Imperfect Club

Imperfect Club

When good work stops feeling like yours

On the quiet misalignment between competence and fit — and three honest questions that help you see what's actually happening

Ricky Tam's avatar
Ricky Tam
May 22, 2026
∙ Paid

I want to describe a specific kind of professional experience that rarely gets named directly.

Not burnout. Burnout is about depletion — running on empty after running too long.

Not imposter syndrome. That’s about doubting whether you deserve to be here.

Not a career crisis. That implies something dramatic, a breaking point, a moment of collapse.

This is quieter than any of those. It’s the experience of being genuinely good at something that has quietly stopped fitting the person you’ve become.

You’re competent. You know you’re competent. The evidence is consistent and visible. And somewhere between the last performance review and this morning, the work stopped generating the feeling you thought competence was supposed to generate.


Three versions of the same experience

Because this shows up in different forms, and the version you’re in determines what actually helps.

The promoted ceiling.

You worked towards a role for years. The progression was deliberate and earned. And then you got there — and discovered that the role is a completely different kind of work from the job you loved.

The job you loved was the doing. The craft, the making, the solving. The role is the managing. The reporting. The performance of leadership that comes with the title.

You’re good at the role. You’ve developed the skills. But the thing that used to energise you — the actual work, the hands-on version — is now something you supervise rather than do.

This isn’t failure. It’s a structural consequence of progression in most organisations. The people who are best at doing get promoted into not doing. And almost nobody warns you that this might not be what you wanted.

The competence trap.

You got very good at something. Better than most people around you. And then you stayed.

Not because you love it. Because leaving felt wasteful. Because the competence is real and starting again feels like choosing to lose something you earned. Because the identity you’ve built over years is tied to this particular skill, and releasing the skill means releasing the identity.

So you keep doing the thing.

And the thing keeps not being quite right.

The competence trap is particularly common in high-achievers because high-achievers are, by definition, people who became very good at things. The same quality that made them effective is the quality that holds them in place.

The quiet drift.

This is the most common version and the least dramatic. Nothing changed. There was no promotion, no moment of realisation, no obvious turning point.

The work just gradually stopped generating what it used to generate. You used to leave energised. Now you leave fine. The work is adequate. The income is reasonable. The colleagues are decent. There’s nothing obviously wrong.

Fine is not the same as good. But fine is easy to miss. And by the time you notice the drift, you’re usually quite far from where you started.


Why this is hard to name

The reason this experience rarely gets spoken out loud is that it sounds, from the outside, like ingratitude.

You have a good job. You’re good at it. You’re paid reasonably. What exactly is the problem?

The problem is that ‘the problem’ is the wrong frame. This isn’t about problems. It’s about fit. And fit, unlike problems, doesn’t have a straightforward solution.

Fit is the relationship between the work and the person doing it. A job that fits perfectly at thirty might not fit at forty. Not because the job changed. Because you did. You developed, expanded, shifted in emphasis. The work stayed the same. The misalignment emerged slowly, without announcement.

Naming this isn’t ingratitude. It’s accuracy.


What actually helps — three honest questions

These aren’t designed to push you towards any particular outcome. They’re designed to help you see more clearly what’s actually happening, which is the only honest starting point.

If you could stop doing this tomorrow with no consequences — financial, relational, identity-related — would you?

Not: should you. Not: is it realistic. Just: would you?

Most people who answer yes have been answering yes for longer than they’ve admitted. The question doesn’t require action. It requires honesty. And honesty about where you are is necessary before you can think clearly about where you might go.

What were you hoping the work would give you that it isn’t giving you now?

Energy. Meaning. The feeling of using the part of yourself that most wants to be used. A sense of growth. The specific satisfaction of doing something that feels like it’s yours.

Naming what’s missing is different from deciding to leave. It’s just naming what’s missing. That clarity is useful regardless of what you do next.

What are you still getting from this work that you’d have to deliberately replace?

This question matters because the answer is often more than just salary. Security, structure, identity, community, status, a sense of competence that’s hard to rebuild elsewhere.

These are real things. Acknowledging them isn’t a reason to stay in something that no longer fits. It’s a reason to be honest about the full picture when you’re deciding what to do with it.


What you’re not being asked to do

This isn’t a call to quit. It isn’t a suggestion that you’re in the wrong career. It isn’t advice.

It’s an invitation to look clearly at something that most professionals spend considerable energy not looking at.

You can be excellent at something and no longer be the person that work was built for. That’s not a failure of the work and it’s not a failure of you. It’s what happens when people grow and circumstances don’t always grow with them.

What you do with that knowledge is yours to decide. But you can only decide it honestly if you’ve first allowed yourself to see it clearly.


Is there something you’re very good at that you’d stop doing if you could? What would it take to name that honestly?

Before you go — one question: what’s the work you do well that quietly costs you? Reply to this email. I read everything and it shapes what I write next.

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