🍕 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 product, brand, and GTM lab.

You can buy my book Permissionless here.

When did our entire intellectual culture become centered around rearranging and reconfiguring our beliefs, our books, our content, and our ideas to fit a laundry list of accepted, popular, and orthodox concepts we already agree with?

We celebrate every book that comes out, as long as it confirms what we’re already prepared to defend, with all the same citations in mildly different forms, by the same authors who circle-jerk their way through the same podcast appearances, trotting out the same throat-clearing and mic-dropping slogans.

We share quotes that are all but identical as if they’re announcing the second coming of Christ. We call it all Very Important Work. The Newsletters, debate shows, and YouTubers all echo a cohesive and wonderfully on-brand message.

This isn’t a new problem, but it’s getting worse.

Agreement is cheap. Challenge is expensive.

You know what’s free?

Cognitively, spiritually, even philosophically, free?

Reading something already confirms your existing worldview, highlights every piece of information in precisely the right format to re-confirm your existing identity, and takes no effort or discomfort, no revision for any mental model. You finish whatever book, whatever blog post, feeling a good deal smarter than you were when you started (because look! There was content, and now it has been consumed!) but nothing has actually happened.

You’re the same person.

You had no reason to change.

Challenging yourself is incredibly uncomfortable - nobody expects training for and running a marathon to leave you feeling as refreshed and relaxed as a hot bath with a glass of Prosecco. Challenging yourself mentally is no different. You have to hold competing thoughts in your head and let them duke and duel it out, and moderate them for all your life’s worth. Most folks aren’t willing to do that.

Which makes the market for comforting, conforming ideas far more lucrative than the market for ideas with a fighting spirit.

Publishers and Podcast hosts already know this - of course they do. The data tells them everything they need to know about what their readers want. The twelve viral thinkers who all occupy the top slots on every list, from Spotify to the New York Times, know it too. You don’t build your audience by making your audience feel like they’ve got some bloody hard work to do; you build an audience by making people feel like they’re already a murder of geniuses, and by flattering their existing positions. All you really have to do is give them more interesting language for the arguments they’re accustomed to, maybe find a few statistics they can trot out at their next dinner party, maybe give them some soundbites they can quote until they believe they’ve thought of them themselves.

The result is an intellectual ecosystem that looks productive and produces f**k all.

The citation shell game

It’s a problem of both ideology and methodology. The vast majority of the nonfiction genre is just previously published and lauded authors taking an obscure finding from behavioral economics, spinning up a narrative wrapper, finding tangentially related papers for the endnotes, and slapping on a one-word title. And the findings, the book, and the data might not be wrong! It might even be 100%, unarguably on the money! It’s just that it’s the same insights every field has been circulating for fifteen years in a monetizable package sold via an Airport Bookstore.

The citations give it a rigorous cover, which gives the readers the sensation that they’ve encountered and weighed up the evidence, but the narratives are always stronger than the p-hacked data they contain, and every contentious point is hedged, qualified, contested and pruned, and the resulting product is too clean to give anyone an experience that actually changes their lives.

The same twelve people

Every intellectual community has its rotation. The same names show up in the same places and in the same conversations, reinforcing each other’s frameworks and cross-promoting each other’s books.

It looks like a bunch of high-minded conversations.

It looks like whatever festival of dangerous ideas.

It’s more like a mutual admiration society that has figured out how to get paid.

The rotation doesn’t have to be conspiratorial, or the product of a shadowy network of robed freemasons.

It’s just network effects doing what network effects always do. The people who get booked are the ones who’ve been booked before, the people who get cited are the ones who’ve already been cited, and the ideas that get amplified are the ones that fit the community's existing vocabulary.

This produces an intellectual monoculture. The community develops shared assumptions, shared methods, shared standards of what counts as a serious argument – and then those assumptions, methods, and standards become invisible because nobody inside the rotation is pushing back on them.

The people who do push back tend not to get invited back.

I should know. I’m one of ‘em.

What this costs us

The obvious cost is that we stop learning things. If every book is a confirmation of something we already believe, and every podcast is a conversation between people who fundamentally agree, then the actual movement of ideas slows down. We get better at defending existing positions and worse at changing our minds.

We lose the ability to distinguish between knowing something and having a sophisticated vocabulary for talking about it. Smart people in intellectual monocultures become very good at sounding certain. They learn the moves – the citations, the hedges, the casual references to the right thinkers. They develop fluency in their community's dialect.

And fluency starts to feel like understanding, because it works in every conversation they’re part of.

This is how communities of genuinely intelligent people end up systematically wrong about things for a long time.

The way out is uncomfortable

The obvious answer is to read people you disagree with. That’s true but insufficient, because most people who think they’re doing this are actually reading the version of the opposing view that their community has already refuted. The strawman tour. The more useful practice is to look for the strongest version of a challenge to your existing framework, find the smartest person who holds it, and take seriously the possibility that they might be right and you might be wrong.

Most intellectual communities are not set up to reward this. They’re set up to reward the defense of shared positions. Changing your mind on something important is more likely to cost you status than gain it.

So the circle jerk continues. The same twelve thinkers, the same citation layer, the same books that make us feel smarter than we were.

And every now and then, someone will write a piece pointing this out – and it will be widely shared among people who already agree with it.

Including, possibly, this one.

🍕 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 product, brand, and GTM lab.

You can buy my book Permissionless here.

“Good manners are made up of petty sacrifices.”
— Ralph Waldo Emerson

The point of having good manners isn’t to honor an arbitrary ritual; it’s to show a modicum of respect to the folks you come into contact with every day of your life.

We are - as George Costanza would unhappily tell you - living in a society.

No matter how much certain corners of the internet might complain about respectability politics and insist that they’re specially anointed creatures to whom social expectations cannot possibly apply, there is a basic level of decency that we have to agree on.

We need a baseline that acknowledges a simple moral fact: that other people are actually real people. They have inner lives you can’t and don’t get to see; they have sentience, no matter how inconvenient that might be. You don’t get to treat them as disposable, you don’t get to process them into content, and you don’t get to claim their time, publish their flaws, or distribute their worst moments at will.

Technology didn’t create selfishness, but it has made selfish acts extraordinarily easy and almost inconsequential. It’s easier than ever to treat a friend as an audience, use a stranger for content, present a private moment as evidence, feed a human voice into a training set, and turn somebody else’s misfortune into afternoon entertainment.

Attention

1. Write to the people you love in your own voice, not OpenAI’s.

Don’t outsource intimacy to ChatGPT or any other tool.

A clumsy message from you means more than immaculate copy generated on your behalf. The people who love you aren’t waiting for polished prose. They want evidence that you were present. If you’re fighting with your spouse, fight with them. Have some skin in the game. If you’re confronting someone who’s fucked up, confront them; don’t hide behind a chat output.

AI has its place.

That place is not in a 3 AM text conversation with someone who thinks there’s a human being on the other end.

2. Remove your headphones when another person enters the interaction.

If you’re ordering a coffee, take out your AirPods.

Show the person taking your order that you don’t see them as disposable.

I posted this on Threads, and a huge number of people were wonderfully offended by the notion that they should have to inconvenience themselves for even a second to remove a listening device and show the person in front of them that they see them as human.

But nobody should have to compete with a podcast for proof of their existence. Same goes for phone calls, music, everything else. Even if you take a single AirPod out and see // hear the human in front of you, it counts.

If you use AirPods as a hearing aid, you can literally tell the person you’re speaking to. Indicate that you’re paying attention.

There are solutions here.

(If you want to see them, that is…)

3. Don’t make your convenience somebody else’s administration.

A seven-minute voice note may save you time (of course, writing out a text has now become an impossible ask) but only by taking seven minutes from its recipient.

If your message takes minutes to transcribe, interpret, and excavate, write it clearly or ask whether the recipient has time to listen. And if they don’t, make time to see them yourself. Sit down and have that conversation.

4. Keep your private soundtrack private.

Use headphones for music on the train, TikToks in the waiting room, and phone conversations in the supermarket.

Everyone shares public space, and no single person gets to program it. Your tastes might be refined, but they are not the tastes of every human you interact with. The commons shouldn’t be polluted by the tinny speakers of your smartphone, no matter how interesting it may be to you.

5. Ask before adding someone to a group chat.

A group chat does more than collect contacts. It repeatedly captures people’s attention, often exposes them to strangers, and follows them on a device pressed against their bodies.

Don’t enroll people in small digital societies without their consent. Just ask.

6. A read receipt isn’t a subpoena.

People may open a message and think before answering. They may feel tired, distracted, busy, or unsure of what to say, and they may forget.

Instant delivery doesn’t require anyone to respond immediately. And it doesn’t give you the right to demand their focus and attention every single time you feel the urge to share, ask, or prod. You are not the arbiter of anyone’s time, no matter how powerful your phone might make you feel.

7. When you’re with someone, stay with them.

A phone placed face-up on the table joins every conversation as an unwelcome and uninvited third guest, alert and constantly open to distraction, always ready to outrank the person who came to see you.

Put it away.

Turn it off, for the brief 45 minutes you’ve agreed to devote to someone else over a cup of coffee.

If the world comes to an end inside those 45 minutes, it will find another way to let you know about it.

Privacy

8. If people can’t see the camera, don’t use it.

Smart glasses, the now-confirmed AirPods with cameras, and any other device that obscures a camera - or at least makes it less obvious that you’re using one - are the domain of pure assholes.

Don’t use them.

People deserve to know when someone can turn an interaction into a file and broadcast it to the world. If you can’t commit to not using Meta Ray-Bans or whatever other form they’ve taken this year, at least disclose it. It’s not hard to say, “just so you know, my glasses have the option to record you; if you’d be more comfortable, I can take them off, or you can examine them.”

If that’s too hard of an ask - you shouldn’t be wearing them in the first place.

9. Other people’s children aren’t your content.

Don’t publish a child’s face, personal details, school, routines, or vulnerable moments. Not your child, and not anyone else’s child either.

Adults shouldn’t assemble a public identity for a child who can’t yet understand what “public” means. It’s your job to protect the kids in your life from the panopticon, not host a firesale on their privacy for your own gratification.

Yes, this means the end of parenting influencers.

No, nobody is going to miss ‘em.

10. Don’t screenshot the group chat

Don’t trade somebody’s confidence, anger, affection, or bad joke for social approval. If you don’t like what’s going on in the group chat, you’re welcome to leave. You’re welcome to call it out and burn it down. But sharing screenshots of someone who thought they could trust you probably makes you an asshole.

Are there exceptions? Sure. If the people in your group chat are planning on bombing a Walmart, it’s probably worth capturing some evidence of their malice aforethought. Anything outside of that - deal with it as an adult, don’t share it with the world for clout.

11. Don’t film strangers at their worst.

A person crying on a platform, confused in a shop, or unwell on the street isn’t the opening scene of your next viral post. Or at least, it shouldn’t be.

Help them, find someone who can, or give them space, but don’t convert their distress into proof that you were nearby. Maybe they’re crashing out. Maybe they’re being assholes to the folks in their immediate vicinity. Neither of those things are actually helped by your documentation and livestreaming.

If someone’s committing a crime and you need to capture evidence, go right ahead. That principle applies pretty broadly to all of these rules. But someone being a dick isn’t a crime that needs a global jury; people need to be able to sort their crap out between each other, one to one, as grown-ups.

We used to be able to do that.

Why can’t we do it now?

12. On the subject of disclosure by the way…make it your guiding light for AI, too.

If you use AI - if you’re excited about AI - be honest about it.

Stop hiding it.

Refusing to admit to it is cowardly behavior, and it says you’re ashamed of your workflow, jealous of writers who don’t use AI, and uncomfortable with your own choices.

Either use AI and admit to it, or don’t use AI.

But don’t be defensive and play games with people.

It’s that simple.

I keep a monthly-updated “How I AI” disclosure on my Substack About page for anyone to see.

Being transparent about how I use these tools is non-optional for me.

It’s not a high bar.

13. Aim your surveillance at your own property.

Use doorbells, dashcams, and security systems to protect what you own without documenting your neighbors’ entrances, conversations, and daily routines.

Protecting your property doesn’t give you unlimited jurisdiction over everybody else’s life.

Public Life

14. Don’t let a screen remove your body from the world.

The footpath, doorway, and queue still exist, along with the person trying to walk around you.

You’re more than welcome to focus on a screen, but don’t block the path. Move out of the way.

You wouldn’t stop your car in the middle of a freeway to read a text. Don’t stop in the middle of a footpath either.

15. Don’t join in a punishment because it has attracted a crowd.

An algorithm will regularly show you a stranger and invite you to help destroy them. It will offer one clip, sentence, or accusation, then encourage immediate certainty.

Refuse the pleasure of acting as judge, jury, and eager member of the crowd.

You probably don’t know the whole story, and the crowd certainly won’t know when to stop. Even if it’s all entirely justified, the mob doesn’t need another pitchfork-wielding, pearl-clutching, outraged asshole.

Kierkegaard’s formulation: “The crowd is untruth.” The algorithm has simply given the crowd push notifications.

16. Give credit as a matter of honesty.

Credit the person who created the joke, photograph, argument, report, artwork, or recommendation you share.

“Found online” often means, “Someone made this, and I didn’t consider their identity worth finding.”

Take a few minutes to research where it came from.

You have the time. You know you do.

Put the effort in.

17. Do the small work of civilization.

Return the trolley, clear the table, move your bag from the empty seat, leave the shared kitchen usable, and let people off the train before you board.

People with more convenient lives can more easily neglect these gestures, but they haven’t become obsolete.

Human Things

18. Don’t announce a life that isn’t yours.

You may know about another person’s death, diagnosis, pregnancy, engagement, break-up, or redundancy, but you don’t get to publish the news.

Information can involve you without belonging to you.

Ask yourself - why does it matter so much to you to be the first person who knows? Why does it matter to you, beyond getting attention and having the gratification of other people sharing your announcement?

And isn’t there a higher aspiration than being a rabble-rousing town cryer who’s only paid in likes?

19. Answer human effort with human effort.

When someone offers you grief, courage, love, or vulnerability, don’t answer with generated language to avoid the discomfort of finding your own words.

Write the apology, toast, or condolence card yourself.

Your words can be imperfect.

That’s allowed.

Encouraged, even.

20. Allow people to leave their former selves behind.

The internet preserves old material by default, while human beings survive because they can change.

Don’t excavate an old photograph, abandoned opinion, or decade-old mistake merely because a search engine preserved it. Hold people accountable with context and proportion, and allow them to become someone better.

Don’t turn a permanent record into a permanent sentence.

Remember: cancel culture is fairly pointless, at the best of times. It’s even more pointless if you won’t offer anyone a chance at redemption.

21. Never forget the nervous system.

Every account ends in a human body.

The person in the photograph can feel humiliation. The person behind the username may shake while reading your words. The person in the viral clip must continue living after the crowd grows bored.

Before you record, post, forward, expose, mock, or reply, ask:

Would I do this if the person was actually standing in front of me?

Would I use these words if I could see their face change, take the photograph if they could look into the lens, or press send if I had to remain in the room?

As Kant put it - “Man alone… is an end in himself.”

People are never (or perhaps, should never) be merely a means.

They are not raw material for your content, background characters in your day, obstacles to your convenience, or instruments for your gratification. Their attention is not yours to seize, their privacy is not yours to trade, and their worst moment is not yours to publish. Every rule here comes back to that one fact: other people do not exist for your use. They exist for themselves. Act accordingly.

🍕 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 …

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🍕 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.

Productivity systems are mostly built around the same basic assumption: that you are an intellectual delinquent.

Your productivity sucks because, really, you suck. If you’re drowning, it’s your fault and your fault alone. You are failing to track your work, manage your knowledge, and garden your ideas.

It’s a human problem, and you’re the human, so it’s your f**king problem.

The solution for almost every stack is to give you a better inbox and a smarter database, a richer capture system, and more tags. The pressure, of course, is still on you. You have to maintain a second brain and a third dashboard, and you have to become more responsible for the growing stack that now surfaces everything, and makes every scrap feel like something you owe a response to.

Epictetus was a freed slave who used a rented room as his classroom, where he taught philosophy and shaped an almost embarrassing amount of modern thought.

And the poor blighter did it without Obsidian, without a PKM, and without any AI agent to manage his second brain (bad luck). He didn’t even believe that capture itself was the right problem; his system started instead with a simple question.

What is yours to manage?

Epictetus focused on three things: your judgments, your desires, and your decisions; in particular, he emphasized choosing what to pursue, what to turn down, what to keep, and what to cut out completely.

Everything outside that circle is neither your circus nor your monkeys.

Everyone else’s actions, opinions, ideas, annoyances, traumas, outrages, and emotional dysregulation don’t actually need to concern you at all. Neither do the various algorithms you can’t reshape or the markets you can neither predict nor control, or the emails someone else marked urgent based on their needs and their deadlines. None of these things belong to you, and it’s not your job to try to own them.

The Stoics called this the dichotomy of control; the YouTube philosopher squad might call it a lifehack. I call it a damn good way to avoid going insane while still getting through a to-do list.

What the Apps Are Selling

Apps like Notion, Obsidian, Linear, and Todoist, as well as every version of GTD, are designed to solve logistical problems. They assume everything that comes your way is important and help you process it faster. If a colleague’s project is off track and you receive an email, the system helps you capture, prioritize, and respond. If your manager asks for a status update on Slack, the tool helps you find the right information. The idea behind all these features is that you should manage everything that comes your way.

Epictetus disagrees at the premise level. The email, the notification, the project that isn’t yours but has somehow been made to feel like yours: these are weather. You can dress for weather. You can decide whether to go outside. But you still don’t control the weather; you decide your response to it, but tracking it carefully doesn’t give you control. It gives you a more detailed picture of something that was never in your jurisdiction.

The issue with capture systems is that capturing something makes it yours. When you write something down, you’re accepting it as your responsibility.

You turn it from just background noise into a task.

By capturing it, you’re agreeing to handle it.

The Filter He Built

Before you track something, you ask, “Is this mine?”

Does it fall inside my jurisdiction, meaning my judgments and my actions?

If yes, it enters the system.

If no, you don’t capture it, you don’t feel bad about not capturing it, and you don’t build a project called “deal with this somehow” that sits in your review list for eleven weeks.

Modern work is organized to continuously blur this boundary.

Your inbox is someone else’s output queue. Your task list is partly your goals and partly other people’s requests, and the system doesn’t distinguish between them. A good project management tool will surface every dependency, every blocker, and every nagging worry, every performative tweak and “I Wonder If” - because the tool’s implicit theory is that awareness equals capability. If you can see it, you can address it, so you should address it.

Epictetus built his system under conditions where the most important facts of his external life were beyond any influence he could exercise: his legal status, his owner’s decisions, the terms under which he worked and lived. He couldn’t productivity-hack his way to freedom; the levers weren’t his to pull. The only domain he owned was internal: what he chose to pursue, what he refused to want, how he interpreted his situation.

Most people mistake the number of things coming at them for the number of things they’re actually responsible for.

These are not the same.

But the apps don’t make that clear.

What You’re Actually Responsible For

In Epictetus’s system, you’re responsible for what you agree to, what you refuse, and the actions that come from those choices. When you get a message, you decide if it needs your response or if it’s something that will sort itself out (or not, but it’s still not yours). If it’s yours, you respond. If not, you don’t track it, save it for later, or add it to a maybe list. You just move on.

This sounds like negligence from the outside. If you’re a senior engineer and a colleague’s architecture decision will create downstream problems, surely you should track it, flag it, follow up. Epictetus would draw a sharper line. Your judgment that the decision is wrong: that’s yours, and you act on it once, clearly, directly. Their decision about what to do with your input: that’s theirs.

You could call this the Jurisdiction Method. Before you decide to track something, ask: whose responsibility is this? If it’s yours, take action. If it belongs to someone else, you might influence it, but you don’t own it, and you shouldn’t let it take over your attention just because you’re tracking it.

The reason this system outperforms the apps has nothing to do with throughput efficiency. You’ll probably respond to fewer things. You’ll miss some status updates you were meant to have seen. You’ll decline some requests that could have been met.

All of these are a worthy tradeoff for a defensible boundary around what failure means. You failed if you acted against your own judgment. You failed if you refused to engage when engagement was genuinely yours to give.

You didn’t fail because someone else’s project slipped, or because the algorithm deprioritized your content, or because the market moved in a direction you couldn’t predict.

Most people feel “behind” because they’ve taken on responsibility for things that were never theirs.

If that describes you, you should be asking:

Is this mine?

If it is, you know what to do.

If it isn’t, no system in the world will make the doing easier.

🍕 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 th…

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🍕 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 th…

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🍕 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…

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Chapters

• 00:00 — How Starbucks became a coffee com…

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🍕 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…

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🍕 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 …

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🍕 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 th…

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🍕 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.

“Content creation” was always going to trend toward the factory model.

Anyone paying attention could already see it happening in the 2010s, when SEO slop farms started crowding out the internet with piles of nonsense and bullshit.

But back then, human writers were still the norm, and the stock standard advice for most of us was to publish 1000-2000 word blog posts. It was the best way to capture your ideas, it was the best length to hook an audience, and it seemed to represent an enormous gift of value to the reader.

Long = good.

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🍕 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 …

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🍕 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 …

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🍕 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 th…

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🍕 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…

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🍕 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.

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🍕 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.

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🍕 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 …

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🍕 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…

Read more