The company is sold. The money has landed, and it's more than they could ever spend. The house, the car, the travel – everything that used to require a plan, a budget, or a sacrifice can now simply be bought. And there's still plenty left over. It ought to be the end of a happy story. Yet it's surprisingly common that what follows isn't happiness, but emptiness. The question I want to think through is this: what is actually driving us once the result is no longer hard to get?
01 · The idea
The entrepreneur who won
The psychologist Tal Ben-Shahar has a name for the phenomenon: the arrival fallacy. The belief that we'll be happy once we reach the goal. My sense is that what actually carried us was rarely the goal, but the road there. It gave the days structure, an identity to lean on, and a direction. Once the goal is reached, all of that disappears at once, and what's left is a fairly naked question: what do I do now, and why?
That so many people who've made a big exit start something new, even though they never have to work again, probably says something. The money was rarely the drive itself. It was the scoreboard in a game that was fun to play.
02 · An old problem
Keynes saw it coming
The question is older than the startup world. In 1930, John Maynard Keynes wrote an essay about how his grandchildren's generation would live. He believed humanity would one day solve the economic problem – and that we would then face our real problem: what to do with the freedom. He wasn't particularly confident we'd handle it well.
Almost fifty years later, the philosopher Bernard Suits gave an unexpected answer to the same question. He described playing a game as a voluntary attempt to get past obstacles that aren't really necessary. In the same book he imagined a utopia where every need was already met – and concluded that games might be the only thing still worth doing.
03 · What the resistance gave
Maybe a journey is a bit of an iceberg
What's visible from the outside is the exit: the number in the press release, the newspaper article, the new life. But below the surface is everything the years of building actually provided.
Csikszentmihalyi's research on flow offers a clue. We seem to be at our best when the challenge sits right at the level of our ability – hard enough to demand everything, possible enough to be within reach. A company being built is almost a flow machine. A bank account full of money is not.
When the exit arrives, it isn't just the job that disappears. Everything below the surface goes at the same time.
04 · Voluntary difficulty
The difficulty may not need to be necessary
Chess is the clearest example I can think of. Computers have beaten the best humans for close to 30 years, and yet chess has arguably never been more popular. Nobody plays to produce the best move – the engine does that in milliseconds. You play because you're the one doing the thinking.
Same thing with the woodworker who builds their own furniture even though IKEA exists, or the runner who runs the ten kilometers even though the bus is faster.
What they have in common seems to be that the difficulty is no longer necessary – and is still worth something. That's exactly Suits's point. So maybe the way out for the entrepreneur isn't finding something that has to be done, but something worth doing even though it doesn't. A new game, rather than more points.
05 · The parallel
My own, considerably smaller exit
I've never sold a company, and this post didn't start out being about me. But the more I've thought about the entrepreneur, the more I've recognized something in my own day-to-day as a software developer.
I've always kept a list of things I want to build for myself. A tool here, a small service there, something that's been bugging me for a while. The list used to be long because time was short. Now it isn't the implementation that stops me. With AI, most things on that list can be described and running the same evening. Oddly enough, that has made me less eager, not more.
And there an uncomfortable thought shows up: if everything cool I might build is that easy to build, couldn't somebody else just as well build it? What's supposed to motivate me then?
I think it's fundamentally the same mechanism as for the entrepreneur. Money removes the resistance in getting things. AI removes the resistance in doing things. In both cases it suddenly becomes clear how much of the meaning was in the difficulty itself.
And the thought that somebody else could just as well build it has, if I'm honest, almost always been true. There has essentially always been someone capable of building the same thing, and often someone already had. What made my projects unique was never that nobody else could. It was that they were mine – chosen by me, shaped to my needs, with every part comprehensible to me.
And voluntary difficulty is, if Suits was right, precisely what a game is.
06 · A suggested order
Four questions before I start building
The question “can I build this?” now almost always has the answer yes, so it doesn't tell me much anymore. Instead, you could walk through four steps. The order isn't a truth – mostly a way to make the choice deliberate.
07 · A few projects I'm curious about
Not everything needs the same treatment
Tools I just want to have
A script that sorts receipts, a little dashboard for the house. Here the result was the whole point. Let AI take it and spend the evenings on something else.
The thing I want to understand
That idea for my own small interpreter or database engine. Not because the world needs another one, but because I want to know how it actually works.
What used to be too big
When implementation gets cheap, ambition can grow. Projects that used to be unreasonable for one person may not be anymore.
The thing that's for someone else
Something for the family, a club, or a community. Meaning seems to grow when more than just me benefits from the result.
Getting stuck now and then
That uncomfortable moment when nothing works. I suspect that's where most of the learning sits, and that it can be worth not asking the AI straight away.
What was mostly about being productive
If the appetite vanishes as soon as something becomes easy, maybe the project was mostly a way to feel competent. No wonder it loses its shine.
08 · Where the value lands
If this holds, the value moves to judgment
My thought is that when implementation gets cheap, the value moves somewhere else. The question is no longer “can I build this?” but “what is worth building?” Taste, problem selection, and the ability to see what's actually needed could become the scarce resource. The entrepreneur faces the same thing, really: once money is no longer scarce, the question becomes what is worth spending it – and yourself – on. But that's of course an assumption that needs testing.
| When the resistance disappears from… | We might get… | But only if… |
|---|---|---|
| Mechanical work | More time for the parts that are actually interesting | We choose to spend the time there, and not just on more projects |
| The threshold to get started | More ideas that actually get tried | We don't confuse volume with meaning |
| The necessity of doing it yourself | Freedom to do things because we want to | We find a reason other than having to |
| The scarcity of implementation | More room for judgment and taste | We dare to trust our own taste |
09 · How far I've gotten
Maybe it's about choosing your resistance
Viktor Frankl held that we find meaning in three ways: through what we create, through what we experience and those we love, and through how we relate to what we cannot change. It strikes me that neither money nor AI touches the last two very much. And the first hasn't disappeared. It has changed shape.
I see no point in turning “build everything yourself” into a creed. AI is a fantastic tool, and it would be strange to pretend otherwise. But I do think there's something to making the resistance deliberate.
Maybe the same goes for those of us who build things. The tool I just want to have can just as well be generated. The problem I want to understand can be mine. And some projects may not survive the question of why I wanted to do them – which doesn't have to be a problem. Maybe the energy wants to go somewhere else.