I spent most of my twenties believing that purpose was something you found once and then held onto.

A winning lottery ticket you kept in your wallet forever.

The self-help industry reinforced this: find your passion. Discover your why. Land on the thing that makes you leap out of bed every morning and then, presumably, keep leaping until you die.

Nobody ever mentioned that some mornings I might not feel like leaping at all, and that this would be fine, even normal, even healthy.

The idea of seasonality shows up in every religious tradition, every folk wisdom corpus, every grandmother's hand-me-down advice, emblazoned on a hundred hallmark greeting cards - and yet we somehow keep forgetting it applies to us.

We accept that crops grow and then get harvested and then the field lies fallow.

We accept that animals hibernate.

We accept that the world needs rest periods built into its operating system.

But when it comes to our own sense of meaning and purpose, our work, our lives, we expect constant summer.

Anything less feels like failure.

I've noticed, looking back over the past decade, that my periods of intense creative output followed a pattern I couldn't see while I was inside them.

There were stretches where I wrote feverishly, where ideas connected to other ideas in chains that felt almost involuntary, where I would wake up at 4 AM with sentences already forming, where (simply put) the work felt effortless.

And then there were long months where I would sit at my desk and feel nothing.

I assumed something had broken. I tried to fix it. I read books about productivity. I adjusted my routines. I wondered if I had permanently lost access to whatever had driven me.

What I failed to notice: that the fallow periods were doing something too. They were composting. I was taking in books and conversations and experiences without the pressure to immediately metabolize them into output. I was wandering without a map, which meant I sometimes stumbled into territory I never would have found if I'd been navigating by GPS.

The harvest seasons, when they returned, drew on seeds I hadn't remembered planting.

There's something cruel in how our culture treats the in-between times. We have words for achievement and words for burnout, but we lack vocabulary for the necessary pauses that precede new growth. If you tell someone you're "taking a break," they hear that you're recovering from something bad. If you say you're "between projects," they assume you've been cast aside. The idea that you might be in a natural winter, that you might be dormant in a way that's preparatory rather than pathological, doesn't compute for most people.

I think part of the problem is that we've internalized an industrial model of human output. Factories don't have seasons. They run continuously, and when they stop, something has gone wrong. We've mapped this onto ourselves without asking whether the analogy holds.

But humans are not factories.

We are, as obvious as this may seem, organisms.

And organisms live through cycles.

I've started asking people about their seasons, and the responses are illuminating. Almost everyone recognizes the pattern once you name it. Almost everyone has experienced multiple cycles of engagement and withdrawal, of burning purpose and comfortable drift. And almost everyone has interpreted at least one of their fallow periods as evidence of something being wrong with them specifically, rather than as a feature of how human lives actually work.

You can look at a calendar and know roughly when winter will arrive. Human seasons are messier.

Sometimes summer lasts three years.

Sometimes winter arrives without warning in the middle of what you thought was spring.

Or in the middle of the night.

Sometimes you're in winter for one domain of your life and summer for another simultaneously, which creates its own kind of confusion.

But the unpredictability doesn't invalidate the pattern. It just means you have to pay attention to your own internal weather instead of relying on external schedules. There are signs, if you're watching for them. A creeping restlessness that suggests you're ready to plant something new. A bone-deep fatigue that suggests you need to stop harvesting and let the field recover.

The self-help industry will keep telling you to find your passion and hold onto it. The productivity gurus will keep implying that consistent output is the hallmark of a well-lived life. And every winter, when your sense of purpose goes quiet, you'll be tempted to believe that you've done something wrong.

You haven't. You're just in a season. Don't try to force a harvest when the ground is asking you to rest.

I have been through winters before and I have always, eventually, found my way back to spring. The springs didn't come because I forced them or fixed myself or followed a twelve-step program. They came because seasons end. They came because the resting period did its hidden work. They came because, whether I knew it or not, I was gathering in the dark.

We talk about making decisions as if they're binary switches.

You choose A or you choose B, and the main thing you've spent is the possibility of choosing the other option.

But anyone who has spent an afternoon researching which standing desk to buy, only to realize they've burned four hours on what amounts to a $200 purchase, knows that decisions cost us more than just the paths not taken. They consume multiple resources simultaneously, and we rarely account for all of them when we're in the thick of choosing...

Every decision extracts payment in three distinct currencies: time, focus, and optionality.

Understanding these costs separately helps explain why some choices feel exhausting even when they're objectively trivial, and why people who seem to make worse decisions sometimes end up happier than those who agonize over optimization.

The time cost seems obvious enough.

Deciding takes clock time.

You research options, compare features, read reviews, maybe make a spreadsheet. If you're buying a car, you might spend weeks on this process. If you're choosing a health insurance plan, the research phase alone could consume dozens of hours.

But the time costs compound with the stakes of the decision itself.

A $30,000 car purchase might warrant significant research time.

But the typical person spends almost as much time researching a $600 smartphone, even though the financial impact is far smaller.

Aka: we're terrible at calibrating our time investment to the actual magnitude of what we're deciding.

The arithmetic gets worse when you consider recurring decisions.

Choosing where to eat lunch every workday looks trivial in isolation, but if you spend fifteen minutes deciding each time, you've spent more than sixty hours per year just picking restaurants.

Some solve this by establishing defaults or routines.

Others treat each occurrence as a fresh decision, paying the time tax repeatedly.

Neither approach is obviously wrong, but most people drift into their pattern without consciously choosing it.

Focus costs are harder to measure // more expensive. Making decisions depletes a mental resource that doesn't replenish instantly. This is why you can spend a Saturday morning researching laptops and find yourself unable to write a clear email that afternoon, even though writing emails is normally trivial for you.

The mental motion of weighing alternatives, projecting future scenarios, and committing to a choice draws from the same well that powers your other cognitive work.

Compounding the focus cost: decisions create background radiation while they're pending. An unmade choice sits in your mental workspace, occasionally pinging you with anxiety or drawing cycles of rumination. You might think you're working on something else, but part of your brain keeps returning to the decision, running simulations, reconsidering options.

This is why solving even a minor pending decision creates a disproportionate sense of relief: you're reclaiming the cognitive territory that decision was occupying.

People who maintain long (even subconscious) lists of pending decisions wonder why they feel perpetually scattered or can't concentrate on difficult work. The answer might be that they're trying to run their mental processes while carrying too many open threads. Each unmade choice is a program running in the background, consuming resources even when you're not consciously thinking about it.

The optionality cost is the most subtle and probably the most significant. Every decision forecloses some possible futures and narrows your path forward. This is obvious with big choices like career moves or relationships, but it applies to smaller decisions too. When you schedule a meeting, you're eliminating all the other things you could do in that time slot. When you commit to learning Spanish, you're implicitly not learning Japanese, at least not simultaneously.

That optionality has diminishing returns. Having infinite options sounds appealing in theory, but in practice, it becomes paralyzing. The person who keeps all their evenings free has maximum optionality but often ends up doing nothing memorable with that freedom. Meanwhile, someone who commits to a standing weekly dinner with friends has traded optionality for consistency and depth.

Which is better?

The answer depends entirely on what you value and where you are in life.

Some decisions are reversible, which makes their optionality cost lower. You can quit a job, move to a new city, or switch insurance plans. But reversibility itself comes with costs. The mental overhead of maintaining the option to reverse a choice can be as draining as making the original decision. People who constantly re-evaluate whether they're in the right relationship or living in the right place pay ongoing focus costs for that perpetual reconsideration.

Some folks systematically undervalue one of these costs relative to the others. The person who spends weeks researching a minor purchase is overweighting time to preserve optionality. The person who makes snap judgments on important matters is preserving time and focus but might be squandering optionality. The person who agonizes endlessly over every choice without committing is burning focus to maintain optionality they'll never actually use.

The “righteous path” (if there is such a thing) probably involves a degree of conscious triage, no matter how painful.

Identify which decisions actually matter for your goals and values, then allocate your three currencies accordingly. For decisions that don't matter much, minimize time and focus costs even if that means accepting suboptimal outcomes or reduced optionality. For decisions that do matter, invest whatever combination of time, focus, and optionality the choice genuinely warrants.

But of course - most of us are bad at this triage. We spend enormous cognitive resources on decisions that barely matter while rushing through choices with genuine long-term consequences. We optimize our coffee order while sleepwalking into careers. We research consumer products exhaustively while barely examining our underlying assumptions about what makes life good.

The person who learns to make trivial decisions quickly, save their focus for what matters, and consciously choose which optionality to preserve will probably end up both more productive and more satisfied than the person who treats every choice as equally weighty.

You can't optimize everything.

Which decisions are worth the three-currency investment, and which ones are you better off resolving with a coin flip?

Here’s a thought experiment you’ll come across on social media:

Imagine your 80-year-old self looking back at the day you're having right now.

What would they give to inhabit your body again, to have your knees that don't ache, your schedule that seems so overwhelmingly full, your problems that feel so urgent?

Like most self-help advice, there’s a kernel of psychological insight here + several layers of motivated reasoning.

But unlike most self-help advice, the core mechanism actually checks out when you look at what we know about how humans experience time, value, and regret.

Start with the empirical observation that people's biggest regrets tend to cluster around inaction rather than action. When psychologists survey people about their life regrets, they find a consistent pattern: in the short term, people regret things they did. In the long term, people regret things they didn't do. The embarrassing thing you said at the party haunts you for weeks. The career you never pursued, the relationship you never tried to fix, the year abroad you never took - these haunt you for decades.

This makes sense if you understand how memory and emotion interact over time. Psychologists call it the "fading affect bias" - the emotional intensity of negative memories decays faster than positive ones. The mortifying moment loses its sting. The road not taken becomes more vivid, more tantalizing, precisely because it never happened. Your imagination fills in all the blanks with the best possible outcomes, while your actual experiences get remembered with all their messy complications intact.

We have an overwhelming tendency to value future rewards less than immediate ones, and conversely, to value past experiences less than current ones. When you're 25 and your back hurts after moving furniture, you don't think "thank god I can still move furniture." When you're 80 and can't move furniture, you remember when you could and the memory has a different texture entirely.

We have pretty good data on what actually happens to people's subjective wellbeing as they age. The U-shaped curve of happiness is one of the most robust findings in social science: people report being happiest in their twenties, hit a low point somewhere in their forties or fifties, and then happiness increases again in later life. The interpretation of this finding is contested - are older people actually happier or just better at regulating their emotions? Do they compare themselves to worse alternatives or have they genuinely figured something out?

Whatever the mechanism, older people consistently report higher life satisfaction than middle-aged people, which complicates the simple narrative that your 80-year-old self is sitting around in wistful jealousy of your younger incarnation. Laura Carstensen's socioemotional selectivity theory suggests that as people's time horizons shrink, they shift their priorities toward emotional satisfaction and away from future-oriented goals. Old people aren't necessarily pining for youth; they're often quite content being old.

Does this mean the thought experiment is useless? Not quite.

Its value is in what it reveals about your current priorities. When you imagine an elderly version of yourself looking back, you're running a sort of values clarification exercise. You're asking which parts of your current life would seem precious from a distance, which anxieties would seem trivial, which opportunities would seem worth taking.

The economist Bryan Caplan talks about "hedonic adaptation" - our tendency to return to a baseline level of happiness after positive or negative events. Win the lottery and within a year you're about as happy as you were before...

We're remarkably bad at predicting what will make us happy because we forget how quickly we adapt to new circumstances.

But hedonic adaptation works in reverse too. We adapt to our current circumstances so thoroughly that we forget they once seemed amazing. The first time you could afford to eat at a nice restaurant whenever you wanted, it felt like luxury. After a few years, it's just dinner. Your first apartment without roommates was a revelation. Now you barely notice it. This is where the 80-year-old perspective becomes genuinely useful - it reminds you that your baseline is extraordinary compared to what many humans throughout history experienced, and compared to what future you might have.

Maybe you can walk up stairs without thinking about it. Maybe you can read for hours without your eyes getting tired. Maybe you can stay up past 9 PM without feeling like you're dying. Maybe people still want to hire you, date you, collaborate with you. Maybe you still have the energy to pursue projects that seem pointless to everyone else. These capabilities have an expiration date, and you probably won't know when they've expired until well after the fact.

Simply knowing this doesn't automatically make you appreciate things more. Gratitude isn't something you can will into existence through rational argument alone. If it were, reading studies about hedonic adaptation would make everyone permanently happy. What the thought experiment actually offers is a frame - a way of seeing your current situation that makes certain features more salient. It's cognitive reappraisal, which is one of the more effective emotion regulation strategies we have.

Does your 80-year-old self really envy the day you're having? Probably not as much as the thought experiment suggests. They might be quite satisfied with their senior citizen discount and their lack of workplace drama. But would they look back on certain days - certain ordinary, unremarkable days - and wish they'd paid more attention? Would they want to tell you something about which worries actually matter and which don't?

Almost certainly yes.

The arbitrage opportunity here is real. You can trade your current anxiety about mundane problems for a “borrowed” perspective that lets you see those problems as they actually are: temporary, survivable, often forgettable. You can recognize that having problems to solve, having energy to worry, having a future to fret about - these are luxuries that won't last forever. The exchange rate between present experience and future memory is almost never in your favor, which means that right now, in this moment, you're probably undervaluing what you have.

You don't need to be grateful for everything.

Some days genuinely suck.

Some problems really matter.

But most days contain at least a few elements that future you would miss, if only you could train yourself to notice them now. The person you'll be in 50 years might not give everything to have today back, but they'd probably give something. The question is whether you can cash in on that future regret now, while you still have time to enjoy the things you'll eventually wish you'd enjoyed more.

Patti Smith said it best:

One of my best mates regrets moving to Austin. The job didn’t work out, the culture wasn't what they expected, and now he’s planning to move back to New York within the next year.

He had an offer for a role that paid 40% more than his New York position, the cost of living was dramatically lower, and he’d been complaining about New York winters for the better part of a decade. The job collapsed because of funding issues that nobody could have predicted. The culture mismatch was real, but how could he have known without trying?

The question he asked me: did he make a bad decision?

We conflate the quality of our decisions with the quality of their outcomes so automatically that we rarely notice we're doing it. A good decision that leads to a bad outcome gets reclassified in our memory as a bad decision. A terrible decision that happens to work out becomes evidence of our brilliant judgment. We are constantly running our own internal kangaroo court, retroactively convicting or acquitting our past selves based solely on how things turned out.

Thinking in bets offers a way out of this trap.

When you frame a decision as a bet, you're forced to explicitly acknowledge that you're operating under uncertainty. You have to assign some probability to different outcomes, however rough. You have to think about expected value rather than guaranteed results. My friend made a bet that had, let's say, a 70% chance of working out well and a 30% chance of not working out. He lost the bet. That doesn't retroactively make it a bad bet.

This might sound like motivated reasoning, a way to excuse bad judgment by claiming "well, it seemed like a good idea at the time." But the difference is that thinking in bets forces you to be honest about what you actually knew at the time versus what you learned afterward. If you claimed there was a 95% chance of success when any reasonable analysis would have suggested 50/50, you made a bad bet regardless of the outcome. If you carefully weighed the probabilities and made the choice that maximized your expected value, you made a good bet even if you got unlucky.

Professional poker players understand this viscerally. You can play a hand perfectly and still lose because someone hit their 8% draw on the river. You can play terribly and win because you got lucky. What separates good players from bad players over the long run is the quality of their betting decisions, not the outcomes of individual hands. Good players lose hands all the time. They just make sure they're making +EV (positive expected value) bets when they do.

Think about how differently we might approach major life decisions if we thought about them probabilistically. Instead of asking "should I take this job?" you'd ask "what's my estimate of this working out well, and given that probability, what's the expected value compared to my alternatives?" You might still take a risky job if it has high enough upside and you have a decent chance of success, even if failure is a real possibility.

When you make a binary decision, admitting you were wrong feels like admitting you're bad at decisions. When you make a probabilistic bet, being wrong just means you were on the losing end of the odds this time. You can simultaneously acknowledge that the outcome was bad while maintaining that the decision was sound.

This has downstream effects on how you learn from experience. If every bad outcome is evidence of bad judgment, you'll be motivated to rationalize or minimize your failures. You'll be reluctant to take reasonable risks because any failure will be counted against you.

But if you can separate decision quality from outcome quality, you can look at your failures more honestly.

You can ask: did I misjudge the probabilities? Did I have information I should have weighted differently? Or did I actually make a good bet that happened not to pay off?

There's a trap here, though.

Isn’t there always…

You can't just assign whatever probabilities make you feel good and then claim you're thinking clearly. The probabilities have to be calibrated to reality, which means tracking your predictions and adjusting when you discover you're systematically over or underconfident. If you keep saying things are 80% likely and they only happen 50% of the time, you're not thinking in bets so much as you're using probability as a fig leaf for wishful thinking.

When you apply this consistently over time, you start noticing patterns in the types of bets you make. Maybe you're too conservative about career moves but too aggressive about financial risks. Maybe you systematically overestimate your ability to finish projects quickly. These patterns are much harder to see when you're thinking in binary terms, where every decision is either vindicated or condemned by its outcome.

Some people resist thinking this way because it feels cold or calculating. Where's the room for intuition, for gut feelings, for the ineffable sense that something is right? But probabilistic thinking doesn't exclude intuition. Your intuition is providing you with information, you're just being more honest about the uncertainty inherent in that information. When something feels right, you might update your probability estimate upward. You're just not pretending that your intuition provides certainty when it doesn't.

Others worry that thinking in bets will paralyze them with overthinking. If you have to calculate expected values for every decision, won't you waste enormous amounts of time on analysis? But you can think in bets at whatever level of precision the decision warrants. Choosing where to get lunch doesn't require a spreadsheet. Choosing whether to go to graduate school might benefit from one. The framework scales to the stakes.

What happens when you extend this thinking to your beliefs more generally, beyond just decisions? You start saying things like "I'm about 60% confident that" instead of making definitive pronouncements. You become more comfortable with uncertainty. You can hold multiple contradictory hypotheses in your mind simultaneously, weighted by probability. When new evidence comes in, you update your probabilities rather than either ignoring the evidence or completely reversing your position.

The world contains more uncertainty than we're comfortable acknowledging. We want to believe that if we just think hard enough, gather enough information, and make the right choice, we can ensure success. We want to believe that good decision-making guarantees good outcomes. But it doesn't. Sometimes you make the best possible choice given the information available and things still go sideways. Sometimes you make a questionable choice and get lucky.

Thinking in bets lets you make peace with that uncertainty without surrendering to fatalism. You can take responsibility for the quality of your decisions while acknowledging that outcomes are probabilistic. You can learn from your failures without assuming that every failure represents a personal deficiency. You can take reasonable risks without being paralyzed by the possibility of loss.

My mate made a reasonable bet that didn't pay off. He’s not stupid for having moved, and he’s not stupid for moving back. He gathered information, updated his probabilities, and made a new bet based on what he learned. That's exactly what thinking in bets looks like in practice. It's messy, it involves backtracking, and it doesn't guarantee success.

But it gives you a fighting chance of making good decisions in a world that refuses to offer you certainty.

Somewhere around 2016, the smartest people I knew started saying increasingly stupid things.

These were folks who could parse dense academic papers, who understood reason, who were entirely capable of holding two competing ideas in their heads without their brains short-circuiting.

But something changed.

One friend became “convinced” that every major news story was manufactured consent. Another started treating political disagreement as evidence of moral corruption. A third began using the word "liberal" as if it was a personality disorder rather than loose coalitions of sometimes contradictory beliefs.

The common thread: their extreme positions got them more of what they wanted. The friend who saw conspiracies everywhere built a following. Then an audience. Then a 7-figure income stream. The one who tribalized every issue found a ready-made community that validated every prior. Etc, etc.

The incentive gradient was clear: sanity was expensive, and extremism paid dividends.

We talk a lot about polarization as if it were a disease that infected society, but we’re missing a key data point: polarization is a growth hack, and it works.

It delivers results.

When you pick a side and commit to it wholly and without reservation, you get things that moderate positions cannot provide. You get certainty in an uncertain world. You get a community that will defend you. You get a simple heuristic for navigating complex issues.

Above all: you get engagement, attention and influence.

The writer who says "this issue has nuance and I can see valid concerns on multiple sides" gets a pat on the head and zero retweets. The influencer who says "everyone who disagrees with me on this is either evil or stupid" gets quote-tweeted into visibility and gains followers who appreciate their approximation of clarity.

The returns on reasonableness have almost entirely collapsed.

Which begs the question: why resist? If extremism delivers what people want, maybe we should just let it run its course and stop clutching our pearls?

The problem is what happens when everyone optimizes for the same short-term wins.

You end up in a world where changing your mind becomes impossible because you've built your entire identity around being right. Where admitting uncertainty is social suicide. Where every conversation is a performance for your tribe rather than an actual exchange of ideas. You lose the ability to solve problems that don't fit neatly into your ideological framework, which turns out to be most important problems.

Someone who goes all-in on ideological purity might start with a few strong opinions. Then those opinions attract an audience. That audience expects consistency. Any deviation gets punished. So they double down. They have to keep escalating to maintain their position, finding new heresies to denounce, new lines to draw. They've locked themselves into a trajectory they can't escape without losing everything they've built.

They're prisoners of their own brand.

Scale this up and you get a society where nobody can back down, where every disagreement = existential, where we've lost the ability to make tradeoffs // acknowledge complexity.

The incentives push us toward positions that feel good but make us collectively stupider.

And you can't opt out by just accepting your side lost.

You're stuck in stupid-world too.

So how do you actually stay sane?

1. Start by diversifying your information diet in ways that feel actively uncomfortable. The goal isn't to agree with everything you read. You'll still think most of it is wrong. But exposing yourself to articulate versions of positions you oppose does something valuable: it makes you realize that intelligent people can disagree with you without being monsters or morons. This sounds obvious when written out, but your social media feed has spent years training you to believe otherwise.

2. Second, practice distinguishing between stakes and truth. Just because an issue matters doesn't mean every claim about it is correct, and just because you've picked a side doesn't mean you have to defend every argument your side makes. The tribal logic says you have to accept the whole package, but that logic is selling you certainty you haven't earned.

3. Third, find (or at least, look for) communities that reward humility, not tribal loyalty. These are rare, but they exist. They're the group chats where someone can say "I changed my mind about this" without being treated like a traitor. They're the forums where "I don't know" is an acceptable answer. They're the relationships where you can test ideas without performing for an audience. You cannot be reasonable in isolation. You need a small group of people who value truth-seeking over status games, and you need to invest in those relationships deliberately.

That all sounds hard.

Is it worth it?

That’s an individual choice.

You'll lose: reach, influence, certainty, the comfort of being part of something larger than yourself.

You'll gain: the ability to think clearly, the capacity to update your beliefs when evidence changes, relationships based on something other than shared enemies, and the possibility of being right in ways that matter.

These trades won't feel equivalent. The losses are immediate and visceral. The gains are distant and abstract. When you refuse to join the mob, you feel it right away. When you maintain your ability to think independently, the benefits accrue slowly over years.

The discount rate on sanity is brutal.

But consider the alternative.

The people I knew who went all-in on extremism got what they wanted in the short term. Some built audiences. Some found communities. Some gained certainty. Most of ‘em made bank. But they're trapped by their earlier positions. They can't update without admitting they were wrong, and admitting they were wrong would cost them their community. They've optimized themselves into a local maximum they can't escape. They won the game by its current rules and lost something harder to quantify.

The world will keep offering you bad trades, will keep rewarding positions you know are too simple to be true. Every day you'll watch people cash in their nuance for influence. Every day you'll be tempted to do the same. The only defense is to remember that some things compound differently than others.

Extremism gives you a fast start and a ceiling.

Sanity gives you a slow start and no limit to how far you can grow.

Remember: the world only rewards insanity because we're measuring the wrong timeframe.

Check back in ten years.

There's a genre of thought experiment that involves writing letters to your younger self.

You're supposed to impart hard-won wisdom, spare your past self some suffering, maybe tell them to buy Bitcoin or avoid that regrettable haircut.

I've been thinking about what I'd write in such a letter, and I've concluded the whole exercise is doomed from the start.

My younger self wouldn't listen.

Worse, if they did listen, they’d undoubtedly fuck it up in some other // alternative // novel and creative way I can't even anticipate.

The problem with advice-giving in general is that nobody takes advice. Your mate asks whether they should break up with their mediocre boyfriend, you give them a thoughtful analysis of their relationship dynamics, and three months later they're still together and complaining about the same things.

But the Blogosphere’s favourite “letters to younger selves” genre has a special kind of futility baked in.

You're not just battling human nature's foundational resistance to advice. You're fighting the specific human nature of the person you used to be. And that is futility itself.

This is me: I was anxious in ways that made perfect sense to me at the time and seem completely insane now. I cared desperately about things that turned out not to matter at all, and dismissed as unimportant the exact things that would shape my entire adult life.

If I wrote to tell my eighteen-year-old self "that philosophy class you're dreading will change your entire worldview, and that party you're excited about will be completely forgettable," they’d probably think I was lying or had become boring with age. They’d go to the party anyway, skip the reading, and feel vaguely guilty about both.

The advice that would actually be useful is the advice I couldn't have followed. "Learn to notice when you're optimizing for looking smart rather than being correct" is great counsel, but it presupposes a level of awareness that took me years to develop. Younger me was a glorious, wondrous idiot. Younger me wouldn't have even understood what I meant. They’d have nodded, thought they understood, and continued doing the exact thing I was warning against, now with the added confidence that they’d already learned the requisite lesson.

Fact: You can't skip steps.

You need a certain amount of accumulated experience, mistakes, and random encounters with ideas before new concepts can slot into place. Telling my past self to read certain books at the wrong time would be like trying to teach calculus to someone who hasn't learned algebra yet. The information would bounce off. Worse, premature exposure might have inoculated me against ideas I'd later need. I've seen people encounter ideas far too early, decide they've understood them, and then walk around with a cargo cult version that makes them more wrong than if they'd never heard encountered the concept in the first place. See: people who think they understand 1984, Marxism, capitalism and human behaviour at the salad bar.

And then there's the problem of specificity versus actionability. The advice that's specific enough to be useful ("don't date *Anna, it will end badly") creates weird paradoxes. If I don't date *Anna, do I still become the person who would later write this letter? The advice that's general enough to be robust ("be more honest with yourself about what you want") is functionally no different to a Hallmark platitude that everyone already knows and nobody knows how to implement.

Younger me had probably already heard some version of every useful thing I could tell them. The problem was never information. The problem was that knowing things intellectually and actually integrating them into your decision-making are completely different processes.

I think about the Litany of Tarski sometimes: "If the sky is blue, I desire to believe that the sky is blue. If the sky is not blue, I desire to believe that the sky is not blue."

Eighteen-year-old me could have recited this perfectly while simultaneously and convincingly lying about whether they actually enjoyed their major, whether their friends were good for them, whether their study habits were working. The gap between knowing a principle and living by it can be...enormous.

Would I tell my younger self about my current life?

That seems like it might work, at least as motivation. "Look, everything turns out fine! You get the things you want!" But I'm not sure that's even true in the way younger me would have understood it. I got things, sure, but not the specific things I thought I wanted. I wanted to be impressive in ways that now seem silly to me, and I accidentally became decent at things I hadn't even considered pursuing. If I described my actual life to my younger self, they might be disappointed. They’d focus on the things I didn't achieve and miss the things I value now that weren't even on the radar.

Here's what I suspect would actually happen if I could send a letter back: I'd agonize over what to say, write something carefully calibrated and wise, and my younger self would read it with mild interest, think "yeah, yeah, I get it," and then continue making exactly the mistakes I made. Maybe they’d have a few new anxieties about whether he was making those mistakes. Maybe they’d overcorrect in some direction that creates different problems.

The only advice that might work is the advice they were already halfway to figuring out. If I caught them at exactly the right moment, when they were already starting to question something, then a letter might accelerate that process by a few months. But the big realizations, the fundamental shifts in perspective, those seem to require their own timeline.

They need to be earned.

To some degree, they need to hurt.

What would I write? Probably something like this: "You're going to be fine. The things you're worried about mostly won't matter. The things that will matter, you can't predict yet. Try to be kind to people, including yourself. Pay attention to what you're actually experiencing rather than what you think you should be experiencing. Good luck. You won't take this advice, but that's okay. You'll figure it out eventually."

Then again, the whole point of the exercise is to feel like you've learned something, to convince yourself that you're now wise enough to give your younger self advice.

The letter is less about the advice and more about the distance. Look how far I've come. Look at all the things I understand now. The younger self who wouldn't listen is proof that I've grown.

Which is fine, I suppose.

We all need our little rituals of self-reassurance.

Today I'm talking to Ken Case, founder and CEO of Omni Group, the makers of some of my favorite productivity software tools that I've been using for quite a long time on my Mac and iPad. We're going to be talking about productivity techniques, tools, ideas, and philosophies.

Links

Testing the next OmniOutliner - The Omni Group

Great things often begin as outlines. Whether you're a writer or a student, an attorney or a software developer, outlines can help clarify and develop ideas and concepts. We're thrilled to share that the next version of OmniOutliner is nearly ready as a universal app for Mac, iPad, iPhone, and Apple Vision Pro, and that we're making test builds available to anyone who wants to help make sure we haven't overlooked anything.

www.omnigroup.com/blog/testing-the-next-omnioutliner

Task Management Software Built For Pros - OmniFocus - The Omni Group

Task management software for busy professionals that helps them accomplish more every day.

www.omnigroup.com/omnifocus

OmniWeb test builds

omnistaging.omnigroup.com/omniweb/?pk_vid=015ecab7a59d2ef0176246291544fe6f

Ken, it's awesome to have you.

Ken Case: Thank you for inviting me. It's fun to be here.

The Early Days

You've been working on Omni Group for a long time, longer than most of the productivity tools that people are using today. Is that fair to say?

KC: That is fair to say—longer than some of our employees have been alive.

What year did you start Omni Group?

KC: The founding date I look at would be 1992, which is the year that we registered omnigroup.com. We had been working together as consultants before that, but we were working on various projects, sometimes together, sometimes not, and we were always getting paid by somebody else directly. 1992 is when we decided to make this a common endeavor and move forward that way.

It feels like the classic pipeline from the original days of productivity tools—folks who were building products for other people, getting paid as consultants and developers, who took the leap to create their own products. Do you think that shaped what you were doing at Omni Group?

KC: Yeah. I started seeing a shift in the eighties, really, between one set of philosophies where people were just using computers for fun and for productivity because of their passion for it, to "oh, maybe people can make money out of this." We got a lot more business majors starting to take computer classes in the eighties than just computer folks who were these odd geeks off in the corner.

But by trying to ground yourself in what people are actually trying to do and solve their specific problems—we started out as a consulting company building custom solutions for different businesses—you really have to listen to what people are trying to do and then think about how you can make that better for them.

Building for Apple Platforms

You've been building for Apple platforms since the NeXT days, is that right?

KC: Yes, if you can count the NeXT days as being part of the Apple platform.

I think we can now, in hindsight. So what is the underlying belief about platform-specific software that keeps you loyal to that path?

KC: When I first encountered the NeXT platform, I was trying to develop software for as broad a range of Unix platforms as possible, because that felt like the best way to get the most value for the effort I was putting in. At that time, there were probably at least 15 different Unix variants that I was building for.

Then I discovered the NeXT platform, which had a very different way of working with AppKit and Objective-C, and I realized I could build much more polished products with a lot less code. That made me more productive with a much more productive result. But of course, you were then stuck to this tiny audience of the NeXT platform, which was not very big at that time.

I thought long and hard about that trade-off and decided I really wanted to be producing the best product I could, even if the audience ended up being smaller. The productivity gains made that worth it. So I focused on what I could do to help that platform grow and succeed so that the audience would get bigger and the work I was doing would be even more valuable to more people.

How did you help NeXT succeed?

KC: Let's build a web browser. Let's build image viewers—whatever we needed to do.

The web browser being OmniWeb, which is still updated today.

KC: That's true. It's the one I still use.

I use it regularly. It's either Safari or OmniWeb. Occasionally if I have to have some kind of Chromium product, it's Brave. But Safari and OmniWeb pretty much keep me going.

Once NeXT folded back into Apple and took on a new life with an injection of energy, how did that change things?

KC: We had just about despaired that NeXT was not going to make it, that we were going to have to give up on this effort to help NeXT succeed. They were turning into a Windows tool vendor with WebObjects for Windows, doing backend stuff, and though we did some WebObjects consulting and helped build some of those early websites, that really wasn't where our passion was as much as building productivity software for the desktop.

We started looking at other options. We started consulting for Sun and helping them maybe build Java into this same sort of thing—they were thinking maybe Java would be the desktop. Then in the last two weeks of 1996, we heard that Apple was buying NeXT. We were thinking, "How can we get out of this Java work we're doing and start going back to Objective-C and AppKit and the environment that we loved?"

When you were building productivity software at the time, what were the actual tools you were selling?

KC: Alongside our web browser, we were still mostly consulting, working on other people's projects, even when they were desktop productivity apps. The big vendor on the NeXT platform at that time was Lighthouse Design. They ended up getting purchased by Sun because Sun wanted to turn Java into this desktop environment.

They were taking their suite of productivity apps—things like Concurrence, which was the tool that Steve Jobs was using to do his presentations back then, like a version 0.1 of Keynote—and a diagramming app called Diagram, which is very much OmniGraffle. Those were the two we mostly helped out on. We also helped on some project management software.

Launching Omni Products

Apple purchased NeXT, and you were still building some of these services. There was a bit of a leap that you eventually made to start launching the Omni products we know today.

KC: We had built OmniWeb back in 1994, and we actually sold it through Lighthouse Design—they marketed it for us. We didn't have any salespeople; we were just programmers who didn't know anything about that world. They printed the boxes and did the marketing. I even wrote the documentation, I think.

Software boxes. Good times.

KC: Yeah. I have them here on my shelf. I am one of those people who collects old software boxes—there's a lot of nostalgia wrapped up in those boxes.

We had OmniWeb, a few tools like OmniDiskSweeper that's still around, image viewing, a CD player—just whatever the platform was missing that we could do to help make things better. The other thing we were doing that was more consumer-focused was helping with game ports.

John Carmack was developing on the NeXT platform, building software cross-platform to run on DOS and Windows. We ended up helping him make Doom run better on NeXTSTEP/OpenStep. Then he contacted us when he needed a 3D driver for this Rendition graphics card prototype, and we started helping with porting Quake over.

As Apple bought NeXT, we started porting Quake to the Mac platform, and then helping other companies with games like No One Lives Forever and a whole bunch of games around that time using the Quake engine and other engines like in Giants: Citizen Kabuto. Some fun times.

You established yourselves as the people bridging the gap between what NeXT had been and what Mac could be, trying to help make sure the Mac was going to go somewhere. There were real concerns in 1997 about whether this platform would survive.

KC: Yeah, in the nineties it felt like it was dying, like Apple was not going to make it almost.

At what point did you realize that this is starting to get traction?

KC: For us, coming from the tiny NeXT platform, even going to the larger Mac platform—when that merger happened at the beginning of 1997, Apple was selling about as many Macintoshes every month as NeXT sold of their operating system during the entire lifetime of NeXT. So it was already operating on a very different scale from our point of view.

There was some success there, but the trajectory was going in the wrong direction. When Steve came in and simplified the product line and said, "Let's build an iMac, let's build a Power Mac, and just have one thing in each of these four quadrants," that drastically simplified things. That was when it started to feel like there was a better direction, and certainly when the iMacs started doing well, helping people get online. Then when Mac OS X finally shipped and the NeXT technology really was now the basis of the new Mac platform—that was when it felt like a great turning point.

What was the point where you started to launch the productivity tools that have really put your flag in the ground?

KC: As Mac OS X went into beta, we had our web browser ready, which was well received because at that time, most web browsers did not have great-looking fonts and typography, and that was something we had in OmniWeb. At the same time we were working on OmniGraffle, building our diagramming software. We had already started working on OmniOutliner as well, so we had all three of those products ready by the time Mac OS X shipped.

It still wasn't enough—not enough of the Mac community was ready to switch over to this completely new operating system for us to fully transition away from consulting right at that moment. But we started the transition at that point. We still wanted to do some more games because we thought that helped the platform, but maybe that wasn't going to be what we wanted to do forever. Let's focus on our own stuff and keep building OmniGraffle and OmniOutliner and make them better.

The Productivity Philosophy

What was it about the productivity space that made you passionate about building in it?

KC: Just like I felt it was useful for me to adopt better tools as a developer—that was what made me adopt the NeXT platform—I felt like if we could do something similar for customers who are trying to get work done using their computers, then that would be a good thing for the world. If everyone can just be more productive, I don't know if it's an idealistic sort of approach to things, but that's just what motivates me.

Are we not idealists though? I think there's value in being idealistic, in having something that you hold up as a higher value. You've talked before about craftsmanship as a value. How do you protect that craft ethos in a software and business world that rewards speed and iteration and hype a lot more than polish?

KC: I guess we just tune out that part of the world for the most part. To some extent you can't, because there's a lot of money going in those directions and we see advertising for a lot of things that can dominate the conversation. But because our motivation isn't directly about money—obviously we need money to succeed, so we can't ignore money in the question altogether, or we wouldn't be able to keep doing what we're doing—but it needs to come secondary from our point of view to building great software in the first place.

If we can build great software and make enough money to keep doing it, and if we can help our customers feel more productive and hopefully have them enjoy using our software—not just be more productive, but have it be software that they enjoy sitting down with and using—then we feel like we're on the right track.

From my perspective, you are definitely on the right track. I still sit down and use the Omni products and feel a sort of lightness that I don't feel with other tools. I use OmniOutliner for most of my writing, OmniGraffle for social graphics and YouTube thumbnails, OmniFocus daily to manage my business, my writing, and being a parent with a 9-year-old. There is still a lightness and a joy to them that I find unmatched by a lot of the newer tools.

KC: Thank you very much. That's really nice to hear, and that's part of what motivates us—hearing things like that.

Native Apps vs Web Apps

A huge number of productivity tools today are essentially web apps in desktop wrappers, whereas Omni by contrast continues to build truly native applications. What advantages do you believe native apps still confer in 2025? Do you think the industry is missing anything by drifting more towards browser-based experiences?

KC: This is an interesting progression that we've seen go back and forth many times over the decades. I think of web apps as being the modern incarnation of mainframe apps, where it's running on somebody else's computer that is hosted by them somewhere—you don't necessarily know where—and you connect to it from your local system with a terminal that's a window into that.

You're dependent on them continuing to keep that system running, and they're hosting all of your data. There are a lot of interesting things about that world. I used to be a Unix systems programmer, and it's fun that you have multiple users actively using the same computer at the same time, so you can do some interesting interactions.

Then you had the PC revolution where people were starting to move more of this power to their own desktops and have a completely independent computer under their own control. The network wasn't fast enough for them to do very interesting things on it yet, so most of what they did was just on their local machine.

I view the current world colored by my eighties perspective—this is really the same sort of thing happening again. But it's different because our computers, our local systems, are now powerful enough to run this stuff. I can run OmniFocus on my watch. And the network is now fast enough that it's much easier to reach the server. There's a lot more parity about what you could accomplish in either place, and you have some choices about it.

To get back to your question: what do the native apps do better? It gives you that control, that independence. You don't have to worry about what happens. How many of the services that you talk to right now can you be certain you will have access to in 10 years? It's really hard to guarantee any of those services you can't access, whereas anything that's running on your local device—if it can run on that device when it's unplugged from the internet, it'll be able to run on that device when it's unplugged from the internet in 10 years. There's nothing you lose control over that way.

Beyond that level of control and privacy—because if the data's in somebody else's computer, they have access to it—there are also just a lot of details you can do when you take advantage of your local processor in a way that's not just providing a terminal to the internet. A terminal to the internet is by design least common denominator, so you're not taking advantage of your local hardware's capabilities nearly the same way as a native app might be able to do. You're not necessarily going to have good Time Machine integration, Spotlight integration—all sorts of things that happen on your local device just don't happen in the cloud.

At the same time, there are lots of things that happen in the cloud that don't happen on your local device. So it's a trade-off for sure.

OmniFocus does have a web version, which is probably the closest anything at Omni Group gets to cross-platform. How are you thinking about those trade-offs when you're building OmniFocus for the web versus for the native device?

KC: Our primary focus is on the native app. That's where the features come first, that's where all the design work happens first. But we build OmniFocus for the web because we know people live in a world where they don't always have control over what device they're using. Maybe they're using a Windows box and they aren't able to run OmniFocus on it, like when they're at work.

To make it as good as it is on the Mac, iPad, iPhone, Apple Vision Pro, and the Watch, we would have to spend more effort than we currently spend. We could become web developers—and we have been in the past—but that's not really where our passion is.

My inclination would be, if we wanted to do something cross-platform, I would still want to take advantage of your local device more than just building something that runs in the browser. We wrote a web browser, so we're pretty familiar with what the limitations are. We would rather write something that's maybe a cross-platform Linux app that you can run on that hardware yourself, because then we don't sacrifice the control over where your data lives and we take advantage of more of your local hardware capabilities. I think that would be philosophically closer to where our heads are at than becoming web developers.

Part of the reason we decided to focus on one platform was because it would take us further if we could put our attention in one place.

The Browser Wars and AI

We are in the middle of what some people are calling a new browser war, with AI browsers like the ChatGPT browser, Perplexity browser, Arc browser. Do you see OmniWeb making a comeback, making a great big splashy return at any point?

KC: I don't know that the answer is yes necessarily. It's an app that I plan to not stop working on, but it's an app that has been relegated to my spare time now for the last 15 years or so. I certainly have been following that with interest and thinking about that space. Since at this point I'm not trying to sell OmniWeb, I'm just trying to use it, a lot of what goes into it is focused on what I need at the moment. That's not to say I wouldn't enjoy hearing from other people about what they need, but sadly I don't have a lot of time to invest in it directly. Maybe that would change.

I really appreciate using OmniWeb because I don't feel like there are chatbots about to be forced into my sidebar. It's not that I'm anti-AI; I just like for things to be in boxes. I like to be able to use my web browser and then if I want to use a chatbot, I can go and open that app.

KC: Yeah, if you think about how we've been integrating the Apple Foundation models into OmniFocus and now into OmniOutliner 6, you can imagine how we might do something for OmniWeb as well, where we would make it part of our plugin system that lets you make those choices as the user of how you want things to integrate. Or if you're a plugin developer, you could build something on top of the app as a platform, but without an agenda where we're trying to push something on people.

The work with the Apple Foundation models has been very cool to play with. I've been using "Plan for Me" and the plugin to estimate how long a task is going to take, and that's been quite useful. There's a nice, mindful approach to AI there. I haven't used the OmniOutliner 6 AI plugins yet, but I'd be keen to hear how you're thinking about which of these tools to build.

KC: Our first step is just to make that capability available to people and not propose a specific solution, although we built some example plugins like "Plan for Me" and "Estimate" just to help people have something they could use right off the bat without having to write their own code. That's not a great experience for people either if they see this thing is there but they don't know how to use it and it's just out of reach.

Hearing what people might be interested in or want to do with something is one way for us to guide what we would work on next. The other day I was playing with how we might integrate into OmniGraffle. In this case, I was using the Qwen3 Coder model running locally on my Mac. I noticed that somebody had done a SwiftUI architecture diagram where they had a little class and said, "Could you diagram this for me?" and they did a little text-based diagram.

I thought, if it can do that kind of text diagram, it ought to be able to do it in OmniGraffle. So I reproduced the same question in my session and said, "In OmniGraffle I can select this, build that same diagram and then use Copy as JavaScript—this is the JavaScript it gives me. Could you change that diagram and spit out the JavaScript that would make this thing?" And it did. Fun to play around with.

It put things in maybe surprising places—there are lots of different ways to think about how you diagram something—but it was interesting to play around with. I don't know whether that necessarily is the right thing that people are going to want, but it was also interesting that I could take a diagram I had built and paste the JavaScript into the chat session and ask it what the diagram is about, and it could actually come up with something interesting.

You've used the word "play" a few times here. You still think about building technology as a form of play, as something to enjoy and to explore without necessarily having a clear end goal.

KC: I sure hope it's play for me. I hope it's play for other people too. I know it's not for everybody, of course, but where it can be that, I love what I do and I want other people to enjoy what they're doing.

AI and Development

Obviously vibe coding has been a thing. How are you thinking about using AI as a developer?

KC: Not as a vibe coder, for sure. I define vibe coding as describing the outcomes you want and not caring about the implementation. I do care about the implementation deeply—it happens to be part of the fun for me. Why would I want to take the fun out of my coding process?

There are some things that large language models can help people save time on—maybe doing some repetitive tasks or translating from one programming language to another. But I really don't trust their work. Every time I play around with it, it saves some time on maybe rote work, but then it adds some time in terms of supervision time. Where that balance is, is a good question, but I'd want to be super careful with what kind of results I was getting out of it.

That's setting aside all the questions around how these things are being trained. When I do use them, I only run local models on my own hardware, so I know where the power's coming from and how much power it's using.

You are not about to turn all of Omni Group onto Cursor tomorrow.

KC: If somebody else has that idea and wants to ask Cursor to build the Omni Group apps, I would be interested in seeing what result they get out of it.

How protective do you feel about the way that Omni Group has built things? OmniFocus has a very specific point of view for how to work and how to get things done. If people started copying those features into cross-platform apps, how would you feel about that?

KC: People have and do. As we were coming over to the Mac platform and we wanted to make sure everything succeeded, we started publishing a bunch of our source code for people so they could learn from it and build things that maybe weren't what we were building but would help the platform as a whole. That's all stuff that moves things forward.

Moving things forward is my goal, and it's not necessarily that people have to be buying our software for it to be moving forward. If other people are taking our ideas and building other great ideas beyond that, then I guess we've succeeded in a sense—we got to move things a step forward and somebody else picked up the ball and moved it further again. Every time I see an OmniWeb feature in another browser, that's how I try to feel about it.

Vertical tabs.

KC: Yeah. Every time I see a new app come out and they announce vertical tabs, I'm like, "I remember vertical tabs. That's what I use in my current browser, OmniWeb."

It's a little disappointing to me if they never give credit, if people never acknowledge where things came from, but it's more important for me to just see things keep moving forward. I do live in this world where I want things to be moving forward, not backward.

Personal Productivity

I'd love to hear about how you personally organize your work, how you use OmniFocus and OmniOutliner and how you approach your day at Omni Group using the tools that you have.

KC: I have both apps running all the time. I have a lot more OmniOutliner windows open at any one time than OmniFocus windows. OmniFocus might often be hidden, in fact, because a lot of the tasks I do for work, we track in our bug tracking system, which is something we built back when we registered omnigroup.com—in 1991, the OmniBugZapper.

That's where my work lives—tracking what's going into the next version of OmniOutliner, for example. Here's a list of things with milestones associated with them, priorities, who's assigned to it, what the current status is, all that kind of stuff. So none of that work is in OmniFocus.

OmniFocus helps keep track of the stuff that is not being tracked by OmniBugZapper. Sometimes it's to capture things that aren't yet in BugZapper that need to get there eventually. I have things tagged for OmniBugZapper, and sometimes I'll just say, "Oh, remind me to do this," and later I'll see that thing in my OmniFocus database and I'll go file a real bug for it that other people can see.

Through the day, I'm not living in OmniFocus as a place to act on plans so much during my workday. It's a place where I'll capture things for doing stuff later so I can basically move on with my life and not be distracted by something or worrying that there's something I forgot that I need to get done.

Whereas OmniOutliner is a place where every time I'm working on something—if I'm working on a blog post, I might outline it in OmniOutliner. If I'm taking notes in a meeting, I'll take those notes in OmniOutliner. When I used to do meetings in person, I would usually write with pen and paper, and then later I would go back and write up those notes in OmniOutliner. The process of outlining the notes I had just taken was often a way to help clarify the ideas for me and made it more useful, even if I never looked at that outline again. The chance to do the rewrite really helped me process it and make it more useful to me.

I have a lot of outlines around things like "What are the product features we're trying to emphasize for this next version of an app or for this release?" I use both apps a lot.

What non-Omni tools do you use? Are there any non-Omni tools that you love?

KC: Of course. I use Apple's built-in tools—Mail, Messages. For work we use Mattermost. We use Discourse for forums for communicating with customers in a long-term way where you actually have history that lasts. We also chat with customers on Slack. You'll notice there are a bunch of these web tools that are the non-Omni tools and non-Apple tools.

Some of the native third-party tools I'll use are little things like SF Symbols for thinking about which symbol I'm going to use when I'm designing something. There are a lot of little things like that, but I spend a lot of my time either in Omni tools or in Xcode or in Terminal. Terminal's a big part of my life for sure. A lot of open terminal windows.

OmniOutliner 6

Before we wrap up, OmniOutliner 6 went out for testing yesterday. I started using it and I'm already falling in love with it. I would love to hear some thoughts about how you got to OmniOutliner 6 and what questions you were trying to solve.

KC: The first thing on our minds as we were designing OmniOutliner 6 is that we wanted it to be a universal app. When I say universal, obviously I'm talking about Apple platforms. It had started out as a Mac app at the start of Mac OS X. We had brought it to the iPad when the iPad came out with our "iPad or Bust" initiative back in 2010. Then we were in this world where we were going back and forth—now we'll do a Mac release, now an iPad release. We wanted to get away from that back-and-forth development process and instead do a unified development process, much like we've already done for OmniPlan and OmniFocus, where we release a new version for all the platforms at the same time.

Which has its own challenges, but it's easier now than it was 15 years ago because instead of having completely different UI frameworks—AppKit or UIKit—we now have SwiftUI where we can write shared code that runs on both at the same time. Not all of our code has been moved to SwiftUI, but there's a lot of common code now that can be shared. We wanted the feature set to a place where it had a lot more parity across all the platforms, where you buy the app once and you use it across all your devices. That's just how we think people work these days.

If you have all of your data across all the devices, what does that mean for not just the capabilities of the app but how you treat your data, how you have data linked to itself? We realized we had a problem there to solve, and that's where OmniLinks came into the picture.

Early versions of OmniOutliner already had support for links to other documents, so that isn't itself a new feature, but those links were based off file aliases and other Mac-specific technology that never made the transition over to iOS, which was originally a file-less system. All of that technology had to be rethought about how you make this portable from one system to another.

Back when we wrote the linking for the Mac, there really wasn't as much expectation that you'd be using multiple systems throughout the day. It was already a little bit broken if you went to share a document with somebody else and their username was different, so the paths were different. As the world started syncing and using completely different platforms, all that ability to reference content from another outline got lost. We wanted to get that back into place. That's really the problem we set out to solve with OmniLinks, and that's a big part of the OmniOutliner 6 push.

Another big interesting thing that happened was just this last summer, Apple introduced Liquid Glass, which is the first time they've done a design system across all of their platforms at once. Having a design system that's designed to be consistent—even if it's not perfect—is a big improvement. Having buttons that actually look like buttons on every platform, having the consistency so that now it's easier for us to document or take screenshots and have it look the same across platforms—there's a lot of value there. We wanted to take advantage of Liquid Glass. That's also an important part of doing a universal app now that works across everywhere.

We also set out specifically to add features that were missing on iPad. Full control over styles—when we originally did the iPad app, we were trying to make sure all the semantic content came over, but UIKit didn't even support rich text very well yet at that time. We had to build our own RTF reader. We didn't even try to match the appearance of the documents very much back then, but it became clear over time that what we actually wanted was to have full control parity. The ability now to inspect styles and see what's contributing, have full hierarchical styles and named styles and all of that—exactly the same on the iPad—with controls like vertical line or indent controls. That was another big piece of what we were working on.

Multi-window support on the Mac was another big feature we wanted. When I say multi-window support, we've always had multiple windows where each window was its own document, but we wanted the ability to open multiple windows on the same document. Maybe you're working on a really long outline—when I helped my mother with her doctoral dissertation, she was working in Word at the time, and we pulled it into OmniOutliner so we could restructure things in a much easier way than trying to move paragraphs around in Word. Once we got it the way we wanted, we exported it back out to Word and she went on and published her dissertation.

In that process, we were working with a very long outline, and it would have been great to be able to see the top at the same time as you're looking at the bottom, or have one view where all the elements are collapsed and the others are open. That's another big feature that we now have on the Mac.

To come back to OmniLinks—another problem we wanted to solve is that a lot of people at Omni use outlines a lot through their days, and we share these outlines. We want to be able to send somebody a link to an outline instead of saying, "If you go look in my staff folder and get into the documents, you'll find the latest plans from this meeting or whatever." Instead, I could just send you a link and have it be something that is shared and that they can open as easily as a link.

That's one of the things I think has been driving people away from native apps recently to cloud-based apps—this ability to universally link to content and share it and reference it that way. That was another problem we set out to solve with OmniLinks, and I hope what we have done.

I've already started using OmniLinks to much more cleanly manage the documents that apply to tasks. It's been great—I'm only a day into using it, but it has been great.

KC: Yeah, and it's nice that you can share those links anywhere. You can link to them from your wiki page or guide. We call it Guidebook internally, but you could put a link into OmniFocus and then just pull up that reference content.

It's been very smooth. So congrats on that. Here's the hot question: Are we going to see a Liquid Glass OmniWeb?

KC: Oh yes, for sure. What exactly that all looks like—well, you can imagine what some of that would look like.

I'm keen to see it. That is everything I had on my list of questions, except for one thing which I always ask everyone: Is there a question that you wish somebody would ask you?

KC: Oh goodness. I have not thought of that question. Thank you for asking that question. There probably is, but I probably don't know what it is.

A fair enough answer. This has been fantastic, Ken. Thank you for sitting down and chatting with me. Congrats again on OmniOutliner 6, and it's just been great to connect.

KC: Thank you so much for your time and for reaching out. It's been great to have this conversation with you.

The magpie is nature's most indiscriminate collector.

Show it something shiny and the bird will grab it, haul it back to its nest, and arrange it among the bottle caps, aluminum foil scraps, and occasional piece of actual jewelry it has assembled into a chaotic masterpiece. The magpie doesn't follow a system. It doesn't read books about optimal nest-building techniques or watch YouTube videos about the Marie Kondo method for corvids.

It sees something that works, takes it, and uses it.

And somehow, at the end of all this apparently haphazard gathering, there's a nest...

People ask me about my productivity system. They want to know if I use Getting Things Done, or Bullet Journaling, or Zettelkasten, or some other methodology with devoted adherents and PDF instruction manuals.

The honest answer is that I use all of them and none of them.

I'm a magpie.

We are in what might be called the golden age of productivity discourse. There are more systems, frameworks, and philosophies for organizing your life than ever before in human history. David Allen wants you to capture everything in an external system and process it through specific channels. Tiago Forte wants you to build a Second Brain using progressive summarization. Ryder Carroll wants you to rapid-log in a physical notebook using a specific notation system. Each approach comes with its own vocabulary, its own tools, and its own community of practitioners who will happily spend hours explaining why their chosen method changed their life.

Every single one of these systems works for someone. Getting Things Done genuinely transforms lives for people whose brains work a certain way. Bullet Journaling provides structure that some people desperately need. The problem comes when we treat these systems as complete, hermetically sealed units that you either adopt wholesale or reject entirely.

The magpie knows better. It understands something that productivity gurus spend entire books dancing around: good ideas are where you find them. The optimal approach isn't to pledge allegiance to one system and defend it against all competitors. The optimal approach is to steal liberally from everything and build something that actually functions for your specific brain.

I use Getting Things Done's weekly review concept, but I do it in Apple Notes or on Index cards or post-it notes, or a Field Notes book etc instead of any dedicated home. What matters isn’t the record, so much as the activity itself.I've borrowed Bullet Journaling's practice of migrating tasks, but I do it digitally rather than in a physical notebook. My note-taking system uses elements of Zettelkasten's linking approach, mixed with some ideas from progressive summarization, implemented in Apple Notes and occasionally Obsidian and occasionally iA Writer, because any one of them could // might be the tool that felt right in that moment. For writing projects, I keep a a few things listed in a Numbers spreadsheet, and a few in an Apple Note, and a few in OmniOutliner. I have tasks that float between Reminders and OmniFocus and some scratched out lists.

Does this sound coherent?

No. No it bloody well doesn’t.

It shouldn't, really.

There's no unifying theory here, and I do not have an elegant framework that explains why these particular elements work together. But it does work. It works for me. It works better than when I tried to faithfully implement GTD in its pure form, or when I spent three months attempting to maintain a perfect Bullet Journal. Those attempts failed because I was trying to adopt someone else's complete system, built for someone else's brain, solving someone else's problems.

When you read about a productivity system, you encounter dozens of ideas, some brilliant, some situational, some actively counterproductive for your circumstances. The GTD book contains genuinely transformative insights about externalizing commitments and defining next actions. It also contains a lot of guidance about filing systems and reference materials that may or may not make sense to // for you. Should you reject the entire methodology because some parts don't fit your life? That seems wasteful.

The magpie approach = a truth that system-builders often obscure: productivity advice is contextual. What works depends on your job, your cognitive style, your life circumstances, and even your current season of life. And seasons...well, they change, don’t they?

A system that's perfect for a freelance writer might be completely wrong for a software engineer. Strategies that work when you're single might collapse when you have a kid. And then again, when you have a second.

The rigid adoption of any single methodology ignores this.

We all want the security of following a proven system, the confidence that comes from doing things "the right way." I understand that impulse. There's comfort in both structure and in knowing that thousands of people have followed this path before and found success. But systems become crutches when we let them override our own judgment about what actually helps versus what's just system maintenance for its own sake.

The internet has made us all cargo cultists to some degree. We see someone successful describe their process and we assume that their success flows from that process. We copy the external forms without understanding which elements actually matter. Maybe the successful person's elaborate morning routine contributed to their achievements, or maybe they succeeded despite it, or maybe the correlation exists only in their mind as they constructed a retrospective narrative.

How would we know?

What helps (me, at least) is radical pragmatism. Take the idea, try it for a few weeks, and observe whether your life actually improves. If weekly reviews make you feel more in control, keep doing them. If they feel like an empty ritual, stop. If physical notebooks help you think, use them. If they just create clutter and you never look at them again, switch to digital. The goal is to build a nest that works for you, not to achieve the ideal of productivity system purity.

This goes beyond productivity tools. Why do we feel compelled to choose one parenting philosophy, one diet approach, one exercise methodology? The magpie knows that you can respect attachment parenting while occasionally using techniques from other approaches. You can mostly eat whole foods while maintaining some processed convenience items that make your life workable. You can lift weights and do yoga without pledging allegiance to either camp.

The nest you build from stolen shiny objects might look chaotic to outside observers. It isn’t suited for lifestyle blogs or productivity podcasts. But if it holds your eggs and keeps you functional, who cares whether it follows someone else's blueprint?

The magpie builds what works, takes what helps, and moves on from what doesn't.

Maybe we should try doing the same.

I’ve been writing 1000 words every day for about 10 years now, and I’m still not always sure what I’m doing. Arguably, most of that output is terrible. Some days I manage maybe two hundred words before I run out of things to say and end up describing what I had for breakfast.

But those three years have changed how my brain works more than any other single habit, routine or belief in my life.

When people talk about daily writing, they mean it as career advice for aspiring novelists or bloggers. You’ll get better at the craft, build a portfolio, develop your voice etc etc. All true, probably.

I think we’re missing something bigger:

Writing every day is less about becoming someone who writes, and more about becoming someone who thinks.

Thoughts are slippery. You can hold an opinion about something, carry it around for years, defend it in conversations, and never actually examine whether it makes any sense. I used to have all sorts of views about politics, relationships, productivity, etc. 

Then I started trying to write them down, and about half of them evaporated the moment I put them into sentences…

In conversation, if someone pokes a hole in your logic, you can say “well, you know what I mean” and move on. You can gesture vaguely at the general direction of your point. When you write, you can’t handwave. You can’t bluster and obfuscate your own ideas into oblivion. When you’re alone with a blank page, there’s nobody to rescue you with a charitable interpretation.

Your argument either holds together or it doesn’t.

Writing is thinking with the training wheels off.

I’m not claiming you need to write a daily philosophical treatise. My daily writing is usually mundane. I’ll work through why I’m annoyed about something in my work or home life, or try to figure out whether I actually need to move to a new note taking app or just want to want to move note taking apps for the sake of it. The topic matters less than the act of forcing vague feelings into specific words. Once something is written down, you can look at it up close. You can ask whether it’s actually true.

There’s a concept in programming called rubber duck debugging. When you’re stuck on a problem, you explain your code line by line to a rubber duck. The act of articulating the problem out loud helps you spot the bug. Daily writing is rubber duck debugging for your entire life. You explain yourself to the page, and suddenly the contradictions become visible.

I think part of why this works is that writing creates distance. When a thought is in your head, you’re too close to it. You’re inside it, experiencing it, identifying with it. But when you write it down, it becomes an object you can examine. Anxiety, written out, stops being a shapeless dread. And once you can see what it actually is, you can usually do something about it.

The act of processing experiences through writing seems to cement them. I remember conversations I wrote about years ago with startling clarity, while entire weeks where I didn’t write have blurred into nothing. Maybe writing creates hooks in memory. Maybe it just forces you to pay attention in an increasingly skewed attention economy.

Fair enough.

Everyone’s got limited hours and too many demands on them. 

But I think we’re probably talking about fifteen to twenty minutes here. 

Maybe thirty on a good day.

You’re not writing War and Peace. You’re writing enough to clarify one thought, work through one problem, capture one observation. That’s perhaps the length of three or four text messages to a friend, composed without chatGPT.

You don’t need interesting material. You’re not performing for an audience. You can write about why you chose the lunch you chose, or what you noticed on the walk to the store, or a single, unmarked moment in a conversation that stuck with you. The point isn’t to produce great content. The point is to practice putting thoughts into words.

I used to think clarity of thought was an innate trait some people had and others didn’t — that some people were just naturally logical and articulate. Everyone else was stuck thinking in circles and trailing off mid-sentence.

But I don’t believe that anymore.

I genuinely think clarity is a skill, and like most skills, you get better at it by practicing.

Writing  - every day -  is practicing thinking clearly over and over until it becomes almost natural.

If it feels like your thoughts are muddied, or you have trouble making decisions, or you keep having the same arguments with yourself on repeat, try writing for fifteen minutes a day. Try it for a month. Don’t do it with publication in mind, don’t do it for posterity, don’t do it for the likes, don’t even write for your future self. Just write for the sake of it. Write to see what your own thoughts look like when you force them into sentences.

You might be surprised by what’s actually in there.

The practical upshot is probably this: if your bottleneck is clarity of thought rather than execution, daily writing is worth trying. And if you try it for a month and it doesn’t help, well, that tells you something too — maybe your thinking is already pretty clear, or maybe your problems are in a different domain entirely.

Worst case: you’ve lost twenty minutes a day that you’d likely have lost scrolling your phone anyway.

Best case, you’ve debugged your own cognition.

There is a particular trap that catches people like us.

And I say "us" because if you're reading this, you probably know exactly what I mean.

You're the person who needs to understand the underlying mechanisms before you can act. Who reads three books on negotiation tactics before asking for a raise. Who spends weeks researching the optimal workout routine instead of just going to the gym.

We are the people who - far too often - mistake intellectual clarity for progress.

In Zen and the Art of Motorcycle Maintenance, Pirsig talks about the South Indian Monkey Trap. You drill a hole in a coconut, put rice inside, and wait. The monkey reaches in, grabs the rice, but then can't pull its fist back out through the hole. The monkey could escape by letting go of the rice, but it won't. It'll sit there, trapped by its own grip, while the hunters approach.

I think about that monkey a lot. Particularly when I catch myself reading a fourth article on habit formation instead of just flossing my teeth...

The problem: all this analysis feels productive.

Your brain gives you the same little dopamine hits for understanding something as it does for doing something. Maybe even bigger hits, honestly. Understanding is clean and controllable and it happens entirely in your head (where you're safe.) Action is messy. Action = other people and uncontrollable variables and the possibility of looking stupid.

Of course your brain would rather stay in theory mode.

I'm not going to sit here and tell you to stop thinking and just do things, man. That advice usually comes from people who've never experienced analysis paralysis, and it's about as helpful as telling a depressed person to cheer up. I’ve been that // there, too. It doesn’t help.

Our analytical approach has real value. Understanding systems and mechanisms and underlying principles actually does help us act more effectively when we eventually act. The trouble starts when the understanding becomes a substitute for the action rather than preparation for it.

There are aspiring writers who've read everything about story structure but haven't written a complete story. Entrepreneurs who can discourse brilliantly on business models but haven't made their first sale. People with encyclopedic knowledge of social dynamics who still can't make small talk at parties.

The model gets more and more refined while the territory remains unexplored.

I think the issue is that we treat these two things as if they exist on the same spectrum. Like you do some analysis, then some action, then more analysis, then more action, and you can slide back and forth between them smoothly. But they're actually different modes of being. Analysis happens in the realm of abstraction and infinite possibility. Action happens in the realm of the concrete and the constrained. You can't smoothly interpolate between them.

There's a gap you have to jump.

And jumping is scary.

Once you act, you've collapsed the wave function. You're no longer dealing with the perfect platonic ideal of what you could do; you’re stuck with the messy reality of what you actually did. Your beautiful model meets the territory and turns out to be wrong in eleven different ways you didn't anticipate. This is uncomfortable for people who pride themselves on being right.

Perhaps (perhaps) we don't fear action so much as we fear feedback. As long as our model stays in our head, it can be perfect. The moment we test it against reality, we have to confront our wrongness. And for highly analytical people, being wrong feels like a moral failing rather than a normal part of learning.

I've noticed a few things that seem to help:

First, you have to get comfortable with the idea that your model will always be incomplete and partially wrong. Always. You could spend your entire life refining your understanding of how to write a novel, and you'd still learn more from writing one bad novel than from all that study. The territory is infinitely richer than any map can capture. This isn't a bug, it's a feature. If the map could be as detailed as the territory, it would be the territory, and thus useless as a map.

Second, you need to deliberately practice the jump between analysis and action, by setting very clear boundaries on it. I'll research workout routines for two hours, then I'm going to the gym regardless of whether I feel ready. I'll think about what I want to say in this email for ten minutes, then I'm sending it whether or not it's perfect. The analytical part gets its time, but then you act anyway. You're training yourself to be okay with the gap.

Third, and this is harder, you have to learn to metabolize feedback differently. When reality contradicts your model, it’s not a failure signal; it’s data. Neutral, immutable data. That's the whole point of making models in the first place, to test them against the world and update them. But you can only get that data by acting. The model serves the movement, not the other way around.

I still build systems. I still love understanding how things work. I still spend probably too much time reading about things instead of doing them. But I'm trying to hold it all more loosely now. The map is useful precisely because it's not the territory. And I'm learning that sometimes you need to crumple up your beautiful map and just start walking.

You'll probably go in the wrong direction at first. You'll definitely look silly. Your model will turn out to be wrong in ways you should have anticipated and ways you couldn't have. But at least you'll be moving. At least you'll be generating the level // category of knowledge that only comes from contact with the real world.

The monkey can let go of the rice any time it wants.

Thirteen point eight billion years ago, there was nothing, and then there was everything.

The universe exploded into existence in a roiling chaos of energy that gradually cooled into quarks, then protons, then hydrogen atoms. For about 380,000 years, the cosmos was an opaque fog of matter and radiation so dense that light couldn't travel through it. Then the fog cleared, and the universe became transparent.

For millions of years after that, there were no stars. Just hydrogen and helium drifting in the dark, pulled together by gravity into increasingly dense clouds. Eventually, around 100 million years after the fact, those clouds collapsed enough to ignite the first fusion reactions. Stars lit up across the universe like someone had turned on a vast chandelier. They burned, fused heavier elements in their cores, exploded as supernovae, and seeded the cosmos with carbon, oxygen, iron, everything that would later become planets and people.

About 4.5 billion years ago, in an meaningless corner of an unremarkable galaxy, a cloud of gas and dust collapsed to form our sun and its retinue of planets. Earth coalesced from the debris, a molten ball that slowly cooled and developed a crust. Asteroids and comets bombarded the surface. Somehow, in ways we still don't fully understand, chemistry became biology. Single-celled organisms emerged around 3.5 billion years ago, and for the next three billion years, they had the planet to themselves.

Then came the Cambrian explosion, and suddenly (in geological terms) there were trilobites and strange worms and the ancestors of everything that would follow. Fish developed jaws, some crawled onto land, dinosaurs ruled for 165 million years and then abruptly vanished. Mammals diversified in the aftermath, primates emerged, and around 300,000 years ago, in Africa, anatomically modern humans appeared.

For most of human history, we lived in small bands, hunting and gathering. We figured out fire, language, tools, art. Around 10,000 years ago, we started farming, and everything accelerated. Civilizations rose and fell, writing was invented, empires sprawled across continents. The Bronze Age collapsed, the Iron Age began, religions spread, the printing press changed everything, the scientific revolution transformed our understanding of reality, the industrial revolution transformed how we lived, and through it all, millions upon millions of the critters who now identify as human were born and died and were entirely forgotten.

And then, at some point in the late 20th or early 21st century, you were born. Your parents met through some improbable chain of circumstances. Your father's particular sperm cell, out of millions, happened to fertilize your mother's particular egg. If anything had gone slightly differently, someone else would exist instead of you, or nobody at all.

You spent your childhood learning to navigate the world. You went to school, made friends, had your heart broken a few times. You chose a career, or had one choose you. You experienced joy and boredom and anxiety and wonder. You tried to make sense of things. You worried about whether you were doing enough, being enough, mattering enough.

And now you're here.

You're here, and you're probably not going to be a billionaire.

You may (or may not) start a company that changes the world or write a novel that gets taught in schools for generations or discover a new law of physics.

You're probably not going to be a rock star or a movie star or any kind of star at all.

Your Wikipedia page may never exist.

The history books will not mention you.

You will never give a TED talk that goes viral, never have a biopic made about your life, never have buildings or scholarships or awards named after you. When you were a kid, maybe you thought you'd be exceptional, that you'd be one of the rare ones who breaks through, who matters on a grand scale. And then you grew up and realized you're smart enough to understand probability, which means you're smart enough to understand that you're almost certainly going to be ordinary.

You look at your life and you see the ceiling approaching. You see roughly how far you can rise in your career, roughly how much money you'll make, roughly what your legacy will be (small, or more likely, nonexistent). You scroll through social media and see people your age founding companies and publishing books and winning awards and collecting impressive titles, and you feel that familiar tightness in your chest.

The sense that you're falling behind, that you've missed your window, that you're wasting the one life you get. You're here, right now, in this present moment, and you're worried that being here isn't enough. That simply existing and working and loving people and having hobbies and being generally decent isn't enough, that you need to be extraordinary to justify the improbable fact of your existence.

You're here, and you're anxious about it.

I've been thinking a lot about this lately: the sheer statistical improbability of your existence should be crushing, but somehow it's the opposite. You are the product of an almost inconceivable number of contingencies, a soap bubble floating on an ocean of chance. And yet you lie awake at night worrying about whether you're successful enough, whether you've made the right career choices, whether people respect you, whether you'll be remembered.

And by you, I mean you.

And by you, I also mean me.

I used to find this overwhelming. The universe is so vast and old, and I am so small and brief. There are more stars in the observable universe than grains of sand on all of Earth's beaches, and most of them have planets, and the whole thing has been running for billions of years before I showed up and will continue for billions or trillions after I'm gone.

So, what's the point?

Of anything?

But lately I've been coming around to a different view.

The insignificance isn't the problem. It's the solution.

Think about the pressure we put on ourselves to matter, to make a mark, to be significant. We choose careers based partly on how impressive they sound at dinner parties or on imagine appearances on imagined talk shows. We agonize over decisions as if the fate of the world hangs on them. We compare ourselves to the most successful people in history and feel inadequate. The burden of significance is exhausting.

What if you just... didn't matter that much?

What if your choices and achievements and failures were basically rounding errors in the grand scheme of things?

Would that be so bad?

I spend a lot of time writing, and I have this recurring anxiety about whether anyone will read what I write, whether it will have any impact, whether I'll be forgotten immediately or maybe remembered for a while. But when I really sit with the cosmological perspective, when I imagine the trillions of years stretching out ahead after I’ve kicked the bucket // bought the farm // gone for a Burton, the whole question starts to seem sort of quaint.

Of course I'll be forgotten.

Everyone will be forgotten.

The sun will expand into a red giant and engulf the Earth, and every trace of human civilization will be vaporized. All the books and buildings and great works of art, gone. Every reputation carefully cultivated, every legacy anxiously protected will be erased.

At some point, even MC Hammer will be forgotten.

And you know what? That's okay. Better than okay. It's actually kind of freeing.

If nothing you do has permanent cosmic significance, then you can stop trying to achieve permanent cosmic significance. You can do things because they're interesting or fun or helpful to people right now, without needing them to echo through eternity. You can take risks, try things that might fail, pursue projects that won't make you famous or rich or immortal.

The stakes are lower than you think.

I see people paralyzed by the fear of making the wrong choice, as if there's an ageless scorekeeper tallying up their decisions. Should I take this job or that job? Should I move to this city or stay in that one? Should I date this person or wait for someone better? They treat these choices as if they're carving their decisions into a permanent record that will be judged by future generations.

But future generations won't care.

Our generation barely gives a shit about the Great War, about the Model T Ford, or about the life and times of billions of lifeforms who are long gone. We don’t remember the 30 Years War. The vast majority of the human race doesn’t commemorate Culloden.

Future generations will have their own concerns, and then they'll die too, and eventually there won't be any future generations at all. The sun will burn out, the stars will wink out one by one, and the universe will grow cold and dark.

This sounds depressing when I write it out like that, but I promise I'm going somewhere with this.

The liberation of insignificance: it lets you focus on what actually matters to you, right now, without the weight of cosmic importance crushing you. You can be kind to people because kindness feels good, without trying to tip the scales of history. You can create art because creation is satisfying, without competing for immortality. You can love people fully, knowing that love will end (one way or another)and that's fine.

There's something deeply wrong with how we've constructed meaning in the modern world. We've lost most of the traditional sources of significance (religion, community, duty) but kept the anxious feeling that we need to justify our existence. So we've turned to careers and achievements and metrics and status, trying to prove our worth to the horizon. We're all performing significance, trying to matter, desperate not to be forgotten.

But what if being forgotten is the natural state of things? What if almost everyone who has ever lived is already forgotten, and that's just how it works? There are about 100 billion humans who have lived and died, and you can probably name a few hundred of them. The rest have vanished into history, and the world keeps turning.

Call me a sociopath, but I find this comforting. The pressure is off. I don't have to be one of the 0.001% of humans who gets remembered. I can just be one of the 99.999% who lives, does their best, tries to be decent to the people around them, and then peacefully vanishes into oblivion. There's no shame in that. It's what happens to almost everyone, including literally every single one of the people you consider either successful or immortal.

Things still matter, life still matters - just locally and temporarily instead of cosmically and eternally. The meal you cook tonight matters to the people who eat it. The conversation you have with a friend matters to both of you, in that moment. The work you do matters to your colleagues and clients and the people affected by it. But in five hundred years, none of it will matter at all, and that's absolutely fine.

I think we'd be happier if we could internalize this. Not in a nihilistic way, where nothing matters so why bother, but in a liberating way, where things matter in proportion to their actual impact on actual people, not in proportion to how much astral significance we imagine them having. You can care deeply about your life and work and relationships without needing them to echo through eternity.

Once you stop trying so hard to be significant, you often end up doing better work anyway. You're not paralyzed by the fear of failure or the need to prove yourself. You can experiment, play, explore. You can do things for their own sake rather than for external validation. The people who actually do end up making lasting contributions are often the ones who were just deeply engaged with something they found fascinating, not the folks trying to cement their legacy.

But even that shouldn't matter to you.

Whether your work lasts or vanishes, whether you're remembered or forgotten, none of it changes the basic fact of your existence: you are here now, alive and conscious, able to experience the world and other people and double cheeseburgers and your own mind.

That's enough.

That's more than enough.

It's miraculous, actually, that you exist at all.

So here's happens next; here’s what’s coming.

Eventually, inevitably, no matter how much money you raise, no matter if your tweets go viral or you change careers, or we get AGI, or you eat chicken fingers for lunch, or you bio-hack another handful of years together via plasma transplants and longevity podcasts, you’ll die (bad luck).

At first, people remember you. Your family talks about you at gatherings. Your friends tell stories. Maybe there are photos on social media, posts that get surfaced in "memories" features for a while. But gradually, people move on. They have to. They have their own lives to live.

A generation passes, and you're a story told by people who knew you, if that. Another generation, and you're a name on a family tree. A few more generations and you're gone completely. Your great-great-great-grandchildren won't know your name unless you were unusually famous // infamous or kept unusually detailed records, and even then, well…

Humans are forgetful.

The world keeps changing. New technologies emerge, old ones become obsolete. Political systems rise and fall. Mick Jagger eventually succumbs (more bad luck). The climate shifts, coastlines change, cities are built and abandoned. Humanity continues, facing new challenges, solving old problems, creating new ones. Thousands of years pass. Civilizations you can't imagine come and go. Wars are fought, peace accords signed, treaties broken. The pace of change accelerates or slows, nobody knows.

Eventually, if we don't destroy ourselves first, humans might spread beyond Earth. We might colonize Mars, build habitats in the asteroid belt, send generation ships to other star systems. Or maybe we stay on Earth and figure out some kind of sustainable equilibrium. Or maybe something entirely different happens, something we can't currently imagine.

Millions of years from now, if anything descended from humanity still exists, it probably won't remember you. It might not even remember that individual humans once existed. The whole sweep of recorded history might be compressed into a single footnote in some vast database nobody bothers to access.

The sun continues burning through its hydrogen, gradually heating up. In about a billion years, Earth becomes uninhabitable as the oceans boil away. In five billion years, the sun expands into a red giant and likely engulfs the inner planets entirely. Everything humanity ever built, every trace of your existence, vaporized.

But even that isn't the end. Other stars continue burning, new ones form from gas clouds, galaxies merge and separate. The universe expands, accelerating outward, carrying galaxies away from each other faster than light can travel between them. Star formation slows as hydrogen runs out. One by one, the stars burn out. Red dwarfs last the longest, but even they eventually exhaust their fuel.

In perhaps 100 trillion years, the last star flickers out. The universe is dark now, filled with black holes and dead stellar remnants. The black holes gradually evaporate through Hawking radiation over the course of googol years, unimaginable spans of time. Eventually, even protons decay (probably), and the universe consists of nothing but a thin soup of elementary particles and radiation, spreading ever farther apart.

Heat death. Maximum entropy. No more structure, no more complexity, no more life or thought or experience. Just an endless dark expanse, everything that ever happened forgotten completely, with no one left to remember.

And somehow, knowing all this, I feel okay. The heat death of the universe doesn't diminish my lunch today (Salmon Sashimi) or the book I'm reading (In Cold Blood by Truman Capote and the Dragonlance Chronicles by Margaret Weiss and Tracey Hickman) or the conversation I had yesterday that made me laugh. Those things happened, they were real, and they mattered in the only way things can matter: they were experienced by conscious beings who cared about them.

You are insignificant.

So am I.

So is everyone.

And that's a good thing, because it means we can stop trying so hard to be significant and just focus on being alive, right now, in this improbable moment we've been given.

The universe doesn't care about us, and that's okay.

We can care about each other instead.

I spend a decent amount of time at bookstores, and I’ve noticed something.

The adults browsing the fiction section fall into two distinct camps: college students reaching for Penguin paperbacks, and seventy-year-old professors emeriti in tweed jackets. Meanwhile, the self-help aisle is packed with everyone else, thirty-somethings in business casual leafing through "Atomic Habits" and "The 7 Habits of Highly Effective People."

The distribution is bimodal, and I think I know why.

The young read fiction because they haven't yet learned to be embarrassed by imagination. The genuinely brilliant read fiction because they've looped back around to understanding that pure information transfer is the least interesting thing a book can do. But there's a vast middle ground of people who have just enough education to feel insecure about it, and these folks read non-fiction exclusively. They read because they love being seen learning, more than they love the process of it. I know. I’ve been one of ‘em, at various points in my life.

The dirty secret about non-fiction is that most of it could be a blog post.

These books follow a template: introduce a counterintuitive finding, tell three anecdotes that illustrate it, mention some studies (p < 0.05, naturally), provide a framework with a memorable acronym, conclude with actionable advice. Stretch this to 250 pages, add some graphs, and you have a bestseller. The information density is incredibly low. There are zero complex systems of thought to impart; you're learning to repeat interesting-sounding facts.

Fiction (by contrast) smuggles actual complexity into your brain. When Dostoevsky spends fifty pages letting Raskolnikov justify murder to himself, you're living inside a mind that's trying to reason its way to atrocity. You understand something about human rationalization that no Gladwell volume could teach you. The knowledge comes embedded in context, emotion, and contradiction.

It can't be reduced.

I suspect this is why the smartest people I know tend to quote novels more than they quote non-fiction. They'll reference the Grand Inquisitor or mention something about whales etc, and these literary touchstones carry more meaning than any TED talk summary ever could. The metaphors are load-bearing. They contain compressed wisdom that unfolds differently each time you examine it.

What Tolkien accomplished in "The Lord of the Rings" eclipses any and every non-fiction book ever published about leadership or virtue or the nature of power. Middle-earth presents a complete moral universe where power corrupts absolutely, where the small and humble accomplish what the mighty cannot, where mercy and pity have unexpected consequences. You absorb these lessons through narrative, through watching characters make choices and face their results. The Ring is a better illustration of the corrosive nature of power than anything in The 42 Laws - because it's a metaphor, and metaphors work on you in ways that direct statements can’t // won’t // don’t.

There's a reason every major religion transmits its deepest truths through parables rather than propositions. The various authors of the Bible could have written "Seven Habits of Highly Effective Disciples" but instead, they told stories about seeds and soil, about lost coins and prodigal sons. The Buddha could have published "Mindfulness for Beginners" but instead there are koans and sutras full of contradictory wisdom.

Pure information transfer fails to change people.

Stories work.

The “midwit” trap is thinking that explicit instruction is superior to implicit understanding. Someone reads "How to Win Friends and Influence People" and learns techniques. Someone reads "The Unbearable Lightness of Being" and learns what it feels like to be every person in every kind of relationship, to watch love curdle into resentment, to see how societies constrain and shape individual choices.

Which knowledge is more useful?

Which makes you wise?

I used to think I was being practical by reading mostly non-fiction. I was learning things! Accumulating facts! Becoming informed about psychology, economics, history, science. But the conversations that lingered were with people who read novels. They have a different kind of intelligence, more contextual and subtle. They understand human nature in a way that knowing cold facts about cognitive biases never quite captures.

Self-help books operate under the assumption that wisdom can be systematized and imparted through instruction. But wisdom resists systematization. It's pattern recognition across too many variables to count. It's knowing when rules apply and when they don't. Fiction trains this capacity by forcing you to navigate moral and social complexity without clear answers. There's no "key takeaways" section because life doesn't have key takeaways.

I think about the bookshelf in my office. There are some non-fiction books I'm glad I read once. There are novels I've read five times and will read again. The novels keep yielding new insights because they contain genuine complexity, instead of a cherry-picked selection of simplified models. CS Lewis understood more about courage, friendship, temptation, and sacrifice than the combined authors of every book in the business section. He understood it the way you can only understand something when you build a world from scratch and watch how different souls navigate it.

Maybe students read fiction because they're not yet corrupted by the need to seem informed. Maybe the extremely smart read fiction because they've realized that seeming informed is worthless compared to actual understanding. And maybe the rest of us are stuck in the self-help aisle, hoping that some author has figured out the trick to living that we can learn in twelve chapters.

But Tolkien already told us the trick: the way is shut, and you have to walk it yourself.

(No amount of non-fiction can walk it for you.)

Every generation believes it is standing at the edge of the abyss.

That conviction has survived empires, religions, and revolutions, always wearing the local // current costume of despair.

The Mesopotamians wrote about moral rot and ecological exhaustion along the Tigris. Romans declared that their golden age was already behind them. The medieval chroniclers found signs of apocalypse in comets and crop failures. In the twentieth century, the mushroom cloud replaced the four horsemen. I grew up in the shadow of that cloud, and I remember adults talking about it as if it were an inevitability.

Today, the apocalypse is more algorithmic: climate collapse, runaway AI, or societal decay induced by screens and tribal politics.

The plot barely changes.

We have a recurring human superstition that our age is the terminal one - that we, by either sheer coincidence or luck or divine will, are alive for the final act of the play. It’s a superstition flatters and terrifies us in equal measure. We feel chosen by fate, even if what we’re chosen for is ruin.

Why do we cling to that belief?

Catastrophe is cognitively sexy. It simplifies the world into a single narrative: things are bad and things are getting worse. That’s easier to grasp than the truth: that progress and regression coexist. Psychologists call this the availability heuristic: we estimate the likelihood of events by how vividly we can imagine them. A single wildfire broadcast for days can outweigh decades of unseen reforestation. The bias tilts our emotional scales toward collapse.

There is another, subtle bias - status-quo pessimism. When we notice that something familiar is eroding, we assume decline is the default. The things improving often do so invisibly. When cholera vanishes, no one holds a parade. When antibiotics lose potency, it becomes a headline. The asymmetry breeds fatalism. If you live inside the information storm long enough, you begin to mistake noise for trend.

History, meanwhile, has an irritating way of disproving these intuitions. The “world” does sometimes collapse - societies fall, cities burn - but even then, the ruins become compost for new beginnings. The collapse of Rome didn’t end civilization; it reconfigured it. The Black Death didn’t extinguish Europe; it triggered a new paradigm of medical curiosity. Every age’s apocalypse has doubled as someone else’s foundation myth.

Our catastrophes have a habit of turning into uneasy bargains.

That doesn’t mean optimism is justified by default. Some of the old fears were rational. The Cold War really could have ended the species. Climate models and AI forecasts may yet prove grimly correct. But the repetitive emotional pattern tells us something about ourselves. We are drawn to doom not purely because it might happen, but because it makes us feel significant. To believe that history culminates with us is to deny our own smallness.

I don’t think it’s an accident that apocalyptic talk feels louder in the age of virality. The internet is a global empathy machine that happens to reward panic. Each tragedy, each crisis, each existential risk gets live-streamed into our retinas. The scale of it feels unprecedented because it is - not in reality, but in perception. It turns seven billion local anxieties into one shared emotional weather system. The result is a civilizational case of main character syndrome: everyone scrolling through the end of the world, starring themselves.

There are mornings when I read the headlines and think, maybe this really is it. Maybe the arc of civilization finally snapped. Then I recall that a Roman senator probably said the same thing while complaining about grain prices. The illusion of terminal uniqueness is hard to shake. We stand on the timeline and mistake the horizon for a wall.

Part of what keeps the pattern alive is that doom gives us moral clarity. When the world is ending, your priorities sharpen. You know who the villains are. You know what matters. There’s comfort in that. Believing in apocalypse is an ethical performance: it signals seriousness, compassion, responsibility. Saying "we’re doomed" feels braver than admitting you don’t know. Certainty, even dark certainty, feels adult.

There’s a narcissism baked into this. To imagine that we are the final witnesses of civilization is to elevate our own story above the billions before us. It makes us tragic protagonists instead of statistical accidents. That vanity is ancient too. Every culture, from the Aztecs to the Puritans, built myths around a cosmic finale. Our secular version substitutes science for prophecy, but the emotional logic remains: we want to be alive when it all happens, because that would make our lives matter on the grand stage.

When I look at the long arc of history, the boring truth dominates. Civilizations stumble, panic, reorganize, and continue. The shape of progress is less a line up and to the right, than a spiral - looping back, but a little higher each time. There are genuine catastrophes, but most are partial and reversible. Humanity keeps muddling through, inventing patches faster than it invents disasters. The fact that we’re still arguing about our imminent extinction after five thousand years of arguing about our imminent extinction should itself inspire a kind of stubborn hope.

Hope, of course, doesn’t photograph well. Catastrophe sells because it feels urgent, and urgency is attention’s predator. The ongoing story - the one where we slowly adapt, build, and recover - is too dull for timelines // virality. But dullness might be the miracle. Civilization is a process of continuously averting our own end.

Maybe we are special, maybe this really is the moment that decides everything. But history is full of people who thought that too. Odds are, we’re somewhere in the middle - not the last generation, just another one trying to survive its own fuckery.

That's less dramatic, I know.

But there’s something freeing about it.

If we are not the end, if this is not the end, we can stop rehearsing for the apocalypse and get back to the work of civilization: learning, repairing, and occasionally laughing at our recurring talent for doom.

Let me begin with a disclaimer: I don’t know everything. I have biases, blind spots, and the occasional compulsion to overexplain historical metaphors. But I’m going to do my best to make this interesting…

Every month, I keep my inbox informally open to questions from Pro members. I try to answer as many as I can privately, but occasionally, a handful of them deserve more room to breathe. So I’m adding a new Pro benefit.

This post is for you - the Pro members who sent in thoughtful questions over the past few weeks. Thank you. If you want to contribute to next month’s Q&A, feel free to email me at joan@joanwestenberg.com.

Below are a few of the best questions I’ve received this month.