I left a finance job in Ireland in my early twenties. The reason was simple enough at the time. I looked at the people ten and fifteen years ahead of me, the ones I was supposed to want to become, and I didn’t want to become them. So I moved to Vietnam, taught English, eventually ran an adult language school, tried a few businesses, and ended up writing.
From the outside that looked like drive. It looked like a person who knew his own mind and had the nerve to act on it.
Here is the part I’ve only admitted to myself slowly. I had read most of the leave-the-corporate-job canon by then. Tim Ferriss and the rest of the lifestyle-design shelf. The decision felt like mine, completely mine, and in a way it was. But it was also almost exactly what the books were telling me to do. I went off one script and straight onto another. I just didn’t notice, because the new one came with better lighting.
I’m not a psychologist, just someone who has read a fair bit on this and lived a version of it. The studies below are findings from particular groups of people, not settled science or rules about how your life has to go. Take them as something to think with, not instructions.
The exhaustion I’m describing isn’t the tired you feel after a hard week. That kind of tired is honest. This is slower and stranger. It’s the dawning sense, with no single dramatic scene attached, that a lot of the energy you’d been calling ambition was really approval, just wearing ambition’s clothes. There was no morning I woke up and knew. It seeped in.
The sharpest it ever bit me was around thirty. I’d gone from running a language school, a real thing with staff and students and a roof, to being an intern at a venture capital firm. An intern. Meanwhile peers my age back home were already qualified accountants with the letters after their names. On paper it was a status drop so steep it was almost funny, and at the time it didn’t feel funny at all. I remember the specific discomfort of it. But here’s the thing: the discomfort wasn’t really about the work. It was about how it looked. That should have told me something earlier than it did.
What fools you about the unconventional path is that choosing it feels like proof you’re being yourself. You turned left when everyone turned right, so surely you’re following your own compass. But picking the anti-default just gets you to a different aisle in the same shop. You’re still shopping.
The motivation research has a cleaner name for what’s going on underneath. Tim Kasser and Richard Ryan drew a line between intrinsic life goals, things like growth and connection, and extrinsic ones aimed at how you land in other people’s eyes. In a 1996 paper, they reported that “extrinsic aspirations for financial success, an appealing appearance, and social recognition were associated with lower vitality and self-actualization and more physical symptoms.” That’s one study, correlational, and it’s not saying chasing money makes you ill. But the shape of it is familiar. The catch is that “social recognition” doesn’t only mean the conventional kind. As Mick Cooper put it, extrinsic goals are “outcomes that are intended to heighten one’s standing in the eyes of others and to earn public admiration.” The admiration of a finance partner and the admiration of a roomful of digital nomads are different audiences, but the mechanism is identical. I wanted the second room to be impressed, and I’d convinced myself that wanting it was a form of courage. It wasn’t. It was the same hunger in different clothes.
That was the realization, and it took years to land.
The test I’ve landed on has nothing to do with whether a path looks conventional or unconventional. That distinction turns out to be useless. The question that actually holds up is whether you can give a real reason for what you’re doing, one that isn’t inherited and isn’t lifted from a book, and whether that reason survives a second asking. Not the first answer, which is always polished. The second one, when someone says “okay, but why that?” and you either have something or you don’t.
So here is where I’ve landed, at almost thirty-six. The second-asking test is the only one I trust now. Not whether the thing I’m doing looks brave or sensible from the outside, but whether I can say why I’m doing it twice in a row and still believe myself the second time. The language-school years pass that test. The intern stint, honestly, didn’t, and the exhaustion around it wasn’t a sign I was failing. It was the answer arriving on time.
That’s the part I’d push hardest. If the exhaustion is the slow, seeping kind I described at the start, treat it as information. It isn’t telling you that you’re weak, or ungrateful, or that you need to push through. It’s telling you whose script you’ve been running. The work after that is figuring out whether you’d write the same one yourself.
