🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

The reading influencers on TikTok seem to have accomplished something I’d previously imagined impossible: they’ve made reading itself a toxic competitive sport. It’s no longer enough to read a book, to love a book, even to like a book; quantity is now king for Booktokkers. And they’re not entirely alone in the pursuit of leaderboarding the written word; productivity hackers and bloggers have turned the accumulation of speed-read books into a metric for success too.

But I find “number go up” to be a terrible reason to read anything.

You may be able to mark a thousand books as “Finished” on Goodreads, but it’s not worth an awful lot if your mind remains empty.

John Locke, for all his failure to capture the short-form video market, said it perfectly in 1706:

“Reading furnishes the mind only with materials of knowledge; it is thinking makes what we read ours.”

As near as I can tell, there are three ways to read a book:

Accumulation Reading; the hoarding of pages, the finished stack as a trophy shelf. It’s the end result of reading in order to appear smart, accomplished, intelligent; it’s a form of reading as both consumption and performance. You don’t need to gain anything from the time you spend with a tome; nor do you actually have to enjoy it.

All you have to do is burn through a book and get to the finish line of being able to rack it up and post about it.

Neither passion for page nor progress is a prerequisite.

I’ve long accepted that listening to an audiobook counts as reading. I can’t accept that skim-reading a book in an hour, or feeding it to Gemini Notebook or Claude for succinct bullet points, amounts to the same thing. If you’ve merely existed in the same room as a book being processed - if you haven’t exercised your mind to process it yourself - you have done nothing, and you have read nothing. It might help you gain more followers; it might give you bragging rights among the insufferable, but there is little to be proud of if pride is found in something of worth being accomplished.

The second is Thinking Reading. It’s where you process a book the old-fashioned way - by considering it, sitting with it, and letting it cook. By poking and prodding at it with your mind, and letting it poke back. Letting it challenge you and mould you, or battle your instinct to resist the act of molding in the first place. Thinking reading is the only way you grow; it’s the only way you let information become a part of your personal corpus.

It didn’t used to be rare.

The goal of Thinking Reading is accumulation, I’ll grant that; but it’s the accumulation of actual knowledge. It’s growing the boundaries of what you know. The number of books consumed has no actual bearing on that metric. You can burn through the entire back catalog of Richard Feynman by whichever speedreading technique or chatbot summarisation you so choose, but you’ll learn a good deal less (if you learn anything at all) than you would by taking a month to read one of his books at the pace of a normal human being.

The third kind is Reading for Pleasure - a wonderful and noble pursuit. But a pursuit nonetheless; something that must be pursued. There’s nothing wrong reading a romantasy novel, or a Dungeons and Dragons supplement, or Dungeon Crawler Carl for that matter (I started it this week.) The requirements are simple: you must read with your mind in the present and on the page, and you must actually have a good bloody time while doing so. Once again - it has no relationship to your book-bodycount.

If all you gain from a book is a number to stack against your followers, and the people you follow, you’ll read in a shallow and pointless fashion, and you’ll come to the end of every book with only the most hollow and empty sensation. When you turn the last page, you’ll be functionally the same person who turned the first; and you won’t even have a few hours of joy, fear, adrenaline, or lust to make it worth your while.

A chapter chewed is better than a whole book gulped and swallowed whole. One book, well understood and carried for a year, dog-eared and worn down with fingerprints covering its pages and its slip cover torn and tattered, is better than a hundred books counted and listed and posted for public admiration.

Stop counting.

Start thinking.

Read like it matters.

(Because it does)

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Our entire attitude toward education is flawed.

We spend years in primary school and then secondary school being coerced into absorbing information and hammered with the misconception that the point of learning is meeting arbitrary goals and being measured on our ability to memorize facts and formulas.

That’s bad enough.

What’s worse, though, is that when we finally reach the end of that tunnel, we go through a graduation ceremony and treat it like a happy funeral for our learning period.

People give speeches, and everyone reminisces about a part of their lives that is over forever.

It’s a celebration of the fact that your learning is finished.

May you never endure the hardship of cracking open a book ever again.

We then believe that after only 18 years of our lives, we have gained the information and experience we need to deal with the next 60–70 years. That’s crazy. It’s a crazy attitude, but it’s one that almost everyone slowly adopts.

When School’s Out, Learning Lets Out Too.

Most people reach the end of their school journey, go through graduation, and then stop learning. They stop seeking out new information and new lessons because they’ve already been there, done that. They literally have a certificate.

And so the entire period in which they were at school being required to learn something that would improve their lives or equip them for the real world, that becomes their only education.

Sure, they can go to university or college and extend their formal education, but they’re back in the same sprint that they ran in high school. They’re trying to get through a track as fast as they can, and jump every hurdle.

But they’ll eventually reach another graduation ceremony and gain another certificate that says they’ve ticked the boxes and learned enough.

It is complete.

The focused learning just stops. They might be forced to learn some new skills at work, or go through a mandatory course. But they won’t try to learn something just because they want to improve themselves independently.

It’s the fault of the schools, sure. But it’s also the fault of parents who turn their children’s education into a painful, constant struggle. It’s the fault of education theorists and government regulators who are tasked with deciding what information, from the entire store of human knowledge, should be crammed into a little over a decade of schooling.

It all adds up to create a negative, dragging, shitty attitude to learning anything.

You Don’t Have To Let Yourself Graduate.

Here’s what I believe. I believe that structured learning doesn’t answer the entirety of your educational need. I believe that it doesn’t answer even 50% of it. I believe that it lays the groundwork for the rest of your life as a learner.

When you view your schooling and your college education as being the foundation, not the entire block, you can start to build on it. If you spend every single year until you die ensuring that you have continued to learn, that’s going to change your level of understanding, readiness, and general insight.

I think the greatest thing a person can do after their formal period of education is complete is dedicate at least some portion of their time, every day and every week, to learning. Really learning. Reading, viewing, and analyzing the information necessary to learn a skill, a fact, a new area of expertise.

If you never let yourself graduate, you will never let yourself stagnate. You won’t fall back on old, outdated beliefs, or forget the important principles and lessons you learned before. You will keep your mind active and your edge sharp.

You have so many opportunities to learn. Right now. From videos on YouTube to entire volumes of incredible, important books that are available as a free download on Gutenberg. Not to mention the online courses that will let you learn about almost any subject. Or failing that  -  Wikipedia.

The point is, your learning really doesn’t stop because you left school. It stops because you think you’ve done enough. And if you don’t take responsibility for continuing your education throughout the rest of your life, you’re the one who will pay for it.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

You will never be more fulfilled in your life than when you understand your own natural inclinations, figure out how to nurture them, and build // work in a way that honors them. You can spend an entire 80-year window of existence bucking against the person you are, alternatively hating and loving yourself, battling and embracing, trying to squash yourself into so many molds, trying to brute-force change, or trying to lay anchor and resist it.

And when you get to the end, you’ll feel nothing but exhaustion.

The only way through it all is to accept who you actually are.

You can change the quality of your work without trying to change your essential nature.

You can take ownership of that nature without throwing up your hands and disclaiming responsibility because it’s just the way you were born.

You can evolve, and you can grow - but you can’t do any of these things unless you know who you are in the first place.

I started rewatching the Kung-Fu Panda movies with kiddo recently, and I’ve been thinking about this scene ever since.

(Note: if you’re of the opinion that you can’t learn much from a kids’ movie, this is where you should probably stop reading. And unfollow/unsubscribe; it’s not getting better from here, folks.)

Oogway: “My friend, the panda will never fulfill his destiny, nor you yours, until you let go of the illusion of control.”

Shifu: “Illusion?”

Oogway: “Yes. Look at this tree, Shifu. I cannot make it blossom when it suits me, nor make it bear fruit before its time.”

Shifu: “But there are things we can control. I can control when the fruit will fall. And I can control where to plant the seed. That is no illusion, Master.”

Oogway: “Ah, yes. But no matter what you do, that seed will grow to be a peach tree. You may wish for an apple or an orange, but you will get a peach.” **Shifu: “But a peach cannot defeat Tai Lung!”

Oogway: “Maybe it can, if you are willing to guide it, to nurture it, to believe in it.”

My goal as a creator is not to become a different creator. My goal as a writer is not to become Hank Green or Malcolm Gladwell or Michael Lewis. It’s not to become Ursula LeGuin or Douglas Coupland. No, my goal is to be what I am; but find a way to be the best version of that.

My goal is to be a peach tree.

To be okay with being a peach tree.

To be a bloody good peach tree, that produces bloody good peaches.

I can go right ahead and demand apples, oranges, pears or roses from myself, and I can do that to my last dying breath. But it’ll be peaches all the same. Talent and discipline, ambition and the latest tools, even all the capital in the entire world won’t let me bear any other kind of fruit.

But how much of our creative frustration, our anxiety, our sense of failure, our obsession with comparison, is only the fault of our drive to become something we were never meant to be in the first place?

The Fantasy of Being a Different Creator

Re-invention is a wonderful thing. I’ve been working on a whole piece about it. But re-invention is not the same thing as attempting to change your entire nature, against your own nature.

David Bowie is possibly the most famous re-inventor - becoming a new artist, a new persona, with a new aesthetic every handful of years. But he never lost what made him unmistakably Bowie: his spirit, his energy, his passion for music, rhythm, and storytelling.

It all stayed the same. Goblin King or Thin White Duke.

But I think we can all agree - David Bowie would have never attempted to reinvent himself as a TikTok wellness influencer; it would have gone entirely against who he was. Not that there’s anything inherently wrong with TikTok influencers (not in the scheme of 10,000 years of human history and the eventual heat-death of the universe) - but it could never have worked with who Bowie actually was, in his core, under the makeup and glam boots and white suits.

When something isn’t working - when we’re stuck, when we’re plateaued, when we can see other folks in our various niches doing better than we are - the instinct for a lot of folks is to try to emulate them. To find out what’s working and copy it, and copy them, and as close as we can, to become them. It’s why you see novelists attempting to become short-form video influencers and non-fiction writers jettisoning their deepest takes in pursuit of virality.

But it never feels quite right.

Something is always just a little bit...off.

Admiration itself is a useful signal, and imitation a useful tool; but only in so much as they reveal something or amplify something of our own. Only in so much as they uncover what actually moves us, or expand our sense of possibility and experimentation. IE, fucking around as a creator is perfectly acceptable, as long as it serves some form of finding out. But if you take it too far - if you abandon your own nature - you’ll only confuse your peers’ excellence with the evidence of your own internal inadequacy, measuring your beginnings against someone else’s best work, and getting unfamiliarity tangled up in superiority.

You can grow like that beautiful tree over there.

You can stretch your limbs to the sky, etc.

But you can’t become it.

No more than it can become you.

Remember: the tree doesn’t apologize for its fruit. It grows toward the sun, it accepts the seasons as inevitable, and it bears only what it can bear.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

When I was in my early 20’s, I gave everything I had.

I approached every task, every piece from a place of cosmically important ambition. It all felt significant; it mattered so much. There was an urgent need to do more, to make more, to produce more, and to always be working on growth.

I think we all buy into that growth obsession, sooner or later.

It’s considered to be a universal good; it’s considered to be the only path that has value. We have to look for new ways to make more money, have more customers, get more done, and be more productive. We need lifehacks, shortcuts, quick wins, and top 10 lists.

Everything we do has to bend our wills and our hearts to growth, no matter what it means.

To me, it’s more important to follow the craft.

When I take on a project, my goal isn’t always to find passion in it. My goal isn’t always to love it. My goal is to be proud of each word I write, each shot I take, each app I direct, each website I build, each script I pen. I may not feel a spark of heat or joy, but I will do work that makes me proud.

And in that work I will follow my craft.

There’s work that makes you feel passion, and there’s bill-paying work, and I may not always get to choose the one over the other. I can seek passion, and I do, but when it’s not there, all I have is my self-respect and a certain level of care for the craft that inspired me to do what I do.

When I decided to take a break from working in tech startups, I didn’t take a break from doing the work I loved. I just did it less, and on the terms I wanted. I worked with a small VC fund on their comms. I helped out and launched a few products. And I felt satisfied, rejuvenated, and excited about it. I wasn’t working 12-hour days, hustling and grinding for growth.

Too often, I’ve felt that some of the founding teams I’ve worked with don’t care about the craft itself, whether it’s the words that build their platform or the creative work that tells their story.

They just care about whether work = growth.

I love writing, and I love designing, and I love making stuff, and yeah, I derive a lot of value and meaning in my life from doing that and doing it well.

But when growth is all that matters, that work doesn’t have innate value just because it’s great work. It only has value if it makes the graph point up and to the right.

After my hiatus, I decided I didn’t want to go back to that growth culture. I wanted to stay small. When I started my own creative firm, I never called it a startup and I never set the goal of growth at all costs. I figured on one thing: that if I could do good work that I loved, that I was proud to stand by — and do it without sacrificing myself along the way — I’d call it a life lived well.

Remember. You don’t ‘make it’ — it makes you.

In the growth paradigm, there’s a point in your life where your work has paid off, and you can be happy. When everything changes for the better.

I think when I bought into that, I missed the entire point. The work I did was all aiming at reaching one level where it’d be worth it. Instead of focusing on doing it for myself, doing it for the love of it, doing it for the people who enjoyed my music, all I gave a shit about was doing it so that one day I would be a big deal.

But you don’t make it in life.

You don’t make it in business, or in music, or as an artist.

You never make it.

It makes you.

The struggle, the trying, the striving and fighting and building, it makes you into something far beyond what you thought you were going to be. And you don’t always like it, but you can’t ever stop it.

You don’t make it, because you think making it means having your life change utterly, and having your past self shattered along the way. When growth is all that matters, that’s what we search for.

When growth is all that matters in a startup, in a business, in an agency — you’re only searching for the chance to be; you’re not focusing on the chance to do.

There is a difference between being and doing.

The difference between caring about what you do, and caring about what you’ll be.

The hardest part of accomplishing anything is always getting through what must be gotten through.

Doing the work that sits on your list for weeks on end, and ticking off the jobs that you hated doing, but still finding a way to do them with care and with focus. The work of an artisan. The work of a chef, who must prepare and cut each ingredient before the art that is truly great cooking can come together. The work of an apprentice, whose work matters in its tedium, because it enables the beauty of the finished design.

That’s what builds the world — taking pride in the day-to-day crap that must be done. The day-to-day stuff that you can’t avoid, and can’t pretend isn’t bearing down on you with all the weight it can muster, but still deserves a labor of love.

We kid ourselves into believing that if we made it, our lives and our experiences would change. We’d go from having to do to just enjoying being. As if, when we make it to a certain level, it’s all fairy dust and flights of fantasy and bottles of champagne. As if, when we achieve growth, we’ll live a life of comfort and meaning by sheer virtue of that growth, separated from our work and our craft.

But 80% of this thing we call living is about doing the small things that deeply matter, and doing them with care. It’s about the work, and the sacrificed-for moments of play. It’s really about cooking dinner, and feeding the cat, and snatching a few seconds to kiss the person you love before they rush out the door trailing scarves and notebooks and debris. That stuff makes us. It makes us into people with connections and a search history. It makes us into craftspeople. It makes us into creatives, instead of drones.

You have to try to care, though. You have to try to care about some of this stuff, try to care about the things that you do when you don’t feel like a winner. Because even if you do reach that far-away goal that you’ve been dreaming about, your life is still going to contain the same amount of day-to-day honest crap as before — if not twice as much — and if you haven’t found joy in your craft, or you’ve just separated yourself from it, you won’t find joy in what you do. If you don’t grow for the sake of growth, and you don’t abandon the work you love, that’s an existential crisis you might never have to face.

If you keep pushing to the point where you’ll feel like you’ve made it, life is going to make you into whatever it wants just the same. There’s no way around that. But you might reach the endpoint and ask yourself what’s left and what’s next, if all you’ve strived for feels like all you’ve lived before.

You can still be a dreamer, but you can’t let those dreams depend on a point of success and happiness. You have to let them be dreams about doing things, not being. This is kind of paradoxical, and it’s nothing easy at all. In fact, just wrapping your head around it could take a lifetime. It might even take you half a lifetime to agree with me in the first place. It’s taken me 31 years to get here myself.

But I believe I’m right. I believe doing is what counts, not being. I believe that there’s no such thing as making it; there’s just a long road that you walk the same way no matter how big you get.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I have developed a personal cheat code for life that might sound ridiculous to you, and it might in fact be ridiculous; but in the face of my own doubt, my fears, the unpredictability of every single day of my life since 2020, and the shrouded future of AI, disruption, idiotic politicians, Netflix cancellations and badly thought-out software updates, it’s the only thing I’ve found that works:

Faith as a survival strategy.

Hope as discipline.

Future orientation as leverage.

IE: for good things to happen, I have to blindly assume that good things are still ahead of me, no matter what my past experiences might suggest.

It’s incredibly easy to feel behind, disqualified, late.

To feel like you’re permanently marked by your past decisions, like there are more paths that are closed to you than open.

But in my experience, you can make an equally powerful case for continuing to believe in irrational optimism as you can for the doldrums of precluded fate; you can make a fairly compelling case for treating the future as unfinished, regardless of the evidence one way or the other, as long as you actively choose to make that case.

Read more

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Nothing we avoid ever actually goes away. You can duck and hide, you can run from it, you can lock it away in a box, but it’ll still grow roots.

It’s a small task today (no matter how daunting), but it’s a soul-crushing source of anxiety tomorrow. It’s one shitty but fleeting moment today, but it’s a debilitating Achilles heel in a year, worse in two, worse in three…

We hide from ourselves, too. It’s not just the things we do that define us; it’s the things we don’t get around to.

They constitute the people we never quite become.

Or just the people from whom we fail to evolve.

It was Joan Didion who said,

“I think we are well advised to keep on nodding terms with the people we used to be, whether we find them attractive company or not. Otherwise, they turn up unannounced and surprise us, come hammering on the mind’s door at 4 a.m. of a bad night and demand to know who deserted them, who betrayed them, who is going to make amends.”

I’ve written my share of productivity posts, but that’s not what this is. Productivity advice will tell you to use the right timer, color-code your calendar, eat the frog, and remain unattached to the geolocation of your cheese.

I want to talk about something that makes me far more uncomfortable: why I avoid the things I avoid. And why avoidance feels so rational in the moment, even as it rewires my psychology, and even as it costs me far more than I can afford.

Read more

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

We have the goals of going indie all wrong.

We keep glorifying the massive exit, the overnight success, and the hyper-growth as the only acceptable outcomes. If you don’t hit those milestones, if you don’t “make it” by the defined standard of Pop Entrepreneurship (the word according to yCombinator and Tech Twitter), you don’t count as a founder.

If you don’t have a book in Barnes & Noble and a Netflix-licensed show, you don’t count as a writer.

In fact, you barely count as a failure unless you manage to squeeze out a viral LinkedIn post about your “learnings...”

It’s a paradigm that almost guarantees failure for 99% of the writers, makers, hackers, and builders out there who aren’t (and will never be) lottery winners. The normal folks who manage to make a living doing their own thing, but don’t reach the level of success the media and trad startup wisdom finds satisfactory.

But we don’t all need to be unicorns.

Unicorns are glorious creatures, and when they die, they die glorious deaths. But they still die all the same.

I keep thinking about this tweet, from @dvassallo:

…it’s simple.

But it’s one of the most inspiring things I’ve ever read.

What if the goal is never to become a unicorn?

What if the goal is as small and attainable, as aspirational and brutal as this: become a cockroach.

Cockroaches survive. They survive disasters both natural and unnatural. They’d survive a nuclear winter.

And they represent the only meaningful level of success for the indie revenue Enjoyor.

Survive until tomorrow, and when you get to tomorrow, survive that, too.

The Cockroach Philosophy

I have spent the last week trying to embrace the cockroach as the ultimate entrepreneurial spirit animal. A cockroach has no ego, only the instinct to persist. A good many folks might find them distasteful and look away; I’m directionally okay with that. Being rejected isn’t something I’m scared of, and it’s hardly a deterrent.

The core traits I want to build are resilience first; then adaptability and then indestructability. These might be inglorious, but if they mean the difference between living on my own steam and my own skills vs. going back to a job on someone else’s paycheck, they’re more than enough for me.

I’m willing to scavenge for crumbs, if need be. I’ll chase tiny revenues and unglamorous niches, and I’ll sell whatever product and service I can deliver and get paid for, if it means preserving my runway and staying solo. Status has never appealed to me; if it did, I’d have stayed in law school instead of dropping out to hit the road and go on tour.

If I never make it out of the shadows and into the limelight enjoyed by the folks with an audience of millions, I don’t mind taking that L. As long as the L is accompanied by profit, that seems like a decent trade.

My focus is on longevity, not legacy.

Legacy means nothing when you’re dead.

The longevity of your business means everything while you’re still kicking around above the earth.

How to Not Die

I’m a writer, can’t you tell?

My financial survival comes down to this:

Does my monthly revenue exceed my monthly expenses by enough of a margin to breathe freely?

My mental survival:

How far removed am I from the crippling burnout and depression that dogs my footsteps (and don’t pretend that doesn’t apply to you too; you can’t bullshit a bullshitter, mate)

My creative survival:

Can I keep the projects I’m passionate about alive, whether I pivot or mutate, and find a new way to monetize without giving up?

Do Whatever it Takes

My goal now is to cut my personal and business burn rate to as close to zero as I can; to spend less every single month, until I am running on a shoestring budget - without sacrificing functionality, and without removing my own ability to scale.

Part of that has meant moving to open-source software, or rebuilding my stack on my own; part of it is just cutting out expensive foundation models and tools and using open-source and open-weight AI instead.

I don’t actually need to run Claude Max in order to grow a business as a writer and build indie apps; I can do the same job with Ollama, OpenRouter, and KiloCode at a fraction of the cost. I can switch to using Harper instead of Grammarly, and I can reduce my Google spend by moving to Proton, again at a much lower cost. Notion is harder to replace with a lower-cost tool. But Obsidian is right there…

I don’t have a coworking budget; I work from a friend’s cafe in exchange for helping them out with their tech setup, marketing, and analytics. When they’re closed, I work from my kitchen table or the public library.

Zero glamour, I’ll own that.

Glamour is overrated.

I’ve said yes to unglamorous projects and clients, too. I know the standard advice is to productize everything, say no to clients who don’t fit into a certain bucket, and be brutal with where you spend your time; and to a degree, I’d say I embrace that thinking. At the same time, I don’t reject opportunities out of a sense of ego either. If there’s money to be made, and it’s money that will support my addiction to the written word, I’ll take it.

It’s cockroach mode.

That’s the breaks.

I have swallowed every drop of my own pride. I’ll ask for help, and I’ll ask for support, and I’m ok with looking intensely vulnerable. I’ll borrow code and borrow time and barter where it makes sense. And I’ll tell the folks in my network if revenue’s tight this month and I need them to broadcast a callout for clients. I believe in the apps I’m building and the books I’m writing, and whatever it takes to keep them alive, that’s what it takes.

I know I’d get more clout bragging about MRR and ARR. I don’t play that game.

I tend to ignore vanity metrics. Followers and likes, shares and claps, boosts and whatever else the current platform darlings are pushing don’t actually pay for either rent or tokens.

So who needs them?

The Indie Survival Guide

This shit is a marathon.

Don’t sprint towards a cliff.

Your job is not to wait for the perfect post or the perfect book, the perfect app or the perfect course; your job is to publish the rough draft, launch the MVP, and optimize for revenue.

Sounds cold, right?

I prefer to call it realistic.

I’m working on a backlist of products, tools, and short books. One release doesn’t make a career anymore; you need every shot you can get, and the more runs you can take at it, the greater your surface area for luck. Artists can starve in misery pursuing their masterpiece, and good luck to them. I know what it’s like to not have cash to eat; I’m not going back there, no matter how much of a lousy sellout that might make me.

I’m not interested in a million followers or subscribers. That’d be nice, but it’s not a meaningful goal, and it’s entirely beyond my control. I can’t wake up in the morning and take a single tangible step toward it. What I can do is identify the 10 folks who’ve supported my work every week and reach out to them one-to-one with a DM and an actual offer of friendship. It’s a lot more sustainable than hoping for flash-in-the-pan overnight fame.

Doing things that don’t scale is a hack a lot of folks will ignore. But a personal message might mean the world to someone. (If you’ve subscribed this week and I’ve missed you, my sincere apologies! I’m on a staycation while my partner and my kid are away, and I’m trying to touch grass a bit more)

I tend to charge from day one. I ask people to pay me for my labor, and I’m happy to use that as a way to filter out the assholes who don’t value my work. I’ve learned the hard way that the people who get everything for free are the most demanding and the least supportive; they’ll shout and kick and scream all the way down, and never throw a dollar your way. I find them early, and I help them find their way out.

I don’t pocketwatch my competitors.

Actually, I’m not convinced I have any. There are other creators and writers and indie builders out there, and I don’t see the game we’re playing as zero-sum or fuck you so I can get mine. I don’t watch their subscriber count or envy their success.

When I read people like Paul Millerd, it’s purely because I love their work. That’s enough of a reason for me.

Finally - I make, write and build.

Every day and every night. I write at least 1,000 words every day on this blog, and 500 a day on The Daily General. I’m writing 700 words a day each on the two books I want to indie publish next. These are non-negotiables.

Re: Extinction Events

The extinction events are easy to anticipate:

Running out of cash, running out of runway, and going broke is number one. As much as I’d like to claim I’m so enlightened as to be able to let it all slide off me like so much water, that couldn’t be far from the truth. Some nights, I can’t sleep thinking about it.

Some mornings, I wake up in cold sweat with a sick sense of dread in my stomach.

But the solution is simple, and I know it well enough to follow and optimize for it in my sleep: bootstrap ruthlessly, maintain as many side hustles and revenue sources as possible, and refuse to deviate from the path.

Losing motivation is the deadlier risk. I know there are people my age with more stability and more wealth, people I know who’ve taken jobs at frontier model companies and big tech while I keep grinding. Some days, it’s harder to face the work than others. But the more I look for - and find - daily wins, the more habits I can build for motivation instead of waiting for inspiration as a gift, the closer I stay to the joy of being indie.

Why Outlasting Beats Winning

Markets change.

Competitors die, and new competitors are born; platforms evolve, and tech is a moving target, and the economy is variously fucked. But if you can survive, you are perfectly positioned, in the right place and at the right time for the next wave.

Effort generates compound interest. This is something I talka bout a lot: small, consistent steps build towards an unassailable moat more than any lucky break or moment of virality.

The cockroaches write the histories. The unicorns who flame out get buried and eventually forgotten, or simply held up as cautionary tales.

But actual success can best be defined as this: survival over time.

Cockroach style.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I don’t want to spend the next 5 minutes of your time hand-wringing like a NYT pundit.

I’m disinterested in passing judgment on my peers and the world around me for daring to commit the sin of scrolling through a phone; as far as I can tell, the tech influencers’ performative obsession with dumbphones has yet to save anyone from their isolation or rescue our social lives from their collective downward spiral.

But at the same time - we can’t pretend it’s not happening. Can we?

We can’t pretend that we’re as social now as we used to be; that we’re as connected to our neighbors, to our families, to our friends, as our parents and their parents. We’re tribes of one, increasingly cut off from each other and losing touch with ourselves, too.

It’s the modern paradox. If you can look past it, I envy you.

I find I can’t look away.

We’re hyper-connected, in the most shallow version of the word. We can - technically - reach out to any other human being, anywhere in the world and start a conversation. But we’re profoundly isolated - collecting lists of friends and contacts, while sending blue bubbles into the void.

I can give you stats, but you’ve already seen them.

I know you’ve already felt it.

We are a society that has been restructured for solitude, while being made less independent than ever, while our human biology keeps demanding community.

Something has to break.

Or perhaps, it’s already broken.

The End of the Third Place

When I was a kid, we moved around a lot.

We were an Air Force family, and my Dad was restless; whenever we put down roots, he tore them up again, and it was a new house in a new suburb, in a new state. Well, as soon as we settled in, I always did the same thing: I built a treehouse or a bolthole (or a make-believe TARDIS) where I could escape from Dad’s anger and rage and the noise of my world, and be alone.

It was my third space, and there was nothing unique about my urge to create one. We’ve always craved somewhere to go, somewhere to be, somewhere to belong, outside of our own four walls.

When more and more of us are living in rented dogboxes and working from home, variouisly broke and low on time, we need a “Clubhouse” more than ever.

But the third spaces are shrinking.

Cafes are still an option, but they’re running low on business, and they can’t absorb customers who take up space for an hour+ without spending enough to make their COGs worthwhile. And with the cost of living rising, how many folks can afford to buy 2+ coffees, a Danish and a cheese toastie just so they have somewhere else to exist?

We have fewer communal spaces now - and the ones we do have are losing funding and resources. Every suburb I visit now is trending toward commercialized, transactional environments. And I don’t believe for-profit businesses are a bad thing; I’m a part-owner of a bar and my mates run restaurants and cafes.

But a community needs something else.

You can’t build belonging around a bill.

We’re Individuals. That Didn’t Used to Be a Bad Thing.

…and it’s still not a bad thing.

Not really.

But it depends on your definition of the individual and your definition of independence.

We’re anti-dependent lately; we have a hyper-focus on the self.

Our New Self-Care insists we must avoid going out and having a couple of drinks as though it were a deeply sinful and taboo activity, that our spare moments must be spent at the gym, “training” - for what, it’s never clear - and avoiding anything that might constitute a vice.

TikTok’s would-be Freuds and unqualified therapy-speaking, totem-waving mystics keep telling us that we have to set boundaries; but the boundaries are selfish, and their adherents withdraw from their friends and loved ones over perceived slights and ambiguous and enigmatic “harms” that are ill-defined and ill met.

“I cut off my family. I cut off my sister. I left the group chat.”

We celebrate these things as acts of courage.

And perhaps they were!

But if you listen to the complaints of social media’s loudest sufferers, it’s hard not to suspect that if you’re that surrounded by that many toxic offenders, the one thing they have in common is you…

When it comes down to a personal choice, we’re picking loneliness. We don’t start families, we don’t date, we don’t settle down. Even “Settling Down” has mutated in its meaning; instead of seeing ourselves as courageous builders who create a settlement in the wilderness and build a home as a generational act, we hear the word “Settle” and assume its only interpretation must be “Settling” for less.

Builders and makers go viral on Twitter, decrying their mates who have given up their dreams and abandoned their potential if they have a kid, as though our biological purpose is to create the world’s 300th AI coding harness rather than reproduce.

We’re trending towards being alone.

And being alone doesn’t have to equate to loneliness.

But somehow, it does anyway.

Remote Working Isn’t Always a Good Thing

There are a million reasons why working from home is a gift.

But the more we lock ourselves away in our offices and endure Zoom calls and reply to torrents of Slack messages and emails, the less we actually interact with other human beings.

Remember those?

Remember how it felt to go out for a midday cup of coffee with someone you actually liked to break the monotony of your day? Remember casual workplace interactions where you had to actually apply your social skills in micro-moments of shared belonging?

Pepperidge Farm remembers.

Unless, of course, their workforce has gone remote too?

We’ve blurred our lines of demarcation. Home life has now become work life, creating bubbles of isolation, even from the people we actually live with. If you don’t pack up your bag and head home, if your work laptop is within arm’s reach, how present are you actually with your kid?

He wants to watch Avatar with you.

That’s a perfectly reasonable request.

But if you only watch it from the corner of your eye while you monitor a pointless Slack thread, you’ve failed to meet that request. You’re a hermit in your own home, cut off on your own couch from the people you nominally love.

The Illusion of the Feed

Social media is bad, blah blah blah.

You could almost copy and paste any other luddite-manifesto right here, and it’d make no difference. Why? Because we know it all already. There is nobody out there, nobody reading this, nobody scrolling past it, who genuinely believes social media is a Good Thing™️.

We’re not even in denial about it - we openly talk about how much the infinite scroll, the comparison compulsion, the outrage farming and the brain-rotting short-form videos are fucking with our mental health.

You can pitch it at any dinner party as an easy topic, and settle back to let a table full of people agree with each other that this thing sucks.

Doesn’t stop us, though, does it?

Even when we promise each other we’ll take a break, we’re right back an hour later, checking how many likes we’ve received on our brave posts about taking a break. I’d call it pathological, but the word has been coopted by the Instagram Amateur Psychologist Class.

The TL:DR is this. We’ve substituted the lowest-effort and lowest-denominator digital engagement and connection for anything approaching a deep, reciprocal relationship; and we’ve done it at scale and on the cheap.

The Single-Serve Entertainment Economy

On-demand streaming has increasingly slaughtered the time we used to spend on communal, water-cooler TV watching; and hyper-personal algorithms keep fencing us off from each other into isolated cultural experiences made Just For You.

In some families, the living room isn’t even multiplayer anymore.

You’ll have three generations, sharing the same space, in their own headsets and tablets and AirPods and binge-lists.

But it’s unnatural, and we crave something else. It’s why Christopher Nolan’s The Odyssey has dominated the internet for weeks; we desperately want something shared to fight and fawn over, something we can all hold, whether we hate it or not, that will make us feel like we have at least one thing in common.

Unfortunately, we’re a species drawn to convenience.

And algorithms are the pinnacle of convenience.

The Cost of the Anti-Social Century

Derek Thompson calls this the Anti-Social Century.

And that rings true as a diagnosis.

Americans are spending less time with other people than in any other period for which we have trustworthy data, going back to 1965. Between that year and the end of the 20th century, in-person socializing slowly declined. From 2003 to 2023, it plunged by more than 20 percent, according to the American Time Use Survey, an annual study conducted by the Bureau of Labor Statistics. Among unmarried men and people younger than 25, the decline was more than 35 percent. Alone time predictably spiked during the pandemic. But the trend had started long before most people had ever heard of a novel coronavirus and continued after the pandemic was declared over. According to Enghin Atalay, an economist at the Federal Reserve Bank of Philadelphia, Americans spent even more time alone in 2023 than they did in 2021. (He categorized a person as “alone,” as I will throughout this article, if they are “the only person in the room, even if they are on the phone” or in front of a computer.)

Chronic loneliness, depression and anxiety shouldn’t be the crises of our time. Surely, by now, we should be solving flying cars with Jetsons-level tech, not crying in the shower. But here we are.

We’re more anxious than ever.

We’re more fragile, too.

We’re sedentary and screen-obsessed, filtering our entire lives through glass rectangles on a yearly upgrade cycle. We’re more divided, more prone to living inside echo chambers, less likely to know the names of the folks who live one door over.

And we don’t trust each other.

In fact, we trust strangers on the internet more than the people we meet. Not that we “meet” them anymore; we don’t even make eye contact with strangers.

The Economics of Solitude

Living alone is a highly catered-to, optimized, and streamlined consumer category.

It’s no longer an economic impossibility, although it’s arguably more expensive than living in a unit. It might actually be the most monetizable human condition in history; it’s a condition of persistent pain and anxiety, and people in crisis are more likely to spend than people who aren’t.

We have single-serve meals and solo travel packages and now micro-living options built specifically for the family unit of one. And it’s easy to lay the blame for it on capital itself; but I don’t think there’s any grand plan here, enacted by some shadowy cabal to make us lonely and // or dependent. It’s simply capital pivoting to monetize the atomized individual, in the way that capital always adapts. The coordination failure and the profiteering happened at the same time.

A solo chef box is a relatively harmless product.

But we haven’t stopped there.

We’re in the early stages of AI companionship becoming normalized; virtual girlfriends (and much more rarely, boyfriends) and subscription-based parasocial relationships are getting normalized at an astonishing rate. The Pareto-optimal parts of our interactions and relationships (validation, comfort, belonging, the feeling of being known) are getting unbundled. And we’re making the high-variance friction of actual human relationships semi-optional.

The people who actually love you have their own needs; they get sick, they get sad, they get stressed out, and they might actually choose to abandon you. They have agency that isn’t necessarily used the same way as yours. But you don’t have to deal with that anymore! You can front a monthly fee and get a perfectly calibrated simulation of unconditional love and // or positive regard, whichever comes first.

And then of course - almost inevitably - you get the for-profit cleanup crew. You get the mental health and wellness industry offering remedial fixes for isolation. They have therapy apps and mindfulness retreats and affirmations and boundary after boundary, and now AI therapy too. Anything to slap a band-aid on the symptoms without addressing a single cause.

It’s an economy of rational agents, responding to rational consumer demand.

But it’s also a perfectly closed economic loop.

We created the ideal conditions for atomization, and then we sold ourselves a synthetic patch for the resulting void, and now we’re selling ourselves the emotional suppressants and painkillers to cope with the fact that the patch isn’t real.

The Urban Design of Isolation

If the first level of isolation is economic and the second digital, the third is spatial.

We’re building cities optimized for a Nash equilibrium of privacy. Every individual is either consciously or subconsciously minimizing their exposure to strangers and chance encounters; micro-apartments and co-living spaces are nominally designed to be millennial-friendly communes, but in practice they’re little more than hyper-efficient storage units for isolated individuals who sleep and work in safely demarcated boxes.

The aggregate result is a worsening social desert.

Meanwhile, those who can afford to are retreating from the shared world into gated communities with private amenities. The ideal is to pay a premium to ensure they never have to share a swimming pool with the public at large. Even the neutral spaces left behind are engineered against human lingering; our architecture is hostile, divided, and unergonomic; park benches ward off couples and families as much as the homeless; and unstructured public squares have functionally ceased to exist.

Our zoning laws - and of course, there are more and more of them every year - divide human existence into separate quarters and isolated pods for living, working, playing, and praying. You have to drive from one to another, sealed in a metal box, never actually interfacing with the ambient organism of a city full of living, breathing people.

Reclaiming Our Social Nature

If the gravity of everything we’re building and buying is pulling us toward isolation, how do we reclaim a social nature?

It takes a philosophical reframing of the entire concept of “social friction.” For the last fifty years, absolute convenience has been the supreme god of consumer culture, but it’s the enemy of human contact, friendship, and familial love. IE, if you actually optimize your life so you never have to go to the store, and you certainly never have to wait in line, you never have to talk to a cashier, ask a stranger for directions, or maintain the simple skill of small talk.

And yes, small talk is a wonderful thing. It’s the subtle glue that bonds us, far more than spouting off about whether or not we’re living in a simulation, or whether God or Elvis are dead. It’s talking about the weather, how much it sucks, and how much the crops need the rain, etc.

There are choices you can make - choices I can make. To go pick up Pad Thai in person instead of getting it delivered to your door via an app. To refuse to outsource every minor chore to a slab of glass and a service-economy. And yes, to wile away a few minutes of your time in low-information and occasionally cringe and embarrassing ritual of “chit chat.”

Believe me, it won’t kill you.

You need to have the tolerance to survive the initial awkwardness it takes to build a relationship worth a damn.

It’s Not Kids These Days

I don’t want to get to the end of a screed and be dismissed as though I have a problem with “kids these days,” etc. Of course, it’s not; it’s older generations retreating into Facebook, as much as Gen Z withdrawing into TikTok. It’s everyone. It’s probably you; and it’s definitely me, I’m willing to admit it.

If everything is loneliness, it’s a measurable and impending health crisis, with a mortality risk roughly the same as smoking fifteen cigarettes a day; and if we don’t stage an intervention for ourselves, we’re looking at a decade, and then another, and then a century of decaying cohesion, dying trust, and human thriving becoming near-obsolete.

Humans are biologically built for community.

Our operating systems might be hyper-individualistic now, but they’re still running on paleolithic hardware, and the problem isn’t with the hardware. Wanting to be around folks you actually give a shit about isn’t unnatural, and it’s not a weakness. It’s fundamentally what makes us human.

We’ve given up a lot. But we haven’t given away the whole game. Not yet. And until we’re all so many red-jump-suit-wearing Wall-E-ignoring space travelers, I think we still have a chance to reclaim the cringeworthy, meat-based relationships that actually built our civilization in the first place.

I certainly hope we do.

I’ll leave you with that; I’m walking down to the local bookstore and getting a black coffee. Wish me luck.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I don’t know who first told you that you couldn’t.

It might have been your parents, a teacher, a well-meaning family friend.

But somewhere in your origin story, somebody looked at you and decided you were too weak or too small, and told you the dreams in your head were outside your reach.

They told you that you weren’t meant to be a dancer, or an artist, a programmer, a games developer, a performer, a musician, an entrepreneur.

They said it because they looked at you and saw themselves: who they’d wanted to be, who they became instead, and every belief they’d collected along the way about what a life can and can’t hold.

Maybe they were trying to spare you the way their own heart broke, and maybe it was love that made them do it. Or maybe they just thought little girls should be ballerinas and little boys should be CEOs. Either way, they were trying to press you into their shape, pushing when you didn’t want to be that or do that, and they weren’t the only ones doing the pushing. Everybody who told you to play it safe told you the same thing. Never start a business, never join a startup, never be a comic book artist. And when you pushed back, they told you that you were going to fail.

They drag you down, call you pathetic, predict your ruin, mock you, laugh at you. You can burn all of it. There’s no more reliable fuel than the need to prove those assholes wrong; it will get you running when your body aches and working when your eyes are closing.

You’ll never reach a point where people stop telling you No, or stop describing the failure you’re supposedly hurtling toward. F\*\*k them. Nothing will ever oblige you to believe them. “Stop kidding yourself” and “I’m just trying to be realistic” are opinions with better PR.

When people hand you limitations, they’re handing you *their* limits, not laws, and you don’t have to build your walls around them. Some things really will limit you, as they do everyone, but those things don’t arrive as a gift from somebody else.

When people told me I could never build the life I wanted, it became fuel. When they told me I could never do it my own way and be happy, it became fuel. When they told me I didn’t stand a chance, it became fuel. And it got me here.

For all I know, you could change the world. Whoever is reading this could be the art student who goes on to draw a comic that changes my life, or design the shoes I wear and the car I drive, or write the book that reshapes how I see things, or record the punk rock anthem that makes me break down and cry.

You get to make that happen, because you’re the one who can say Yes to it.

When I think about the people who have already changed the world, I don’t think of demigods. I think of human beings who were told No, looked up at whoever said it, and went out and did it anyway.

I think about the ones who take the shot without knowing what happens next. There have been hundreds of thousands of them, and there will be hundreds of thousands more. People who hear the limits and reject them. People who ignore what everyone else wrote down and write something new. People who do it themselves, their way.

People like you.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Everyone wants something for free.

Everyone wants you to give them your labor and your value for free.

They’ll offer you exposure, or they’ll offer you a chance to build your portfolio, and none of it means jack. They’ll devalue the years - literally, years - you’ve spent growing and honing and building your skills, through sheer blood, sweat, and tears, by trying to barter it out of you for exactly zilch.

And when you say no?

When you tell them you can’t afford to work for free, because you still have to pay for your own rent, your own bills, and your own food out of somewhere  -  they act like you’re the entitled one.

They act like you’re the asshole.

Their message is this: “If you don’t help me for free, you’re a bad person.”

And their attitude is, if folks like you and me don’t drop everything we’re doing to make everyone else’s projects our personal business and top priority without charging a dime, we’re so many frauds.

It’s pretty toxic, but unfortunately,  it’s something I’m quite used to.

It’s the opposite of collaboration - it’s nothing more than extraction.

There are some folks who will always try to get something for free, if they can.

They try to get something without offering even a fraction of its value in return.

And if you work for yourself, if you’re a writer or a creative of any kind, if you’re a small startup trying to gain ground, you’re going to be confronted with this kind of fuckery over and over again.

One publishing company approached me recently and offered me a book deal if I agreed to $0 upfront and $0 on every book until they’d reached x amount of sales, at which point I’d get 10%.

It’s ignominious to the point of being insulting.

And it happens in all the work I do. I’ve had startup founders harass me via my emails because I wouldn’t work for free at my agency and had the audacity to insist that my award-winning work has real-world value. I get the same messages at my bar from influencers who want a free night out in exchange for “exposure.”

You almost feel guilty when you ask people for money, and they come up with a creative way of telling you to piss up a flagpole.

But that guilt has been carefully manipulated by these folks in order to keep you working for free, for as long as possible.

Read more

My argument is simple: if my happiness makes you hopping mad, the problem is you.

Taste is personal.

It’s shaped by your life, your memories, and your tribe.

It’s a weapon in nobody’s hands, and it’s a crown on nobody’s head.

Rage at the “popular thing” is usually a mask for something else - grief, envy, a lost sense of wonder - and the healthier move is to feed your own mind with the things you actually like, instead of policing everyone else’s fun.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I’m broadly aware that the numbers aren’t great.

Someone told me last week that 99% of newsletters fail in their first 90 days, and that feels directionally accurate.

They’re easier to produce than podcasts (which have a famously high quit rate) but most still won’t make it past their first month, let alone their 10th issue.

The ugliest read is this: there is no market, no niche, no audience, and no subculture, subcategory, or Substack community waiting for your hot take.

Nobody asked you to write a newsletter; and as a baseline, nobody gives a shit whether you do or you don’t.

But in my fairly qualified opinion, you should go ahead and write on anyway. Write it how you want, write it where you want, and publish it no matter how much it might feel like screaming into the void.

Because the best newsletters in the world were written by folks with a bone to pick and an itch to scratch, who had no actual evidence that the world wanted it.

And they did it anyway.

The Brutality of Math

I’m not a fan of the art // science // vocation of mathematics. My Dad was a math teacher.

We don’t talk.

You do the…well.

That being said, some of the numbers are tough to ignore. Substack has 35 million registered accounts, and the top 1% of their newsletters capture roughly 90% of the attention, revenue, and readership.

And Substack isn’t the only fish in the pond. There’s Ghost, Beehiive, Medium, MailChimp, Patreon, LinkedIn Newsletters (for some God-forsaken reason), and something new launching somewhere new every week. The competition grows, whether any of us like it or not. The creator economy isn’t a zero-sum game, but it often feels like a pig trough constituted of 50% shit and 50% swill, with all of us fighting for the few scraps of protein that found their way into the muck.

If you do get past your first 10 issues, your growth is going to be flat for months; sometimes, years.

“Build it and they will come” was always a delusional myth, but it’s worse and harder now than ever before.

That’s the bad news.

But the good news: if 500+ newsletters launch today, and 490+ of them are functionally dead inside of 6 months, you don’t actually have to compete with most of them.

Your actual competition is:

1. The 10 or so newsletters out of every 500 that don’t throw in the towel, and

2. Your own instinct to throw in the towel

Why you should start anyway

If your only reason to pursue writing is fame, financial freedom, and the loving embrace of an audience, your “writing journey” is very likely to end in utter and complete misery. That’s the breaks.

But we don’t write for that - do we?

Outside of the grifters generating blog posts for an audience of unwitting slop-consuming subscribers, most writers write for a different reason entirely.

We write to think; both in private, in the sanctity of whatever app we choose, alone with our thoughts, and in public when our words reach total strangers who can mirror them back to us and help us see things we’ve missed.

That’s quite a wonderful exchange.

It’s one of the main reasons I ever sit down at a keyboard or pick up a pen; the other being connection. I write so that I might not be alone in the world. I don’t think anyone can argue with the value of that.

A newsletter forces me - and will force you - to find the clarity we won’t get from a private note, or a locked diary. To sort the firehose of nonsense that comes from my brain into something a single other human being can make sense of takes an enormous amount of effort; and it only happens through brutal editing, harsh re-reading, and the act of being entirely honest with my own thoughts, about my own thoughts.

I am convinced my future self will thank me for the archive, and I suspect yours will too. Yes, memory is the diary we all carry with us - and thank you for the reminder, Oscar - but my memory is a fucking sieve. A public blog is the best patch for it.

And while the silence may be hard to face, even the smallest audience compounds. 100 true fans will always be superior to 10,000 casual scrollers who delete your email as soon as it lands in your inbox, or 20,000 assholes who immediately forget signing up and angrily email you to lay blame for their own inability to navigate the internet like an adult with agency and a functioning brain cell.

You’re not writing for today’s audience of one, two, three people + your cats and your favorite parent. You’re writing for the audience you’ll only build in 2 years if you stick with it, and you’re writing for yourself.

The Real Reason You’ll Quit

Writers don’t quit because they’re actually defeated in any measurable way. They don’t quit because they lose the ability to put words onto a page. They quit because they expected X amount of growth in 30 days, and they never built the resilience it takes to handle the rejection of their own self-set metrics.

They quit because they compared their third issue of a newsletter they’d barely started - with a voice they’d barely defined - to issue several hundred by a Substacker with 1m subscribers, for whom Substacking is a full-time job, supported by a staff of 10+ people and a snack budget.

They quit because they treated their newsletter like a one-and-done product launch that either sinks or swims; when in reality, it’s a brutal, grueling, painstaking practice that takes time to grow.

The easiest analogy is a kid who gives up on their vegetable garden because a prize-winning tomato failed to grow overnight.

(It was me; I was literally that kid.)

Surely, we’ve more guts, and we’re at least slightly more realistic than that.

What Does “Nobody Wants This Actually” Mean?

The market isn’t owed your work, and you’re not owed the market’s attention. That’s as good a place to start as any.

But where to, from there?

If you don’t start a prairie fire with your first missive, it doesn’t actually mean you’re wrong, your blog sucks, and you should go fuck yourself. Sometimes, it just means you’re early.

And even if it does suck - you have permission to suck. For as long as it takes to get better; for as long as it takes to find a voice you love.

It’s not all bad, even if the silence is deafening. Low attention means you have a higher risk threshold to try things. You can throw shit at a wall and see what sticks; you can experiment, and mess with the form, and do the unexpected. When you’re small enough to have a sandbox to play in, you have a degree of freedom some writers would envy.

The best voices sounded weird as all hell before they became so well known that we took them as Gospel. The weird is a good place to be. Enjoy it.

Tim Ferriss’ first blog posts had comments and readership in the single digits. Ben Thompson of Stratechery fame wrote for years before it became a career. James Clear blogged without a book deal for years before our habits became variously atomic.

They didn’t wait for permission or for proof. They wrote through the void.

They treated writing as a craft, and a joy, a challenge, and an outlet.

And so can you.

How to Write When Nobody is Watching

Pick a schedule and stick to it. Exceptions are fine as an exception, but consistency is your only edge.

Write about something you can’t stop writing about. Don’t waste your energy chasing analytics, trends, or wherever the influencers think the puck is going to go. The influencers are idiots. I should know; that’s what people call me.

If you can resist it, don’t even look at your numbers for the first six months. Pretend they don’t exist. Pretend they’ve never been invented. Write, ship and repeat without post-gaming. It’s liberating, and you’ll skip the pressure, the self-doubt and the anxiety.

Read widely. Read often. Read every day. Read people you love, and read people you hate. Read books, blogs, magazines and shitty AI-slop posts on LinkedIn that make you just mad enough to serve as fuel.

But read.

Finally - publish. You can’t grow if you don’t post. You can’t think in public if you hide in the dark. Your work might be impossibly mid, compared to whoever you’re following. But if you publish it, and you don’t rage-quit, you can take solace in knowing it’ll also be impossibly mid compared to your own work in six months.

Samuel Johnson Went There First.

Samuel Johnson, writing in the 1700s, published The Rambler to a tiny audience, in a crowded market of London Circulars, in an era where most folks couldn’t actually read in the first place. He wrote, no matter how daunting it might’ve seemed. And we remember his name, while a good many of his competitors and contemporaries lie in forgotten graves.

You have distribution channels he could never have imagined. You have tools beyond his wildest dreams. You have access to more inspiration, to more of the written word than anyone, anywhere, at any point in human history.

If the odds feel stacked against you, I’d encourage you to look for the balance. It’s there, if you want to see it.

Take one thing away from this:

I want you to write.

I want to have more competition. I want more folks filling up my inbox, as long as they’re writing from a place of genuine passion; as long as they actually give a shit.

I want you to write a newsletter.

Even if nobody else does.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

Something that seems to make some people extremely uncomfortable:

A lot of folks like comic book movies.

And I am one of those people.

We like to clap and dress up, and we cry when heroes fall. We like to have a good night out at the movies, and we like that night to involve various caped demigods, mutants, and wizards. We find it inspiring, uplifting, and ridiculously and unapologetically exciting.

In short, we love watching the Avengers.

But there is a certain incredibly angry kind of person on the internet who sees our joy and feels nothing but impotent rage. They crash out, and they call us dumb, and they kick and scream about how comic book movies are trash and culture is dead, and we’re all garbage people for consuming garbage content.

They post long Twitter threads and ranting YouTube videos looking down on the “basic bitches” who enjoy mainstream pop culture.

If you ask me, they don’t seem like happy people.

And, well - I don’t think the movies are actually the problem.

I don’t think any of the juggernaut superhero franchises are the problem.

I don’t think my happiness, or the happiness of anyone who enjoys watching Iron Man or Captain America or Shang-Chi or the other paragons of the pantheon, is the problem either.

No: If your reaction to popular things is to lose your proverbial shit and rend your proverbial garment, the problem is very clearly and very simply with you.

If my joy makes you hopping, steaming mad, you should look inside the cave instead of looking at everyone else and pointing the finger of doom out of your own emotional dysregulation and your own inability to articulate and deal with your Big Feelings.

My Hot Take Is That Joy Is Not a Crime.

People are allowed to like things.

People are allowed to have fun.

We’re allowed to be moved by movies about heroic figures wearing red capes.

We’re allowed to love big dumb space operas.

To treat joy as if it’s the sole product of a weak mind, and to treat fun like some form of moral failure is a moral failure in itself.

Robert Louis Stevenson said, "There is no duty we so much underrate as the duty of being happy. By being happy, we sow anonymous benefits upon the world, which remain unknown even to ourselves."

Fandom, the act of enjoying something and becoming part of a tribe of people who enjoy that thing, is not a disease. And your personal taste does not equate to an IQ test that determines whether or not somebody is enlightened or a member of the Sheep Class™️.

My joy doesn’t actually need your approval.

It doesn’t need anybody’s approval.

If I’m inspired by something, I have every right to be, and nobody has any mandate or God-given right to make me feel ashamed by it; and if I’m happy and no one got hurt and you’re still angry, that anger is your fault and your responsibility. It’s certainly not mine.

Taste is incredibly personal and weird. It’s shaped by your life, by your memory, and by your tribe. But it’s not a weapon, and it’s not a crown; it’s not proof of a good soul or an elevated IQ. And it’s certainly not a reason to spit on people because they like different things than you.

It’s only the snob who says, “I like better thing, therefore I’m smarter than you, and you’re a plastic person and your fun is fake.”

And the snob is very rarely happy.

Liking serious films doesn’t make you noble, and liking old books doesn’t make you deep. Hating Marvel will not make you either a prophet or the savior of modern culture.

In fact, publicly and loudly hating any popular thing won’t actually make you free; sometimes it just makes you incredibly isolated. You might take some solace in feeling awfully superior in your isolation, but it won’t make you any less lonely.

A far better stance is to like what you like and let others like what they like.

You don’t have to turn your taste into an exclusive club, and you don’t have to beat the happy people around you to death with that club.

If you’re angry at a movie, it’s worth asking, am I actually angry or am I tired, lonely, and bored?

More often than not, rage is simply a mask for grief and fear and envy. It’s easier to feel anger than it is to admit that you miss your own sense of wonder and you don’t know how to get it back, or you desperately want to fit in with the mainstream and you don’t know how, and it makes you feel angry and left out.

There’s a hidden wound here; why do they get to enjoy this thing? Why don’t I feel anything? Why is my world not made for me? Why is my taste not popular?

It’s a form of projection.

You’re projecting your emptiness onto our excitement, your bitterness onto our popcorn, and your contempt onto our night out. If the joy of others feels like an insult to you, the wound is yours entirely, and the wound is yours to heal.

Something Being Popular Is Not the Same Thing as It Being Bad.

Just because something has mass appeal doesn’t make it empty or soulless.

Just because something is small and limited and exclusive doesn’t make it pure.

Sometimes a popular thing is bad, sure, but sometimes a popular thing can just be popular.

It can be fun, and mean little, and that’s okay too.

It can bring people together, bridge gaps, and give folks something to have in common.

Comic book movies can be corporate, formulaic, loud, and stupid, sure. But they can also be fun and moving and, in a way, beautiful and meaningful to some folks.

Two things can be true. Studios can want money, and viewers can actually feel real joy. A brand machine can be huge, and human moments can still be human.

It’s an incredibly lazy criticism to dismiss something because it’s popular, it’s a franchise, it’s for children, or it’s not real cinema. A much better criticism is to ask, what worked and what didn’t work? What did the movie do and what it failed to do? Why do people care?

You can hate the machine all you want, but hating the person smiling in a seat because their taste doesn’t match yours is petty and small-minded.

It’s a caveman-level scarcity brain mindset to think that my joy can only exist by stealing from yours. If you truly believe that the success of a mainstream movie crowds out your movie, that the flourishing of a fandom lowers the culture, and that the broader tastes of the Marvel fandom ruin the world, you’re welcome to keep on keeping on; but none of it is actually based on reality.

A great many joys can exist at the same time. A great many stories can exist at the same time. There can be infinite rooms and infinite fires burning, and you’re allowed to pick and choose. You can watch an art film if you want. You can read a hard book, and you can ignore the superhero movies. You can make your own thing. You can touch grass. You can leave people alone if they’re experiencing joy.

You don’t need to mock the fans and police what they love and rage post and perform disgust.

You don’t need to audit and censor everyone else’s taste.

The far healthier move is to guard your own attention and feed your own mind. If you want to build your own culture, do so. If you want to find your own people, do so. But if you can only focus on and expend your energy on stuff you hate, you’re going to have an incredibly miserable life.

If you truly hate something, if it awakens nothing but loathing, the best thing to do is to walk away, not to stand there pointing at it.

You Can Let People Have Dumb, Sacred Things.

Humans need myths and heroes; we need stories and tribes and costumes. We need to be able to feel something big and momentous that brings us closer to each other and gives us a shared sense of something bigger than ourselves.

Comic book movies might not be your thing, but they are a modern campfire.

They are a ritual of friendship that is much needed in what can be, for many people, an incredibly dark and unpredictable and anxiety-ridden time.

Marvel movies might not be for you; they might never be, and that’s fine. We can each have our own passions and our own tastes, but you have to go and find yours. If your sacred thing is hating everyone else’s sacred thing, there’s only one way that ends.

For everyone else, these heroes come to life.

These stories help.

These scenes heal.

These villains give us a way to channel and name our fears, and the endings give us hope.

You don’t need to join in, but you certainly have no right to sneer at us.

Being cold and mean and joyless and always above and apart from everyone else is not actually a sign of intelligence at all. You’re far more likely to find critical thinkers among the curious and the precise, the generous, and those willing to experience childlike delight. Calling everyone else dumb and complaining that culture is in decline and that you alone see and hold the truth actually makes you an incredibly lazy, boring, and self-indulgent critic.

A good critic asks, “Why does this matter? What need does this meet? What hunger does this fill, and what does the crowd feel?”

The intelligent understand joy; they don’t mock it.

They can see craft and commerce and emotion in more places than an arthouse flick.

They can hold more than one thing at a time.

Anyone can dislike a movie, but only a fool hates happiness. Millions of people enjoying a comic book movie is neither a crisis nor a plague, and it’s certainly not proof that the world has come to an end.

You can dislike it if you want. You can dislike the whole franchise. You can hate the entire genre. You can loathe the cape movie. But hating people for finding joy in it and building your own identity on contempt confuses bitterness with taste.

Am I harming you by counting down the days to the next Avengers movie?

Am I forcing you to participate by tweeting about it?

Am I stealing from you because I want to see it on opening night, or am I just happy?

Remember: if someone else’s happiness makes you angry, the problem is you.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

If you spent any time on tech Twitter over the past few weeks, you’ll have seen the same growing panic.

People keep talking about how the indie hacker economy is collapsing.

Revenue is down for anyone building their own app, and the money is leaving the space.

And the reason why is simple: everyone points to AI. The more AI tools there are that can enable anyone to build anything, the less people need the tools built by indie hackers.

But I think the core problem here isn’t actually that the indie hackers are losing market share purely because of AI. I think it’s more because the indie hackers’ entire audience has always been other indie hackers.

Revenues are dropping because everyone in the indie hacker space is building for everyone else in the indie hacker space, who is already building for everyone else in the indie hacker space.

When builders keep selling to builders, they’re selling to the very people who are the most likely to build their own SaaS tools.

They’re selling SaaS to SaaS people, tools to tool makers. They’re selling products for people who would always rather build their own products in the first place.

That’s the core identifier of their whole scene.

Which means we now have an infinite supply of micro tools being marketed to a shrinking pool of genuine buyers, with more launch energy than there is market demand.

Read more

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

You could make something right now.

If you wanted to stop reading, grab a sheet of butcher’s paper and brainstorm ideas; you could probably come up with half a dozen ideas for apps, books, or products.

Ideas aren’t the hard part, after all  -  just ask Tom Haverford.

Or anyone with “Serial Founder” in their bio.

You could build a WordPress site and start harassing your friends to test the concept. You could start writing op-ed pieces on Substack and put “Founder” or “Author” in your Twitter bio within 48 hours. You could throw up a landing page, post the first chapter of a book, and start pushing it on Product Hunt.

Where things get tough is when you’re trying to make something that people genuinely give a shit about.

You don’t want your dream to die in the chamber, because nobody read it, watched it, used it, or listened to it.

Because the deafening silence surrounding your work can crush your soul.

You want people to care? Here’s how.

1.

Only Make What You Care About

If you want to make something that people actually care about, you have to care about it yourself. Because if you don’t, then try as you might, it’ll come out in the final product.

The reason for this?

Making something is hard. Making something you don’t care about is even harder.

The only way you’ll be able to consistently work when you don’t want to work, consistently try when you don’t want to try, is if you deeply and honestly care about your work.

This has never been more pronounced. AI seems to be making everything from software to the written word all but disposable; and the temptation that comes with it is to make as much work as possible, while caring as little as possible, and doing it at scale. I keep coming across creators who are obsessed with automating the work into a content farm; they want the glory of the written word, but they don’t want a single letter etched onto their souls.

Unfortunately - whether or not people can tell AI-written content from human-written content, I think most folks have an almost supernatural ability to sense whether a creator actually gives a damn. We know when someone doesn’t care. We know when someone’s phoning it in. We know when someone doesn’t give a shit.

The good news is this: being deeply invested in the things you make, say, and do is a moat that few will bother to build.

So, rule number one:

You want people to care?
You have to genuinely care yourself.

2.

Make Things For Real People

The best writing advice I have ever heard was to write specifically for someone I know.

It’s a genius idea.

Every time I go to create something, or build something, I think about who I know that would benefit from what I’m doing.

If you have something that you care enough about to make, you have to ask the next question  -  who are you making it for? What information do they need? What turn of phrase would stop them in their tracks? What is their single pain point that the product could solve, or their secret story that your novel would be able to touch and cultivate into a real emotional response?

Stop thinking about your audience as a vague concept, a collection of faceless people.

Believe that your audience is a real person with feelings, experiences and a story. It will change your perspective.

The mass appeal of social media makes this a good deal harder; the fact that every post has the (technical) potential to reach an audience of millions encourages us to believe that an audience of millions is within reach, that our target audience must be so broad as to give us the best possible fighting chance of capturing the multitudes.

This is a false idol.

Your audience is as small as the thing you care about, and as big as the things they care about. That’s it. The work of it all is finding out what those things are.

You want people to care?
You have to know what will make them care.

3.

Ask Yourself If You Fit The Project

You need to ask yourself whether you have the courage, the strength, the motivation, and the passion to make what you want to make.

Do you have what it takes to do this, specifically this?

And I mean really ask yourself.

When you first come up with an idea, you can get so caught up in it that you can’t see anything else. You can’t see the toil on your horizon.

It’s easy to mistake excitement for passion, motivation and ability.

When that feeling starts to die down, or you get used to it, you can realize that you don’t have the real raw power to be able to finish and follow through. The idea was grand enough to spark action, but the long tail of effort doesn’t and shouldn’t belong to you.

Fact: there is nothing wrong with recognizing that a project isn’t right for you.

Maybe there’s another project that is.

If it’s not this one, it’ll be another.

It’s not enough just to care about what you’re making  - it has to feel right.

You want people to care?
Only work on projects that feel right.

4.

Don’t Do Anything To Be Someone

Have you ever watched one of those reality TV singing competitions?

You’ve probably seen a hundred young people, eyes shining, clutching microphones and talking about their dreams.

They’ll explain that ever since they were kids, they wanted to be singers.

Note that: BE singers.

Be.

They hardly ever say they want to actually sing.

When it comes down to it, half the time it’s because actually singing isn’t the end goal. They want the trappings, lifestyle, and breaks of being a singer.

If the act of singing was really their end goal, they wouldn’t be on a reality TV show. They’d be out there every night singing anywhere they could, writing songs, starting bands, recording music.

The same is true for anything you could make.

Do you want to make X, or do you want to be the person who made X?

Because if you don’t care about the act of making something, and if you don’t want to get out there every day and try to make something, you might as well quit.

You want people to care?
Care about your work. Not your title.

5.

Work. Work Hard.

If you want to write a book that can break someone’s heart  -  work hard.

If you want to start a business that changes the world  -  work hard.

If you want to draw a comic book that expresses everything you are and dream about  -  work hard.

I think we’ve overindexed on being anti-hustle culture. And to be fair, hustle culture itself was mostly bullshit. But the way to push back against it isn’t to insist that hard work of any kind is something to be denigrated, mocked, and avoided at all costs.

The hands of a craftsman or an artisan are made rough by the friction of hours at their work. That’s not altogether a bad thing.

I am the first to say that the pursuit of burnout is a performative waste of a good life. But I have never achieved anything by embracing the admittedly attractive notion that hard work is simply too much to ask.

It’s not.

I wouldn’t call myself a particularly impressive or successful writer, founder, or anything else for that matter. But I make enough money from writing and working and building on the internet to support my family; and the only way that happens is by getting up every single day and putting in the hours, whether I want to or not.

You want people to care?
Work hard.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I’m not a true believer in much.

I am a fanatical believer in reading.

I do it early in my day, I do it late in my day, and I do it often.

I keep the Kobo app in my iPhone dock, a paperback in my messenger bag, and my eReader never out of arm’s reach. If I’m waiting in line for a coffee, jumping in an Uber, etc, I’ll be nose deep in a book.

Why?

It takes serious concentration, and I’m addicted to focus.

We keep searching for lifehacks, productivity tips, and bullshit, but the answer is right there. If you want to be better, grow more, understand your life, understand your purpose, learn something, or just find somewhere to stay a while when life gets overwhelming  -  pick up a damn book.

Why You Should Spend The Majority Of Your Time Reading

The Pareto Principle states that 20% of the effort yields 80% of the results.

It’s the 80/20 rule.

I believe that spending 20% of your time buried in a book, buried in something that will inspire you, excite you, and make you want to jump out of your seat is going to give you the fuel, the ideas, and the power to create 80% of your output.

It’s worked for me so far. Every decision I’ve made, every idea that’s shaped the course of my life, every drop of sweat that I have spent trying to be a better human being, can be traced back to the power of a good book.

In other words?

Damn right you should spend the majority of your time reading.

You should be reading books, newsletters, magazines, and blogs.

Literally anything of worth and value to you.

Anything and everything.

Reading books will improve your vocabulary by 80%.

Readers have a 20% reduction in the risk of dying before their time.

Readers are 2.5 times less likely to contract Alzheimers.

And readers have a better handle on the various weaknesses of dragons  -  something that may or may not be useful, depending on your career path.

Reading can shape your path

Even if you have a clear as crystal idea of what you want to do with your life, it’s almost impossible to know the correct path to follow.

There are so many things that can happen along the way that it can be tortuously difficult to figure out exactly where you should be going and how you should be getting there.

But you have access to the entire archive of human knowledge up until this point.

In the pages of every book in your library, every book on Kobo, every book on Gutenberg. You have access to every insight worth exploring, and the answer is going to be somewhere out there.

I would guarantee that there is not a single question or problem you could bring to me that can’t be solved with a book that someone has already written.

And it could have been written 1,000 years ago.

What you should spend the majority of your time reading

Books: This is the most obvious. Books are filled with words, ideas, and information that will improve your experience of life. Most of your time should be devoted to books, at whatever pace and in whatever category you’re comfortable with. They’re the purest form of the written word, created with love and care, crafted and honed to their best possible form.

Other publications: There are many other publications, newsletters, and news outlets that can be a good way to spend your reading time. But you’ve got to be careful about it. Reading the news obsessively can completely destroy any time you had devoted to reading, and throw it away in favor of doom scrolling, easily leading you down a Twitter rabbit hole instead of leading you down Lewis Carroll’s rabbit hole.

Sometimes you’re going to want to read something that isn’t going to make you smarter.

Sometimes, you’re going to want to read something that doesn’t challenge you.

Sometimes, you’re going to want to read pure trash.

The good news?

Even reading trash is better than watching it.

Even reading trash is still giving your reading muscles a quick workout. That’s never a waste of time. I’m not saying that you should spend the majority of your time reading Star Wars fan fiction. That would be ridiculous, and it might give you some odd ideas (yes, there’s a fanfic where the Almighty Sarlacc gets it on in quite a graphic scenario)

I’m saying that you should give yourself space to read what you want.

It’s the reading that matters.

It’s the journey, not the destination.

Fuck podcasts. I’ll take a book any day.

When people say that reading is not as exciting as watching a movie, or listening to a podcast, I want to f**king scream.

They’re wrong.

Books are full of excitement and adventure. Books are beautiful and detailed. Books are the home of suspense and mystery. Books contain the signals that we have to reach for amidst the noise.

There’s nothing boring about the act of reading.

It might not be scalable. There might be more efficient ways of consuming content. But it’s the only way to retain and explore information that can afford it the respect it deserves.

I’ve never seen the point of blasting through as much as possible, as fast as possible, with your podcast player set at 2x speed. It’s a breakneck approach to consumption that seems harmful to my mind. And it cheapens the content itself.

Just Read It.

Reading gets perceived (by various influencers and hustle-minded assholes) as a waste of time, a distraction from other tasks, or even a leisure activity that should be left for lazy weekends.

Even if it were just a way to pass an afternoon, it would still be the single best way to spend your life.

But it’s not only a hobby - the ability to read is a tool. In fact, if you were to spend the majority of your time reading, you’d be well on your way to achieving happiness, success, fulfillment, and so much more.

Reading is one of the most important skills you can learn, yet it is one of the most neglected.

Reading can help you understand other people, cultures, and perspectives. Reading can help you develop empathy for others.
Reading can help you learn how to write.
Reading can help you become a better thinker.
Reading can help you conquer your fears.
Reading can help you relax and reduce stress.
Reading can help you be more productive.
Reading can help you solve problems.
Reading can help you live a more fulfilling life.

Make some time to hit the library this weekend. Pick up a book from the store on the corner. Go through your shelves and build a stack of books you bought that you’ve been meaning to read. And carve out some time for it.

You won’t regret one single, solitary second.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

The US AI companies are screaming about distillation.

(Again.)

To OpenAI and Anthropic, the idea of an open-source or Chinese AI company building their own AI by querying Claude, ChatGPT, etc is abhorrent - it’s a form of theft, taking that which doth not belong to them.

But there’s a deep hypocrisy at work here, and I don’t think it takes a highly developed moral compass to find it.

The US frontier companies built their own models on the entire corpus of human knowledge; they trained on books, images, music, videos, software and so on - entirely without the consent of the creators.

It’s the original sin of artificial intelligence. I won’t go so far as to say they stole these works - although in the case of torrented and pirated books, I think that case makes itself - but they certainly didn’t get permission from any of the folks whose work now constitutes Claude et al.

We weren’t allowed to opt out.

And in most cases, we certainly weren’t given compensation for our work.

In the vast scheme of things, this doesn’t actually keep me up at night. I’ve been writing on the internet long enough to know that my own work has been chewed up and digested by every model out there. I’ve understood that since the first models were able to do a passable job at generating a JA Westenberg-style blog post from first principles.

I remain largely unbothered by it.

Most of what I produce - including this blog - I consider to be open source anyway.

Reproduce it however you like; send me a link for my archives.

My problem is the moral inconsistency.

Defining Distillation

Distillation is when a smaller AI model learns from a bigger model. It’s almost copying homework; it extracts the patterns created by the frontier labs without having to copy the weights. The method enables AI models like DeepSeek to be built - and therefore, provided - at a fraction of the cost of US models.

According to the luminaries running Anthropic and OpenAI, this constitutes theft, inasmuch as it’s the unauthorized use of intellectual property.

But if Anthropic has extracted value from someone else’s work without permission, and DeepSeek has extracted value from Anthropic’s work without permission, I fail to see which sinner has acted more egregiously.

Both have used the output without direct permission; both claim:” Transformative use” as a defense. The logic is identical. If, as a writer, Anthropic has trained on my work without my consent, I don’t see that I should be at all invested in protecting Anthropic’s rights if and when Moonshot (the makers of Kimi) train on Anthropic’s work.

It seems a fairly clear-cut case of what goes around comes around.

On Power Asymmetries.

Anthropic, of course, has teams of lawyers, lobbyists, and flaks. They have an army of folks whom they can call on to protect their IP. The individual artists, creators, etc whose work wound up in their training data have no such advantages.

They have every right to attempt to use that army to fight for their commercial moat, but they’re playing a very different game than the rest of us. They’re not the victims here, and pretending to be so when their own logic is turned on them seems a bit rich.

A bully who goes crying when someone else punches back is hardly likely to garner sympathy from anyone but the bully’s own overindulgent mother.

If training data is fair use, it must logically follow that distillation is fair use; and if distillation is theft, it must follow that training is also theft. You can’t have your cake and eat it too. You have to pick one.

And the truth is, they already picked theft, by their own definition of the word.

Nobody in AI has clean hands; everyone is tainted to some degree by the original sin of training data. The entire stack is built on borrowed ground, and arguing about distillation won’t change that fact. I don’t think you need to abandon AI entirely because of it, but you do have to take the indignation of the injured AI labs with more than a grain of salt.

Anthropic and OpenAI forfeited the moral argument at the inception of their commercial models. They may be able to make a compelling legal case to the US Government, but they have no ethical case they can make that won’t show them up to be sore losers who can’t handle their own medicine.

Distillation is a mirror.

Just because the US labs hate what they see in it doesn’t mean the rest of us should weep tears of sympathy.

I cover:

• The actual comments Naval made about his schedule and his wife booking his time.

• Why the internet views this as wealthy philosophy instead of real wisdom.

• The “if you need me you’ll find me” problem and how it establishes a strict hierarchy.

• How survivorship bias plays into billionaire lifestyle advice.

• Why modern audiences are totally allergic to guru content right now.

If you enjoyed this video, definitely subscribe and leave a comment below.

Do you think Naval’s approach is pure freedom or a status flex?

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I’ll be the first to say I was a fan of Tim Ferriss.

Actually, scratch that. I am a fan.

I have all of his books, from The 4-Hour Workweek to Tools of Titans.

So what follows isn’t intended as a hit piece.

But I have a growing sense that the core argument of The 4-Hour Workweek itself - the thesis that we should be creating loops of income-generating work that remove the human from the loop - is both obsolete and dangerous.

The original book was the product of a specific moment: the explosion of online products and services, in a pre-AI, pre-remote-work-mass-adoption era, when time and geographical arbitrage still mattered.

But it’s not 2003 anymore.

It’s 2026, and passivity - whether it’s to do with your income or literally any part of your life - is dead.

The original arbitrage (and why it worked)

What Tim Ferriss actually taught:

You should outsource as much as possible to cheaper labor, automate everything else, and live like a king in Buenos Aires, Thailand, Bali, etc, profiting off the USD value imbalance and letting your business run itself as much as possible.

The advice was to get out of your expensive backyard, uproot, move somewhere cheap, and build a largely autonomous business that printed money while you slept. It was the OG passive income Bible.

The PI businesses of the age were largely informational: selling cheap physical products en masse under your own brand or selling PDFs of your domain knowledge.

They made money because information asymmetry still existed. Simply put: you could know things that other people couldn’t, and you could monetize that knowledge because it was actually in demand.

It was the “Muse” business model: create a low-touch product, automate fulfillment, and reap the rewards. You can still find various grifters pushing this model in 2026.

It no longer works, but it did work for Ferris and the cohorts who came directly after him.

The AI collapse

AI automated the tasks better than any of us ever could; but more than that, it flattened out the arbitrage itself. Every single tactic of the Passive Income gurus is now available to anyone with the cheapest possible AI // LLM subscription. VA work? AI does it for next to nothing, and better than a VA used to. Niche info products? AI can generate 100 in a single run. Dropshipping? Automated. Content farms? Dead. SEO arbitrage? Buried.

The moat, if there was one, was asymmetric effort. But AI removes the asymmetry. If it can be done passively, it can be done by AI, for everyone, digital nomads not required.

The speed of change is critical here too. Passively sitting back to let your business run itself = sitting out one of the fastest-moving periods of tech change in our history - and you’re missing out on every single opportunity that comes with it. The passive income model relied on taking advantage of tech to apply your arbitrage, but the tech is changing fast enough now to make any form of passivity a liability.

If your goal is to sit on a beach and glance at a laptop a few hours a week, you’re functionally behind.

But was any of it true?

Of course, if you pull back the curtain, passive income was never actually passive./ It took massive upfront effort, constant maintenance, algorithmic chasing,n customer service, and reinvention. Tim Ferriss himself worked constantly, putting in vast amounts of effort above and beyond the vaunted four hours, appearing on podcasts, writing books, doing consulting and speaking tours, angel investing, etc. There was nothing passive about the godfather of passive income at all.

And there was nothing passive about the work adopted by his disciples either.

The passive part was just outsourcing the visible work, while you did the invisible work of managing the machinery.

But the machine now runs itself, which means it runs for your competitors too. The only thing left is a commodification race to the bottom.

What replaces passive income? (active leverage)

AI creates infinite supply, meaning the only scarce resource left is human judgment, curation, and trust. If you define active leverage as using AI to amplify your output, not eliminate your involvement, there are massive opportunities that dwarf anything the passive income blogger could have dreamed of.

The goal is no longer 4 hours; it’s 40 hours of high-leverage work that produces 400 hours of impact.

If you’re actually present and accounted for, the power of a frontier model is incredible, and it will pay out asymmetrical rewards; but if you’re chasing passivity and attempting to outsource your entire existence to an LLM, you’ll be arbitraged to fuck by everyone else who still shows up with their brain attached.

And you’ll deserve it.

If you’re still chasing passive income, you’re building an obsolete 2006 business in 2026, and that only ends one way. Working 4 hours a week is more of a red flag than something to celebrate; it means you’ve removed yourself from the loop, abdicating responsibility, and automating yourself into irrelevance.

The irrelevant are replaceable.

And the replaceable are expendable.

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place.

While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs.

You can buy my book Permissionless here.

I keep seeing the same people crashing out over the same thing.

I keep being told that we’re heading for an apocalypse, and that I have either three, or six, or 12 months to escape the permanent underclass, after which the social order will have been entirely rewritten, and the haves (post-AI millionaires) will eternally rule over the have-nots (the rest of us chumps)

I’d expect to hear this from the AI doomers; it’s their bread and butter to spread the message of bleak determinism that says everything is over for the human species.

But they’re not the core culprits.

The culprits are the AI maximalists - the tech optimists and indie makers who are thoroughly AI-pilled; they're the folks who are the loudest about the “permanent underclass.”

I think the reason why is simple: they’re overexposed to AI; they’re on the cutting edge, consuming the latest reports, whitepapers, blog posts, tools, etc, and everyone in their bubble is talking about AI constantly. They can’t catch their breath. They’re operating from a very human place of anxious insecurity, and it’s 10xed by their exposure.

But I also think they’re wrong.

The historical pattern of these exact predictions failing repeats over and over again.

And it’s both incredibly hubristic and ridiculously short-sighted to think our current viral predictions won’t fail in the same way.

Read more