will wrap up this working note quickly.

Here are a few questions I am thinking about this January in this brief window of renewal that might be interesting for you to think about to:

• What do I wish I’d done last year?

• In December of 2025, what will I wish I had done with my year? If I could write my 2025 summary, pretending the year was over, what would I like to include?

• Five years ago what was I after? How has this changed or been accomplished? How do the next five years fit into what I’ve been doing, or wanted to do, since 2020?

• If I could only do one thing really well this year, what would it be?

• What’s one thing I’ve always said I wanted to achieve but haven’t started (or finished) yet? Hat tip to inkko on this one.

• Which unfinished projects deserve a conclusion and which can I safely let rest?

• If I had to oversimplify my plan for getting what I want this year, what would it look like?

• Has anyone with less motivation, skill, resources, or information done what I am looking to do? The answer is surely yes. What does that do to the excuses I might present myself with?

• Which projects and people really inspired me last year? What was it about them? What reflections of my own ambitions or taste did they provide? How can I help the same people or projects or similar people or projects this year?

• What do I want to keep doing exactly as I did in 2024? These are things to cherish and continue to water without taking for granted.

• What existing levers have I discovered or built that I can utilize this year?

I will leave you with the vibe I am cultivating for 2025. Wishing you a good one!

• Anu Atluru: wonderful writer (creativity, startups, etc), founder, great tweets

• Spencer Chang: brilliant inventor, very creative and generative, magic ceramic and more.

• Sari Azout: founder of Sublime, curator and generous resident of the cozy web.

• Alex Dobrenko: Sublime, collector of interesting people, honest and introspective writing.

• Jason Kottke: one of the coolest personal websites out there, consistently sharing the most interesting parts of the web.

• Matt Webb: brilliant inventor of things like magic clocks, on a 300+ day writing streak or something wild like that, his writing is very deeply researched but in a way that feels entirely casual.

• Kay van den Aker: inventor, interface design, AR, and more.

• Andrés Cuervo: inventor at Folk Computer, very deep knowledge of computer history and where things could go.

• Matt Muir: Runs web curious, a true internet collector and curator.

• é. urcades: trying to do very cool things at the Flower Computer Company to make everyday objects remember things and change based on their environment.

• Kev: internet collector and curator, fascinating experiments with “magic labels” sewn into clothing.

• Sam Peitz: designer building very human feeling, creative, tools.

• Jack Connor: OSV fellow archiving endandgered languages using traditional methods + AI.

• Cristóbal Sciutto Rodríguez: writer, collector, inventor (Folk Computer).

• Marisa / Design Team of One: designer and curator of cool things

• Juxtopposed: Awesome UI/UX designer making YouTube videos on UI/UX concepts, redesigns interfaces of famous software and documents them in a super fun way

• Ryan Mather + Kelin Carolyn Zhang: inventors, made Poetry Camera… the magic polaroid which composes poems based on what you photograph.

• Anjan Katta: inventor and founder, Daylight Computer Co, cool way of not going with the typical Silicon Valley thinking.

• Laurel Schwulst + Elliot Cost: separately, extremely generative creative people. Together, HTML energy. Elliot also co-created the Internet Phone Book.

• Kristoffer Tjalve: co-creator of the Internet Phone Book, extremely creative designer and artist.

  I reserve the right to add anyone I remember later who I truly discovered in 2024!

This isn’t always a problem, sometimes letting the right things percolate over months or even years can be mysterious and magical, ultimately improving the work. Rushing an idea or project is certainly its own kind of problem.

But, being afraid to share ideas that are under-polished can create bad creative habits. It can lead to more second guessing and doubt, perfectionism and even end in a project sputtering out and being abandoned. I’ve abandoned many projects unintentionally, because of inertia.

I’ve played with a few different solutions for resisting the siren call of perfectionism.

One is publishing less refined, more impromptu posts, over on my personal site. I call them working notes. They are meant to capture early ideas, inklings of bigger concepts or projects, or even random bits floating around in my head. And I’ve mostly reserved my Substack for the eventual iterations on those ideas, and I work harder here to dress them up (hopefully not superficially).

Having a place for your unrefined early ideas and a different place for your polished work is helpful for resisting perfectionism and keeping up creative momentum. Many people use Twitter for this too.

Another solution for resisting perfectionism is my framing of “experiments and endeavors”. If you have a cool idea, don’t think of it as a long term project but a short term experiment. If it turns out horribly, that’s ok, it was just a test. Nothing serious, no big commitment or time wasted. I also believe that most things we give our full attention too cannot “turn out horribly”, there will always be something gained from the attempt. This is called Systems Thinking: how can I benefit even as I fail? I’ve tried to keep this as a kind of mantra over the last half-decade.

The essence of both of these approaches is lowering the stakes of your work.

This becomes hardest when you know in your gut you’ve got something very good. An idea or prototype that could really be great, one that you suspect could be an endeavor or long term project. An example of that would be my essay on boredom or the Printernet web app I’ve been building. I don’t have an answer for those cases but I do think making a habit of sharing your ideas early and often helps over time. I am still struggling through this part. Some projects feel easier to “lower the stakes” than others. Could that be an intuition about where to focus your time? Maybe.

This little post is an example of trying to do this more though. I’ve been working on a lot of fun things and have not had time to simply sit and write lately. It’s been a tiny voice of anxiety in the back of my head. I suspect the next six months will be similarly busy.

So I will try to start sharing “working notes” here, little low stakes posts that sketch out small or new ideas, about the things I am working on or thinking about.

Have a great week!

If you don’t know, I run a company called Printernet. We let anyone create their own magazine subscription with reading perfectly suited for them. Think of it like Readwise, Matter, or Pocket… but the medium for reading the interesting articles and essays you save is a beautiful print issue without the distraction of the internet, delivered right to your door.

With Printernet, I also love doing special collaborations with the right folks… Sublime definitely meets the criteria. Sublime is building a more human “second brain”, a more intentional, creative, quieter side of the internet. You can read all the cool stuff they do here.

We teamed up to share 10 delightful and vulnerable conversations with wonderfully creative people. We are only doing 100 issues and I’ve just heard there are only 25 left… so get yours today!

Featuring Sublime's Alex Dobrenko in conversation with:

• Anjan Katta of Daylight Computer on building humane tech without losing your humanity
   

• Douglas Rushkoff on the case for not knowing—mysticism, machines, and why the future is human
   

• Yancey Strickler of Kickstarter and Metalabel on escaping the algorithm to build a creative career that actually sustains you
   

• Leandra Medine Cohen on starting over after Man Repeller’s public fall from grace
   

• Melanie Masarin of Drink Ghia on how to build a brand, the costs of authenticity, and the realities of founder life
   

• Mason Currey on all the ways artists, himself included, have balanced making art with making a living
   

• Isabel on what happens when you let go of cynicism and trust yourself enough to be positive
   

• Adam Mastroianni on what’s making us all so unhappy and what to do about it
   

• Plus a special conversation between Alex Dobrenko and

  Sari Azout (founder of Sublime)

Get your copy!

You can read more from Alex on what motivated these conversations here.

Have a great weekend,

Jake