20 Years In, 20 to Go: The Question Every Mid-Career Leader Needs to Ask

By Sandra Collomb, Founder of SANOPAZ

There's a moment that happens to a lot of senior leaders around the 15 to 20 year mark.

You've built something. A career, a reputation, a track record. You've led teams, delivered results, navigated crises. By every external measure, you're doing well.

And yet.

Something feels off. Not broken, not catastrophic. Just, quietly, off. Like a hum in the background you can't quite locate. You find yourself in a meeting, doing the thing you've done a hundred times, and a small voice asks: is this still it for me?

Why this happens at this stage

Mid-career for most senior leaders isn't what it looks like from the outside. From the outside it looks like confidence, authority, arrival. From the inside it often feels like a growing gap between the life you've built and the life you actually want.

Part of this is developmental. The first twenty years of a career are largely about proving yourself, building skills, earning trust, getting to the next level. There's a clear game to play and you've been playing it well.

But somewhere around the halfway point, the game changes. The external markers of success stop feeling like enough. The promotion you worked towards arrives and the satisfaction lasts about three weeks. The title, the salary, the seat at the table, all real, all hard-won, all somehow not quite the point anymore.

This isn't ingratitude. It's growth. It's your inner life catching up to your outer life and asking for a seat at the table too.

The question most leaders avoid

I work with a lot of leaders at this exact moment. And the question I ask, that usually stops them mid-sentence, is this:

If you could design the next twenty years of your working life, what would actually matter to you?

Not what looks good. Not what makes sense on paper. Not what your company needs or your family expects or your industry respects. What matters to you.

Most high-achieving leaders haven't asked themselves this question in years. They've been executing, delivering, leading. They've been so busy being good at the game they forgot to check whether it's still the right game.

The ones who pause and answer honestly, those are the conversations that change things.

What gets in the way

The mid-career reckoning is uncomfortable for a few reasons.

First, there's the identity question. If you've spent twenty years becoming a particular kind of leader in a particular kind of role, asking "is this still what I want?" can feel like pulling a thread that unravels everything. It doesn't. But it feels that way.

Second, there's the guilt. You have a good life. People would love to have your problems. Who are you to feel restless? This is one of the most common things I hear, especially from leaders who are genuinely good humans. The guilt keeps them silent about the question, which keeps them stuck.

Third, there's the fear that asking the question means you have to blow everything up. It rarely does. Most of the leaders I work with don't leave their organisations or reinvent their careers entirely. They recalibrate. They reconnect to what matters. They make space for the parts of themselves that have been quietly waiting.

What it looks like to actually move through it

The leaders I've seen navigate this well share a few things in common.

They get honest. Not performatively honest, really honest, about what's energising them and what's draining them. About where they feel alive in their work and where they're just going through the motions.

They reconnect to their values. Not the values on the wall, their actual values. The things that, when they're honoured, make them feel like themselves. And when they're compromised, make them feel hollow.

They allow themselves to want things. This sounds simple. It isn't. Many senior leaders have become so practised at managing others' needs that they've lost touch with their own. Giving yourself permission to want something different, to grow in a new direction, to lead in a different way, that's an act of courage at this stage.

And they find someone to think with. Not to be told what to do. But to have a space where the question can be asked out loud, without judgement, without consequence, without having to perform certainty they don't feel.

The real opportunity

Twenty years in is not a crisis. It's an invitation.

An invitation to lead the second half of your career with more intention than the first. To stop optimising for the wrong metrics. To build something that is not only successful, but meaningful. To become the kind of leader that people remember, not because of what you delivered, but because of who you were while you delivered it.

The question isn't whether you've done enough. You have.

The question is: what do you actually want to do with what you've built?

That's worth sitting with. And if you'd like to explore it with someone who has sat with it themselves, I'd love to talk.

Book a free 20-minute Strategy Discovery Call, no pitch, no pressure. Just a real conversation about where you are and where you want to go.

Sandra Collomb is the founder of SANOPAZ, a boutique executive coaching and advisory practice. She works with senior leaders navigating complexity, transition, and the question of what comes next.