And it is genuinely impressive, so sit in the applause for a second before the obvious thing arrives, which is: you’re not on the bicycle. You’re watching. The bicycle is riding itself across the stage and you’re across the room from it, clapping, a spectator at the experience you were ostensibly there to buy.

This isn’t entirely hypothetical. Engineers have actually built bicycles that balance and ride themselves, as a flex, and it’s a real piece of work. I’m not dunking on the engineering. I’m dunking on the pitch — the part that sells it as a product that frees you from something. A self-balancing bike that helps you stay up is one thing: an assist, training wheels for grown-ups, fine. A bike that rides itself, with nobody on it, is a different kind of object, and the kind is “a solution that ate its own problem on the way to the stage.” That part is hypothetical but worth imagining, because it’s less ridiculous than it sounds.

The category error

A bicycle has exactly one part you can’t remove, and it’s you. Pedaling isn’t the regrettable cost of getting somewhere — you are the thing getting somewhere. And yes, in a dense city a bike is also the best transport there is, faster and saner than a car, which is why half of Amsterdam commutes on two wheels. But even then you’re on it; the getting-there includes you. The self-riding bicycle removes the rider, and that breaks both versions at once. If you came for the ride — the wind, the effort, the small animal competence of staying upright and turning your own body into forward motion — it automates away the exact thing you came for. If you came to get somewhere, it delivers the bicycle to your destination and leaves you standing in the driveway. You were never the friction in the picture. You were the cargo.

It doesn’t save labor; it deletes the purpose. The bike gets there. You stayed home and got nothing. The benefit has no recipient.

Means and ends

There’s a real distinction under the joke, and it makes the joke almost worth the absurdity, because it travels. Some activities are means: you do them to get an outcome, and if a machine can hand you the outcome and skip the doing, that’s pure gain. I do not want to wash dishes; I want clean dishes; the dishwasher is a small miracle and I have never once mourned the suds. Most of what we’re automating right now is means, and good riddance.

But some activities are ends: the doing is the outcome, the experience is the product, and there’s nothing left to hand you if you skip it. The bike ride. The meal you cooked for someone you love. The song you play yourself. The long conversation. The hike, as opposed to the arrival at the top of it. The self-riding bicycle is funny because it runs means-logic on an end. It treats riding a bike like dishwashing — a chore to be optimized — when riding a bike is the rarer thing where the chore was the point. Run that confusion at scale and you get a strange kind of progress: a world of flawlessly delivered outcomes that nobody is actually there for.

The default direction

Here’s the part that’s less funny and more worth your attention. Almost nobody decides, in cold blood, to automate away a joy. You wouldn’t actually buy the self-riding bike. The joke only works because the error is so obvious when it’s a bicycle.

The trouble is that the error is almost never obvious. Delegation has a default direction — toward more of it, always — because each individual step is reasonable and convenient and saves a little something real. And ends rarely announce themselves as ends; they wear the costume of chores. Cooking looks like a chore until the night you realize you haven’t made anything with your hands for anyone in a year. Writing the thing yourself looks like a chore until the part of your mind that used to do it goes quiet and you notice the quiet. My handwriting sucks, it didn’t used to, and I hate that. The self-riding bicycle is loud and stupid and easy to refuse. The version that actually gets you is silent: a hundred small, sensible handoffs, not one of them obviously the one that mattered, until you look up and find you’ve optimized the doing out of a life and kept only the having.

That non-recognition is the real subject. It’s the thing I keep circling, in the abstract: we automate away things we didn’t know we were keeping. The self-riding bicycle is what that looks like drawn with a crayon.

Where “it relocates upward” runs out

Those of us who build with AI tools have a comforting line we tell ourselves: the effort doesn’t vanish, it relocates upward. Hand the grunt work to the machine and your attention moves to higher-value judgment. I believe that. I’ll argue it repeatedly, because for means it’s true and it’s liberating.

It also has a floor, and the floor is exactly at the self-riding bicycle. There are activities with no higher altitude to relocate to, because they were never a stepping-stone to anything above them. The bike ride doesn’t ascend into some purer essence of cycling when you automate the pedaling. It just stops happening. The joy doesn’t move up a level. It evaporates. Comparative advantage is a wonderful instrument and it bottoms out precisely on the things that were ends. And forgetting that is how careful, well-meaning people automate their own lives hollow with the best intentions.

The chairs are the wrong scare

You already know the cartoon version: the people in the floating chairs, fed through straws, gone soft, gliding through a world that does everything for them. It’s a tidy image and it lets us all off the hook, because nobody pictures themselves in the WALL-E chair. Of course you’d never let it come to that.

But the chair is the wrong thing to be afraid of. Nobody chose the chair. They each chose a hundred reasonable conveniences, every one defensible on the day, and the chair is just where a road paved entirely with reasonable conveniences happens to end. The dystopia isn’t a decision; it’s an accumulation. That’s scarier than laziness, because laziness you can resolve to fix, but accumulation only asks you to keep saying yes to things that are, one at a time, completely fine.

Not an argument against tools

I want to be careful here, because it would be easy to read all this as anti-tool, and it isn’t. I use the latest tools, every day, on purpose; most of the other essays here are about doing exactly that and why it’s worth the cost. I am not telling you to pedal to the office on principle, or to scrub by hand what a machine scrubs better. The line is means-versus-ends, not more-versus-less, and the whole skill is noticing which one you’re holding before you hand it off. Automate every means you can reach. Guard the ends, because the ends are the part of the life that was ever actually yours.

And which activities are ends is yours to decide, not mine. For somebody, cycling really is pure transport and the self-riding bike would be a gift, assuming it comes with a sidecar you can ride in. For somebody else the commute is the best twenty minutes of the day. I can’t hand you the list, and I wouldn’t if I could — that was the whole point of Becoming Gnarly. All I’m claiming is that the list exists, that it’s shorter than the marketing would like, and that it’s worth drawing on purpose, in your own hand, before the default direction draws it for you.

The test

So here’s the test I’ve started using. It’s cheap and it works. When a tool offers to do something for you, ask whether you wanted the outcome or the doing. If it’s the outcome — clean dishes, a faster route across town, a draft of the boring memo — take the help and don’t look back. But if it’s the doing, if the doing was the thing you were actually there for, then what the tool is offering, very politely, is to be you at the one moment you most wanted to be yourself.

A bicycle that rides itself is not a better bicycle. It’s a very expensive way to not go on a bike ride.

The word I use for it is gnarly, which needs some defending, because to most people it lands as a surf-and-skate cartoon — a guy in board shorts, a turtle in sunglasses, a shaka hand sign. But the word has a second life the cartoon buried. A tree grows gnarled because it grew somewhere hard: wind, rock, exposure, a hundred seasons of not-quite-enough. The gnarl is the record of the struggle, and it’s also the reason the wood is strong and worth looking at. Smooth wood is young wood. The two meanings — gnarly the difficult, dangerous thing, and gnarled the weathered thing with character — are the same idea caught at opposite ends of a process. The difficulty going in is what produces the character coming out. That’s the whole thesis. The rest of this is me refusing to let it slip into being a fridge magnet.

The phrase itself, becoming gnarly, came out of a conversation about skateboarding with a close friend, and the grammar is the part I’d defend hardest. Not be gnarly. Not get gnarly. Becoming. You don’t arrive. In skateboarding there’s always a gnarlier line — a bigger gap, a taller wall, a scary trick that’s been made to look easy by everyone better than you. So the horizon keeps moving exactly as fast as you do. That sounds discouraging and is in fact the opposite. It means the thing can point a whole life in a direction without ever turning into a finish line you fail to cross. Chest-thumping needs an arrival. Becoming refuses one. It’s the most honest verb I know for a value, because it admits up front that you’ll die mid-sentence.

The receipts

A guy telling you to choose the hard path should have chosen a few, so here are mine. At seventeen I picked electrical engineering as my way into computers, and I picked it substantially because it was the hardest road to where I already knew I was going. I was right that it was the hardest — not kidding, I still occasionally have nightmares about exam failures, there were many. I’ve been collecting that kind of evidence ever since: forty-seven books written in the margins of a working life, a studio’s worth of products run by one person, and a stubborn habit of doing things myself well past the point where any efficient person would have hired it out. I am DIY to a fault. And I mean to a fault, because that phrase is going to matter shortly.

I have the literal version too. I’ve skateboarded long enough to have collected the surgeries and the scars that come with it, and somewhere along the way I came to prefer a scar to a tattoo — not as a rule for anyone, just as my own taste. A tattoo is a mark you have applied to mean something. A scar is one that got applied to you, against your will, by something that cost you. You don’t pick the design, the fall does. I even have a skateboard with my name on it — a “bro model,” which in skating is the affectionate joke grade between amateur and pro, the board they make for the guy who is emphatically not pro but earned the ribbing. That’s about the right altitude for all of this. Enough to have paid for the opinion. Not so much that I’d ever claim to have arrived. Becoming, not become or became.

Which is also, for the record, how I came to keep bees. In the things I do — skateboarding, mountain biking, the activities where gravity and the ground get to vote — injury is common enough that we have a name for what you take up while you heal: an injury hobby. A slam wrecked my shoulder badly enough to need surgery and a nine-month recovery, and nine months is a long time to sit still, so I went looking for somewhere to put the sidelined attention. Beekeeping sounded good, so I dove in. That’s the whole mechanism, and it’s gnarly all the way down: the hard thing hurts you, and instead of resting you go find another hard thing to be a beginner at. The bees in the backyard and the scars from the ramp are the same story — one’s just what I did while the other healed.

I left a part out of that story, and it matters more to me now than it did then. I kept at the bees for years — caught swarms by hand, ran as many as four hives at once, helped my dad with his. And most years I lost half of them anyway. I did the reading and went to the workshops and kept the operation as low-impact as I knew how, no chemicals and no gadgets thrown at the problem, the bees mostly left to be bees. They died all the same, for reasons I still can’t fully name; the science only half understands them and my backyard was never a controlled study. After enough seasons the little ecology project I loved had come to feel like an expensive way to kill a few thousand bees a year, and I stepped back. The break has lasted longer than I meant it to. I might keep bees again — that’s the becoming, too, the part where the next hard thing turns out to be the one that already beat you. For now I’m a beekeeper on hiatus, which is a more honest line than the one I opened with.

There’s an upside to being a beginner that I didn’t expect and now hunt for on purpose. The obvious half is humility, getting ego checked, and that’s real. The half nobody mentions is that mastery levies a tax: once you’re good, the freshness drains out and the work turns to maintenance and small increments. Starting over somewhere new refunds it — you get to be bad again, which is the only way to learn again in that steep, total way that only happens at the start. The price is an ego hit most people won’t pay, especially in public. At thirty I took up ice hockey: a near-pro-level skateboarder stumbling around the rink like he was trying to play basketball without knowing how to run, getting the puck poked off his stick by ten-year-olds. I loved it without reservation, exactly because I was terrible and there was that much open road ahead. Becoming, again — same verb.

Not long ago a surgeon went into my knee to fish out a loose body — a chip off my own kneecap that, his best guess, had been drifting around in there for years before it finally started to bite. He was trying to work out what set it loose, so he asked what I get up to. The skateboarding earned a raised eyebrow. But it was the fixed-gear bike that stopped him — I was midway through explaining how a fixie fights you on a descent, no freewheel, your legs braking against the cranks the whole way down a hill, when he just cut in: “Why?” Not the knee mechanics. Why ride that bike at all. I sat there a second and said, “Good question.” I didn’t have the answer loaded, and the not-having-it nagged at me a lot longer than the knee did. Most of what follows is me, belatedly, trying to give him one.

The claim, plainly

Most things worth having are earned through real effort, and the effort isn’t a tax on the having; it’s frequently part of the having. The struggle to assemble a thing is a lot of why the thing ends up yours. This is old and unglamorous and some version of it came from your grandmother, or maybe her grandmother. The reason it’s worth saying again, now, is that we’re living through the largest effort-removal project in human history, and “no pain, no gain” is too dumb a slogan to survive contact with it. It has to get smarter, fast, or we’ll automate away things we didn’t know we were keeping.

Because here’s the part the gym-poster version gets wrong, and the part I most want you to take with you: not all friction is formative. Some struggle builds you and some struggle just costs you, and the entire skill — the actual discipline this whole publication is about — is telling the two apart. A hard route up a rock face makes you a climber. A bad line at the DMV makes you nothing but late. Treating all difficulty as virtuous is how you end up romanticizing inconvenience, and that isn’t a philosophy, it’s a martyr complex with a podcast. The point was never the suffering. The point is the specific, chosen difficulty that runs along the grain of what you’re trying to become. Everything else is just friction, and friction with no formation in it is precisely what tools are for removing.

Which is the honest reason I’m not against tools, and why the essays that follow this one spend most of their time using the most powerful ones I’ve ever had. The line that matters isn’t human-versus-machine. It’s whether the difficulty you’re handing off was a means or an end. Delegate a means and you free yourself for the thing the means was always in service of. Delegate an end — automate the part that was the point — and you’ve deleted the thing while keeping its packaging. There is, I’m convinced, such a thing as a tool that performs your life on your behalf while you stand next to it and watch, and I’ll make that case at unreasonable length in the next essay. For now the principle is enough: keep the friction that forms you, shed the friction that only bills you, and accept that the work is knowing which is which — work that never fully resolves, which is the point.

The thing I can’t stop noticing

For most of history the central human difficulty was survival, and most of the species spent most of its effort on it. We have, for a meaningful slice of the world, largely solved that. And the people with the fewest imposed hardships turn out to be the ones reaching hardest for ever-more convenience — sanding away frictions so small we had to coin “first-world problems” to laugh at ourselves for minding them. I don’t think that’s decadence, exactly. I think it’s a muscle that doesn’t know what to do now that the thing it was built to push against is gone. We got the hardship removed and found we didn’t feel better, because some meaningful amount of who we are was assembled in the pushing. We were built to struggle.

Two things keep that observation from curdling into a lecture, and I hold to both hard.

First, this is about chosen difficulty, and I won’t romanticize the imposed kind. Hardship that picks you — poverty, illness, grief, the struggles nobody volunteered for — is not a growth opportunity, and telling someone in the middle of one that the friction is good for them is obscene. The entire value here lives in the choosing. Strip out the choice and it’s just suffering, and I have nothing to sell about suffering.

Second, which difficulties are worth choosing is radically personal, and I’m not handing out a list. Using a dishwasher is not a moral failure. I’m not going to grind my own flour to prove a point, and the fact that I’ll happily spend literally years to use hand tools to cut neighborhood mountain bike trails while ordering pizza delivered trailside so I don’t have to stop is not a contradiction — it’s the entire idea. You pick your hard things. The argument was never that you must suffer here rather than there. It’s only that there’s real value available in the struggle, that the value is easy to automate away by accident, and that it’s worth choosing some of it on purpose before the choosing gets done for you.

Why these essays sit together

That’s the through-line, and it’s why the writing here belongs in one place even when it doesn’t look like it. The essays I’m publishing first happen to be about making things in the AI era, because that’s the hard road in front of me right now and the one where the lines are being redrawn fastest. But the subject was never AI. AI is just the most dramatic instance, this decade, of the only question I find genuinely interesting: what’s worth doing the hard way, and how do you tell. Underneath the software and the studio talk, every one of these is an argument about which struggles to keep.

Here’s the moment that taught me what the word means, better than any intimidating trick I’ve fought to land on a board. Years back, a few of us were skating a deep concrete bowl at a public park, all of us decades in, fluent the way you only get from a lifetime of slams. A greenway loops that park, close enough that you hear the runners. We’d been clocking the same woman for weeks. What she was doing barely counted as running — a pace most people would beat at a walk — but the effort was enormous. You could see what it cost her just to get one foot past the other, every step hard-won, her whole body in it. And she kept showing up. Day after day, in public, at the stage where it’s hardest and pays back the least. One afternoon I nodded at her and said, “that’s so much fucking gnarlier than anything we do.” Nobody laughed. It wasn’t a joke and they knew it. Eleven feet of concrete isn’t nothing, but it’s a drop I’ve had forty years to make easy; what she was doing took a courage none of us were spending. I don’t know if she ever clocked the ragtag crew of overage skaters quietly in her corner, but I like to think being her cosmic fan club for a season counted for something.

I don’t expect to finish becoming gnarly. The process guarantees I won’t. The tree never stops being shaped by the weather. The line is always a little past where you are. You choose the next hard thing, you pay for it, you carry the mark, and you go looking for the one after that. The hard way isn’t always right. But often enough to organize a life around, it’s where the good stuff turns out to have been hiding.

So, welcome. Take the harder path when it’s the one worth taking. The rest of this is just me trying to work out which ones those are.