Freedom Was Never the Point

I spent seven years in a job that stopped making sense to me after about three.

Which is a strange thing to admit, because it took me another two years to understand why - and then another two to convince myself that enough was actually enough and it was time to leave.

I’m not proud of the maths.

For most of that time, I worked without breaks and stayed late. It was a startup - that was the culture, that was the expectation, and honestly, I didn’t even mind it at first. I liked how informal it was, and I couldn’t bear the thought of being Employee 275, doing one specific, soulless thing all day. In my mind, it was one or the other; nothing in between. So I’d put in my hours, get home exhausted, eat dinner, and then at 10pm open my laptop again - not for the job, but for my own side projects. Things I actually cared about. I’d stay up until 2am doing that, then sleep, wake up, and repeat the whole thing all over again.

I thought I was living well. I felt productive, hardworking, sort of admirably driven. There was something that felt aspirational about the busyness, as if the fullness of the schedule was proof that my life was full, too.

In reality, I had no life. I was just very, very confused.

Around year four or five, the confusion got noticeably louder. You see, I’ve always been pretty introspective - the kind of person who finds self-knowledge very interesting. But at that time, it became something else. Something that, if a good friend described it to me, I’d suggest they talk to someone. :) I did every personality test I could find. Some of them several times. I tried astrology, numerology, chiromancy and a variety of other things that promised to tell me something about myself I didn’t already know - even though I didn’t believe any of them.

Strangely, almost all of them told me very similar things, but that’s another story.

I meditated. I attempted journaling. I did visualisations, exercises, and read other people’s stories. I was searching for an answer to a question I hadn’t even fully formed yet. I just knew something was wrong, but I couldn’t name it. There was a persistent sense of “wrongness”, even though my life, by any reasonable measure, looked completely fine.

I practised gratitude. And on paper, it worked perfectly - I had enough money, a decent place to live, I was fit and healthy, had a loving family, lovely friends, a solid long-term partner that was kind to me, and no enemies as far as I was aware. There was objectively nothing wrong, and yet I felt somewhat empty inside. Things felt wrong, and I was stuck.

How dare I feel that way? Which, of course, made me feel worse. :)

So I decided to make a list of things I wanted.

I wanted to live somewhere warm and sunny, with beautiful nature. I wanted to choose my own hours and work on projects I actually cared about. I wanted to help people and feel that I brought real value to the world. I wanted a bigger, nicer place to live, more money to travel, and more room for hobbies instead of saving for the future. And above all, I wanted freedom - to be and do as I pleased, when I pleased, and how I pleased.

I convinced myself that freedom was my core value. It made perfect sense: if I had freedom, I could automatically have everything else on the list. Freedom was the key, money was the door, and I just needed to get more of both to get the life I wanted.

But here’s what I actually did...

I chose to work at a startup for seven years, earning less than anyone I knew while carrying more stress and longer hours than most. I moved to Scotland - very beautiful nature, yes, but also some of the most reliably grey and rainy weather in Europe. I stayed in the role that would never pay me enough to save for the bigger life I kept describing to my partner in detail - who, I’d say, was surprisingly patient about hearing it. I said I wanted to help people, but I spent my days ensuring that new products reached people on time so they could try them and eventually buy them.

We were introducing new products to people, so that’s good... right? They need it, right?

I’m laughing a little as I write this. This is genuinely what I’d tell myself when the question about meaning would pop up in my head.

As you can see, the gap between what I said I valued and what I actually kept choosing was not that subtle. It was not a minor inconsistency or a small misalignment. It was seven years wide, chosen when I was young and didn’t know better, and then chosen again, every year, seven years in a row.

Values vs. Preferences

Here’s what I eventually understood, much later than I’d like to admit.

The problem wasn’t that I didn’t know myself. The problem was that I confused my values with my preferences and treated them as the same kind of thing.

The psychologist Milton Rokeach described values as enduring beliefs. By his definition, a value is not something that shows up when it’s convenient - it’s something that organises our behaviour when it isn’t, when conditions are uncomfortable, when choosing it costs us something. A preference, on the other hand, is what we reach for when conditions are comfortable. This confusion - values as the things we want versus values as the things we keep demonstrating - is probably one of the most expensive mistakes people carry into the project of designing their lives.

It seems easy to distinguish the two at first glance. When it comes to values exercises, we usually get a list of words that sound nice, and we circle the ones that resonate. We select things like Kindness, Autonomy, Freedom, and assume they are our values. While they do deeply resonate, they are not necessarily our values - they can also simply be our preferences, aspirations, and things we truly believe should be real and true in our lives if conditions are good enough.

The real test is what happens when we’re under pressure. When we investigate our lives and check what we keep choosing when it costs us something.

The philosopher Harry Frankfurt separated first-order desires (wanting something) from second-order desires (caring about what you want - wanting to want certain things). He argued that what makes us distinctively human isn’t our capacity to have desires, but our ability to reflect on them and identify with them at a deeper level.

A preference operates at the first-order level. We want the comfort, the approval, the familiarity. A value operates at the second-order level. It’s not just something we want, but something we endorse wanting. Something we’d still choose after deep reflection. Something that, when we act against it, produces not just disappointment but a very strong internal friction - the feeling that we have somehow betrayed ourselves.

That friction is the diagnostic. It’s something that signals that we’re violating something we didn’t even know we were protecting.

Most of us have been trained to reframe the friction as perfectionism, overthinking, or ingratitude for what we have. What we’re rarely taught is that friction is actually an important piece of information that something isn’t fully aligned with what we need. Only when we start examining the friction we feel can we begin to understand what we actually care about. The psychologist Shalom Schwartz found that people’s stated values and enacted values diverge in systematic, predictable ways. What people say they value and what they repeatedly demonstrate they value are often different things.

And so when we sit down to examine our values, we aren’t just excavating what is ours, but we’re also sorting through a mix of genuine values, aspirational values, inherited values, and preferences that look and feel like values. The sorting requires a level of honesty most of us aren’t willing or even capable of giving ourselves.

Many of the values we carry around were never ours to begin with. They were handed to us by family, by education, by the cultural environment we grew up in, by the work we’ve done long enough that its logic started to feel like our own.

So the question is not: “What sounds like me ?” but “What have I kept demonstrating, even when I didn’t mean to?”

Which brings me back to the question I haven’t answered yet.

If I felt that my values were unmet, why did I stay for several years?

That’s because people don’t leave situations when their values are unmet right away. They leave when the pain of staying finally exceeds the fear of leaving. It’s a slow, invisible, and accumulating process that we don’t notice until one day it becomes so loud that we can no longer take it.

Preferences are negotiable in a way that values are not. We can live against a preference for a season - work the loud office, take the early meeting, tolerate the difficult environment - without losing ourselves. We’ll hate it, and we’ll want to change it, but it won’t affect our sense of who we are.

But values are different. When we live against our core values for long enough, we start to feel like we’re disappearing into a void. Becoming competent at a life that isn’t ours. We feel miserable in a way we can’t explain, because from the outside, everything looks completely fine.

That feeling isn’t ingratitude. And it’s not overthinking or a failure to appreciate what we have. It’s more like a signal telling us that we’ve been living at the preference level while our values are being persistently unmet.

So what were my actual values?

Not freedom on its own, apparently. I wanted freedom because of what it promised on the other side of the door.

And what was on the other side, it turned out, had nothing to do with sunny location or hours or money. These are my very strong preferences - very real, important, and worth pursuing - but not worth disappearing for.

What I actually needed was simpler and harder to name clearly at the same time. It was about being free to show up as the full-volume version of myself and not being asked to turn it down. To do work I actually care about, not work I was told to value and care about, and to know that my preferences, instincts, and judgment counted.

You see, I had options at the company, and if I waited long enough, I might have seen a small fraction of the money, which I thought could have helped me get closer to the freedom I was after. That was the hope, anyway. What I hadn’t understood then - and do now - was that I was waiting for external conditions to give me something I could actually choose right now, by doing my own thing and placing myself in environments where I felt safe enough to be it.

I know now what compromises I can make and what things aren’t up for negotiation. I know what I’ll keep working toward and what I’m no longer willing to trade away to get there.

It just took me longer to learn it than I’d have liked.