Why Your Life Can Look Completely Fine and Still Feel Wrong

Seven years. That’s how long I stayed in a job that stopped making sense to me after about three.

I know. I know.

In my defence - and I do have one, it’s just not a very good one - I stayed because of a “bet”. The logic went something like this: if I stay long enough, get senior enough, then eventually the money, the flexibility, and the freedom to finally do things my way would materialise. There were also share options on the table, which is important to mention. The kind that, if the company ever sold (which was the plan), could have meant finally buying a house that I’d like (I can’t afford a decent one, and I’m picky). So I stayed. Wouldn’t you?

I also genuinely liked parts of it at first. Startups have this energy - informal, fast, everyone’s figuring it out together, everybody is doing many different things and not complaining. It was a perfect place to join straight after my graduation. You see, I couldn’t bear the thought of being Employee 275 doing one soulless task on repeat until retirement. In my mind, it was one or the other; nothing in between, so this felt like the alternative I needed. And a very interesting one.

So I worked hard. Obviously. The overtime was kind of part of the package. I’d get home exhausted, eat dinner, and then - and this is my favourite part - at 10 pm I’d open my laptop again. Not for the job, but for my own projects. The other things I was interested in doing, trying, and learning. I’d go until 2 am, sleep for five hours, wake up, and do the whole thing over again.

I genuinely thought I was living a great life. I would tell my friends things like “I’m so happy to be in the role I am, this is the best job, I’m learning so much…” The schedule was full; therefore, my life was full. That’s how it works, right?

No, it’s not.

Around year three or four, a more senior role came up in conversation. Real step up, looked great on “paper” (it was a discussion, not an actual offer) and the kind of thing you’re supposed to want. I thought about it. It sounded great in theory, but I decided not to go after it. You see, I was informed where this role would lead, and it wasn’t what I was building my life toward. I wanted more flexibility, the ability to choose my own hours, work remotely when I want to, and work less but on higher-value things. The role would have given me none of that. In fact, the opposite: more hours, more presence and visibility, even further from the flexible remote life I thought I was slowly, carefully moving toward. So I decided not to show much interest and just keep doing what I was doing. Which was approximately six years of being in the same role, that I landed after my first promotion, after year one. :)

Except - and here’s the fun part - that path also didn’t go anywhere.

The flexibility never arrived. The autonomy I’d imagined didn’t come. The share options continued to stay on the horizon. Every year, I thought this might be the year and every year it wasn’t, in fact, the year. At some point, “patient and strategic” starts to look a lot like “waiting for something that’s never actually coming” - and I was deep in year five before I was willing to admit that to myself.

The sense of misery wasn’t dramatic, I should say. It felt more like a low hum of wrongness that I couldn’t quite locate. Everything on paper was fine. I had lovely friends, a kind long-term partner, a healthy family, an alright salary, a place to live, and a job. I had nothing to complain about, which somehow made it worse, because I was clearly complaining, just internally, constantly, about something I couldn’t understand myself.

So I did what any reasonable overthinker does - every personality test on the internet. :) Myers-Briggs, the Enneagram, Human Design, Big Five, a brief and slightly embarrassing detour into numerology and Vedic astrology and whatnot. I journaled. I meditated. I read hundreds of essays written by people who’d figured their lives out at twenty-four and wanted to tell me all about it.

They all said very similar things, but I ignored all of them. Of course I did. It was their life and their lessons, not mine. :)

Eventually, I made a list of what I felt I wanted: to live somewhere warm and sunny, and with beautiful nature close by, flexible work hours, preferably remote, meaningful work, more time for the things I loved, and the general feeling of being a person I wanted to be. I decided my core value was freedom. And it made sense: freedom was the key, money was the door, and once I had enough of both, everything else would automatically sort itself out.

Sounds like a solid plan, and I thought I was kind of following it.

Here is what I actually did: stayed at a startup for seven years, earned less than most people I knew, worked more hours than most people I knew, and lived in Scotland, which is extremely beautiful, but is not what anyone pictures when they hear somewhere warm and sunny. I decided not to pursue the one role that might have at least changed something. Turns out, I waited for conditions that weren’t coming and called it a strategy, but I’m sure my closest people quietly called me stupid.

It was a very well-reasoned way of not doing anything to get the things I wanted.

Values vs. Preferences & Why the Difference Matters

Here’s the thing I eventually figured out, much later than I’d like to admit.

The problem wasn’t that I didn’t know myself. I actually knew myself reasonably well. The problem was that I had absolutely no idea what my values were, because I’d been confusing them with my preferences for years, and they felt identical from the inside.

Let me explain.

The psychologist Milton Rokeach described values as enduring beliefs, not the things that show up when life is easy, but the things that organise your behaviour when it isn’t. When choosing them costs you something. A preference is different. A preference is what you reach for when conditions allow. Both are real and both matter, but they are just not the same.

Preferences are negotiable. You can live against a preference for a long time - the loud office, the early meetings, the weather that you don’t really love - and remain yourself. Annoyed, yes. Plotting your escape, sure. But still yourself.

Values are different. When you live against a core value for long enough, something more serious starts happening. You begin to feel like you’re slowly disappearing into a version of yourself you never actually chose. The philosopher Harry Frankfurt put it like this: there’s a difference between wanting something and endorsing what you want. Preferences live at the first level. Values live at the second - things you’d still choose after real reflection, things that when you act against them produce not just frustration but a specific and heavy friction - the feeling that you’ve betrayed something in yourself.

That friction is an important piece of data. Most of us, of course, dismiss it. We call it overthinking, perfectionism, and being ungrateful for what we have. What nobody tells you is that it’s actually pointing at something real that needs to be investigated.

What I eventually found, past the preference for freedom, was something harder to name: agency. Not the flexible hours or the remote work or the sunny location - those were the conditions I wanted the agency to deliver. The actual value was simpler and more fundamental. The need to have real authorship over my own direction. To make choices that were genuinely mine, not a slow accumulation of decisions made by default, or in service of a “bet” that was probably never going to pay out.

You can’t wait for the agency to arrive with the right title or the right exit event. If you don’t consciously choose where you already are, someone else will show you how to live. So it turns out you just have to choose it. Which is annoying, but there it is.

Four Questions to Find Your Actual Values

Now, I don’t want this story to be about me. I want it to be useful to you, so you can notice when you’re not living in alignment with your values. And if you decide to spend 10 honest minutes in peace and quiet today, you should ask yourself these questions:

1. What do you keep choosing, even when it costs you something? Look at the last six to twelve months. What did you choose consistently, even when it was inconvenient, unpaid, or exhausting? The things you keep choosing under pressure are closer to your real values than anything you’d put on a list on a good day. For me, it was my passion projects that I did from 10 pm to 2 am. They mattered to me because I could bring my vision to life in ways I personally wanted.

2. When have you felt that deep friction, the feeling of betraying yourself? Think of a time you said yes when every part of you wanted to say no. A role you stayed in too long. A version of yourself you kept performing for an audience that didn’t even ask for it. What was actually being violated? Name it as specifically as you can. For me, it was spending most of my life at a job that was no longer working for me. Feeling stuck and unable to move in any direction that I wanted.

3. What would you refuse to trade, even for something you really want? Imagine something appealing - more money, more security, more status - but with a condition attached. What conditions would make you say no, regardless of how good the upside looks? The non-negotiables are your values. The things you’d trade without much internal debate are your preferences. I’d personally refuse all of these things if it meant that I have to perform a character that I am not just to justify them.

4. What did you inherit versus what did you actually choose? Many of the values we walk around with were never ours to begin with. They were handed to us by family, by culture, by whatever environment we stayed in long enough that its logic started to feel like our own. Ask yourself honestly: if nobody in my life had any opinion about this, would I still choose it? If the answer is no - that’s useful information. It doesn’t mean you have to throw it out right away, but now you can decide whether you actually want to hold onto it. For example, I was hoping to eventually achieve a senior enough role, a house, and loads of money, etc., because society made me believe this is what success looks like, and I obviously didn’t want to fail at life. But when I started to ask myself the hard questions, I understood that success to me was having agency, having autonomy, having meaningful relationships, and expressing myself in ways I wanted to, and I don’t need more money, more status, a house, or a senior role to do those things. In my head, I’m already kind of successful in life in more ways than one.

What You’re Looking For

You’re not looking for a tidy list of five inspiring words (which is useful to have, by the way). You’re looking for a small number of things that show up consistently across all four questions: things you keep choosing, things whose absence creates the friction you can’t ignore, things you’d protect even at a cost, things that feel yours rather than borrowed from someone else’s mind.

Those are your values (most likely, not a guarantee).

And everything else - the flexibility, the freedom, the warmth - might be real and important preferences absolutely worth building your life around, but they are not necessarily your values. Once you can see the difference, you can actually design around both. A life with your values at the foundation, and your preferences as the conditions you’re actively building toward.

That’s a much more interesting problem to work on than “find your passion.” You can, of course, trust me. I spent seven years trying to figure this out for myself. :)