What I got wrong about career progression
What I got wrong about career progression
For a long time, I thought I knew what progress looked like.
More responsibility. Bigger teams. Broader scope.
Each step up felt like movement in the right direction. Like things were going as they should.
At one point, I was leading around 80 people.
And I don’t regret any of that. There’s a lot I learned from it. A lot I’m proud of.
But if I’m honest, I don’t think I ever really stopped to question why I was chasing it.
What I thought it meant
I think I associated progression with scale.
More people meant more impact. A bigger role meant I was doing something right. It was visible. It was measurable in a way that felt clear.
It also looked how a career is supposed to look.
You move up. You take on more. You lead more people. You become more responsible for bigger things.
That narrative is everywhere.
And it’s easy to follow it without really questioning whether it fits.
What changes at that level
The reality of those roles is different.
You move further away from the work. Your time is spent in conversations, decisions, alignment, managing the shape of things.
That work matters. It’s important.
But it’s also more abstract.
You’re not as close to the problems. You’re not as close to the building. There’s more distance between thinking and doing.
And over time, I think I lost something in that.
What I didn’t realise at the time
I don’t think I realised how much I valued being closer to the work.
Being able to explore ideas directly. To build things. To test, change, move quickly.
To feel the impact of decisions in a more immediate way.
Those things become harder at scale.
Not impossible. But harder.
And I think I only really noticed that once I stepped back from it.
What’s changed now
More recently, I’ve been working in a much smaller team.
Six or seven people.
Closer to the work. Less distance. More direct involvement in what we’re actually building.
And I’ve enjoyed it more than anything I’ve done in a long time.
Not because it’s easier.
But because it feels more real.
More connected. More tangible. Less about managing from a distance and more about actually doing.
Rethinking what progress means
It’s made me rethink what progression actually is.
For a long time, I thought it was about moving up.
Now I’m not so sure.
Sometimes it’s about moving closer.
Closer to the work. Closer to the problems. Closer to the things that actually give you energy.
That doesn’t make one path better than the other.
But it does make it more obvious that there isn’t a single direction everyone should be moving in.
Closing
I don’t think I got it wrong.
But I do think I followed a version of success that I hadn’t properly questioned.
And now that I have, things feel a bit clearer.
Not in terms of what comes next.
But in terms of what actually matters to me, and I’m having the time of my life.