Finding Freedom Beyond the Career Ladder: A Personal Journey
There was a Monday in Dublin in my early twenties when I saw a senior colleague coming back from a meeting and I thought very clearly that I didn’t want his Monday to be perfect. He was good at his job, well paid, and well liked. He had the look, the title, the trajectory. I just looked at the next ten years of his calendar and could see mine sitting inside like a small box inside a larger one.
The Illusion of Freedom
It was the moment, or one of them. The funny thing is that at the time I would have told you that I was thinking about freedom. About escaping something. What I was really doing was assuming that freedom was a place one arrived at later, once a few more career ladders had been climbed and a few more boxes by 30 had been checked. Go for it, and the feeling lands. Finally relax into being a successful person.
What I noticed, in waves rather than all at once, was the opposite. The closest thing to freedom I found came not from finally getting more of what I was looking for, but from gradually losing interest in what I was supposed to be looking for in the first place.
Breaking Free and Exploring New Paths
So I left. The trip I had planned to take for a year ended up reshaping much of what followed: Vietnam, an ESL class, an adult language school that I ended up running, a self-made leather goods business, an online school that failed, a venture capital internship in my 30s where I moved from manager to intern, a coffee startup, and ultimately writing.
Looking at all of this, what stands out is not the variety. That’s how much I was still chasing something. I had left the obvious scenario and moved straight to another, the “Quit your job and build something” scenario, without really realizing I was there. I was reading Tim Ferriss and the rest of the canon on corporate exits at the time, and a lot of what I felt like “deciding my own life” was, in all honesty, doing what those books told me to do. From one script to another.
The Exhaustion of Comparison
The chase was not as noisy as expected. It wasn’t ambition in the fireworks sense. It was calmer. A constant pull toward the next thing, the cleaner version, the awesome version of the explanation you would give about yourself at a wedding. It was a tally of what your peers had that you didn’t. Friends who were already qualified accountants when I was thirty and became interns again. The house, the children, the “career qualified” box were checked. None of these things resulted in a major crisis. They came as a slow drip of “now I should…”
What I underestimated for a long time about all of this was the amount of energy it takes to keep going. Even when you’re not actively pursuing this step, you’re comparing yourself to it. You repeat the reasons why your version is also correct. You carry the little background dissonance of being slightly behind on someone else’s schedule. This ambient comparison is exhausting in a way that you only notice once it dawns.
Research Insights on Happiness and Maximization
Some of this also showed up in the language of research. A 2011 study by Iris Mauss and colleagues examined what happens when people place a high value on happiness. The authors concluded that “valuing happiness could be counterproductive, because the more people value happiness, the more likely they are to feel disappointed.” Their summary: “valuing happiness can lead people to be less happy even though happiness is within their reach”. It’s almost embarrassing how on-the-nose this is. Grabbing the thing pushes it further away.
Barry Schwartz and his colleagues approach the same problem from a different angle. Schwartz’s group classifies people into maximizers, who want to make sure every decision is the best possible, and satisficers, who set a bar and stop once something crosses 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 this one for a while. I had spent years maximizing my own life path, comparing every decision to an imagined optimal decision, scanning the terrain for the version of my choices that would have produced more.
A New Perspective on Freedom
The relief is not total. The “what if I had stayed in finance” continues to come in waves. There are weeks when I look at school friends who took the linear path, qualified, climbed, kept climbing, and I clearly see the gap. Some weeks, the observation is interesting; other weeks it’s a more pointed question. I’m really proud of those off-script years and I’m really aware of the path I didn’t take. Both of these may be true. Not chasing it is not the same as not noticing.
What has actually changed is closer to the distinction Schwartz highlights. The work I do now, writing, is something I always want to be good at. I always want to improve. The ambition has not evaporated. What has disappeared is the benefit of comparison. I don’t measure my morning against someone else’s in another field. I don’t manage a private ranking of the careers that have aged the best. Work matters; rank no longer exists, or at least not like it used to. This is what has the texture of freedom.
The Passage of Time and Acceptance
There’s also an age component to this, in all honesty. By the time you reach your mid-30s, a lot of the pressure from the 30s has already produced what it was going to do. The deadlines have passed. The people who were going to set milestones crossed them; people who weren’t, myself included, had to make peace with it or be unhappy. Choosing not to hunt, at this point, is partly a choice I made and partly a choice that was made for me over time. Both versions feel great.
I’m not a psychologist, so this is just one writer’s reading, but the honest story is this: the standardized milestone schedule is largely worth abandoning. Not softened, not balanced against the question of what you really want. Abandoned. Because in practice, the two questions are not really separable at the moment. The program is noisy enough that “what do I want” almost always arrives already shaped by “where am I behind,” and pretending you can clearly tell them apart is part of how the pursuit continues. Better to let go of the calendar first and let the other question come back, more slowly, with its own voice.
If any of this hits closer to home than is interesting, talking to a therapist or someone you trust is worth more than any article.
Ultimately, freedom isn’t what happens when you finally catch up with the version of your life that was supposed to make you feel arrived. This is what remains once you stop marking your days against this version. The score is prison. Install the dashboard.
Produced with the help of AI. Reviewed by the Silicon Canals editorial team before publication. Visit our about page.
About this article
This article is intended for general information and reflection. It is not intended as medical, mental health, or professional advice. The models described are based on published research and editorial observations, not clinical evaluation. If you experience a serious situation, speak to a qualified professional or local helpline. Editorial policy →
Here
“`
