How to figure out what you actually want when you've optimised for the wrong things

The question "what do you actually want?" sounds simple. It sounds like something you should be able to answer quickly, or at least honestly, given enough quiet time and the right journal prompt. Most career-change content is built on this assumption — that you already know what you want, you just need a framework to act on it. The discovery part is treated as solved.

For a lot of tech workers, it isn't solved. The problem is more prior than that: years of optimising for a particular set of outcomes has done something to the capacity to identify genuine preference — made it hard to hear, made it hard to trust, sometimes made it hard to believe it exists at all.

That's what I want to write about. Not how to find your purpose — that framing promises too much and I don't trust what it's selling. But what it actually feels like to try to want something authentically after years of wanting what you were supposed to want. Which is harder, and stranger, and lonelier than the framework-and-worksheet version of this process suggests.

What optimisation does to preference

When you enter a high-performing environment — and tech selects very hard for particular types of drive — you internalise a reward structure. Status, progression, compensation, scope, the prestige of the company name on your CV. These aren't arbitrary values. The environment reinforces them continuously: through who gets promoted, through what gets celebrated in all-hands meetings, through the implicit logic of every performance conversation you've ever had.

Over time — and this is the part that's easy to miss — these external metrics start to feel like preferences. You want the senior title. You want the high-visibility project. You want to be working on the thing that matters most. Except "want" is doing a lot of work there, because what's actually happened is that you've been trained toward these things so thoroughly that the training and the desire have become indistinguishable. You can't feel the seam between them.

The problem surfaces — usually painfully — when those things are achieved or removed and the felt sense of what you want doesn't clarify. You thought reaching the destination would tell you something true about yourself. Instead it tells you the destination was a proxy for something you haven't yet located.

That's an unsettling place to be. The career advice ecosystem doesn't have great tools for it, because the ecosystem assumes the problem is navigational. Here you are, there's where you want to go, let's talk about the route. The ecosystem is less useful when the problem is: I don't know where I want to go, and I'm not sure I know how to want things in a way I can trust.

The particular difficulty of this for tech workers

There's something specific about how this lands for people in tech that's worth naming.

The industry runs on a story about meritocracy — the idea that your position reflects something true about your intelligence, your effort, your worth. That story is flawed in all the obvious ways, but it also does something to identity: it makes your professional outcomes feel like genuine expressions of who you are, rather than products of the environment and the choices it made available to you. Which means when you start questioning the outcomes, it can feel like questioning yourself.

And tech attracts people who are good at optimisation — who find it genuinely satisfying to improve at things, to find efficiencies, to make systems work better. That orientation, applied to a career, produces impressive results. It also produces a tendency to treat the career itself as a system to be optimised rather than a life to be lived — which is a subtle but important difference, and one that becomes very visible when the optimisation stops producing the return you'd expected.

There's also the identity piece. If you've been the capable one, the senior engineer, the person others come to with hard problems — and then you step back from that, or it's taken from you, or you realise you don't want it anymore — you're not just changing jobs. You're dismantling the structure that told you who you were. Which is scarier than any spreadsheet about career transitions will capture.

What the search for genuine preference actually feels like

I want to be honest about this because most accounts make it sound cleaner than it is.

It doesn't feel like discovery. It doesn't feel like following a thread and arriving at a clear destination. It mostly feels like sitting with a silence that you're not sure has anything in it — and then, slowly, noticing something small. A recurring pull toward a particular kind of conversation. A thing you find yourself reading about when nobody's watching. An activity that makes time pass differently, not in a productive way, just in a present way. A person whose days you find yourself envying, not for their status but for what their days actually consist of.

These things feel too small. They don't feel like answers. They're not immediately usable in the way a purpose statement would be usable. And the pressure to have an answer — from other people, from yourself, from the part of your brain that is very uncomfortable with unresolved questions — makes it hard to let them be what they are: early signals, tentative, requiring patience rather than a decision.

The other thing that's hard about this — and I don't see it talked about honestly very often — is that finding your way toward something real often involves mourning the thing you're leaving behind. Not just the salary or the structure. The story. The version of yourself that knew who it was and where it was going and what the metric for success was. That version had its problems, which is why you're questioning it. But it was also coherent in a way that's genuinely hard to give up.

Grief doesn't feature heavily in most "finding your purpose" content. But it probably should.

What I've seen, and what I haven't

I've spoken to a lot of people in this place — some who've found their way to something that feels like theirs, some who are still in the middle of it, some who went back to a version of what they were doing before and found a way to hold it differently.

The ones who've found something real almost never describe a moment of clarity. They describe a gradual accumulation: something that kept coming up, that they kept dismissing, that eventually became impossible to dismiss. A low-stakes experiment that surprised them. A conversation that opened something they hadn't known was closed. A period of doing less and finding, in the reduced noise, that something faint had been there all along.

They also, almost without exception, describe the process as taking longer than they thought it would — and longer than they were comfortable with. The discomfort of not knowing, of being between identities, of not having a good answer to "what are you doing now" is real and persistent. It doesn't compress on demand. Trying to rush past it, in my observation, mostly produces decisions that have to be revisited later.

What I haven't seen is someone who found something genuine by following a framework to its conclusion. Not because frameworks are useless, but because genuine preference doesn't emerge from intellectual exercise. It emerges from doing things, from noticing how you actually respond rather than how you think you should, from giving the quiet signals enough time and enough silence to become audible.

That's not a satisfying answer. It doesn't package into a plan. But it's the most honest thing I know about this — and honesty, at this particular juncture, seems more useful than a cleaner story that turns out not to be true.

The identity track on the Start Here page has more writing on navigating this space — not from people who've solved it, but from people who know what it's like to be in the middle of it.