There was a Tuesday in Dublin, sometime in my early twenties, when I watched a senior colleague walk back from a meeting and thought, very clearly, that I did not want his Tuesday. Nothing was wrong with him. He was good at the work, well-paid, well-regarded. He had the suit, the title, the trajectory. I just looked at the next ten years of his calendar and could see mine sitting inside it like a smaller box inside a larger one.
That was the moment, or one of them. The funny thing is, at the time I would have told you I was thinking about freedom. About escaping something. What I was actually doing was assuming freedom was a place you arrived at later, once a few more career rungs were climbed and a few more by-30 boxes were ticked. Get there, and the feeling lands. Finally relax into being someone who had made it.
What I’ve noticed, in waves rather than all at once, is the opposite. The closest thing to freedom I’ve found has come not from finally getting more of what I was after, but from gradually losing interest in what I was supposed to be after in the first place.
So I left.
The trip I planned to take for a year ended up reshaping a lot of what came after: Vietnam, an ESL classroom, an adult language school I ended up running, a self-taught leather side business, a failed online school, a venture-capital internship in my thirties where I went from manager back to intern, a coffee startup, and eventually writing.
Looking back at all of that, what stands out is not the variety. It’s how much of it I was still chasing something. I’d left the obvious script and walked straight onto another one, the leave-your-job-and-build-something script, without quite realizing I was on it. I was reading Tim Ferriss and the rest of the leave-the-corporate-job canon at the time, and a lot of what I felt was “deciding my own life” was, in fairness, doing what those books were telling me to do. Off one script, onto another.
The chase didn’t get loud the way you’d expect. It wasn’t ambition in some firework sense. It was quieter. A steady pull toward the next thing, the cleaner version, the impressive-sounding version of the explanation you’d give about yourself at a wedding. It was the running tally of what your peers had that you didn’t. The friends who were already qualified accountants while I was thirty-ish and back to being an intern. The house, the kids, the qualified-in-a-career box ticked. None of these things showed up as one big crisis. They showed up as a slow drip of “by now I should…”
The part of all this I underestimated for a long time is how much energy the chase takes. Even when you’re not actively pursuing the milestone, you’re checking yourself against it. You’re rehearsing the case for why your version is also fine. You’re carrying the small humming background dissonance of being slightly behind on someone else’s schedule. That ambient comparison is exhausting in a way you only notice once it lifts.
Some of this has shown up in research language too. A 2011 study by Iris Mauss and colleagues looked at what happens when people place a high value on being happy. The authors concluded that “valuing happiness could be self-defeating, because the more people value happiness, the more likely they will feel disappointed.” Their summary line: “valuing happiness may lead people to be less happy just when happiness is within reach.” It is almost embarrassing how on the nose that is. The act of grasping at the thing pushes it further away.
A different angle on the same problem comes from Barry Schwartz and colleagues. Schwartz’s group sorts people into maximizers, who want to be sure every decision was the best one available, and satisficers, who set a bar and stop once something clears it. Across seven samples, they reported “negative correlations between maximization and happiness, optimism, self-esteem, and life satisfaction, and positive correlations between maximization and depression, perfectionism, and regret.” I sat with that one for a while. I had spent years being a maximizer about my own life path, checking each decision against an imagined optimal one, scanning the field for the version of my choices that would have produced more.
The relief isn’t total. The “what if I’d stayed in finance” voice still bites in waves. There are weeks where I look at friends from school who took the linear path, qualified, climbed, kept climbing, and I notice the gap clearly. Some weeks the noticing is interesting; other weeks it’s a sharper kind of question. I am genuinely proud of the off-script years, and I am genuinely aware of the road I didn’t take. Both of those can be true. Not chasing isn’t the same as not noticing.
What has actually shifted is closer to the distinction Schwartz is pointing at. The work I do now, writing, is something I still want to be good at. I still care about getting better. The ambition has not evaporated. What’s dropped off is the comparison-edge. I’m not measuring my morning against someone else’s morning in another field. I’m not running a private league table on whose career has aged better. The work matters; the rank doesn’t, or at least not in the way it used to. That’s the bit that has the texture of freedom.
There’s an age component to this as well, in fairness. By the time you’re staring at the back half of your thirties, a lot of the by-30 pressure has already done what it was going to do. The deadlines have passed. The people who were going to make the milestones have made them; the people who weren’t, including me, have had to make peace with that or be miserable. Choosing not to chase, at this point, is partly a choice I’ve made and partly a choice that’s been made for me by the passing of time. Both versions feel fine.
I’m not a psychologist, so this is just one writer’s read, but the honest version is this: the standardized milestone schedule is mostly worth abandoning. Not softened, not balanced against the question of what you actually want. Abandoned. Because in practice the two questions aren’t really separable in the moment. The schedule is loud enough that “what do I want” almost always arrives already shaped by “where am I behind,” and pretending you can cleanly tell them apart is part of how the chase keeps running. Better to drop the schedule first and let the other question come back, slower, in its own voice.
If any of this is landing closer to home than it is interesting, speaking to a therapist or someone you trust is worth more than any article.
Freedom, in the end, isn’t what arrives when you finally catch up to the version of your life that was supposed to make you feel arrived. It’s what’s left once you stop scoring your days against that version at all. The scoring is the prison. Put down the scorecard.
Produced with AI assistance. Reviewed by the Silicon Canals editorial team before publication. See our about page.
About this article
This article is for general information and reflection. It is not medical, mental-health, or professional advice. The patterns described draw on published research and editorial observation, not clinical assessment. If you’re dealing with a serious situation, speak with a qualified professional or local support service. Editorial policy →
