You Haven't Failed. You've Succeeded at the Wrong Things.

There's a particular kind of person I work with who doesn't fit the usual narrative about midlife struggle.

They haven't lost everything. They haven't had a dramatic breakdown. They haven't been fired or divorced or left by someone they loved.

In fact, from the outside, their life looks almost enviable.

Good income. Respected career. A family they love. A home they worked hard for. Some financial security. The kind of CV that makes people at dinner parties ask impressed questions.

And yet.

There's something they can't quite name that sits underneath all of it. A low-grade restlessness. A sense that the engine is still running but nobody's sure where the car is going. A quiet question that keeps surfacing in the shower, on Sunday evenings, in the gap between meetings: is this it?

These are the people I find hardest to explain to anyone who hasn't felt it themselves — and the people I'm most equipped to help.

The problem with succeeding at the wrong things

When I burned out in 2008, I was a director at one of the world's largest companies. I had everything that was supposed to matter. Status, salary, trajectory. People reported to me. I had a corner office in the metaphorical sense.

And I was completely, quietly miserable.

Not in a dramatic way. Not in a way that made me easy to help or easy to read. The misery was subtle — the kind that hides behind busyness, behind another goal to chase, behind the reasonable voice that says "you should be grateful, look at what you have".

What I eventually understood — not quickly, and not without help — is that I had been working with extraordinary discipline toward goals I'd inherited rather than chosen. I'd been succeeding. Just at the wrong things.

This is the hidden problem in midlife for high achievers.

The skills that make you successful in your 30s — the focus, the drive, the ability to push through discomfort toward a distant goal — become a liability in your 40s and 50s if nobody ever asks you to stop and check whether the goal is still the right one.

Most people don't stop. Because stopping feels like failure. Because the momentum of a successful life is hard to interrupt. Because the people around you are congratulating you, not questioning you.

So you keep succeeding. At the wrong things. And the restlessness gets louder.

What this actually looks like

I've coached enough people at this crossroads to recognise the patterns.

It looks like the entrepreneur who sold their business and felt — instead of relief — a strange flatness they couldn't explain to anyone, including their spouse.

It looks like the corporate director who hit their long-held salary target and found themselves thinking, and now what?, in a way that frightened them.

It looks like the professional who relocated to Portugal for the life they'd always wanted and discovered, six months in, that the life they'd always wanted didn't feel the way they'd imagined.

It looks like the person who has money — real money, not just enough — and still can't answer the question: what am I actually doing this for?

None of these people failed. They succeeded. The problem is that success, pursued long enough in the wrong direction, brings you somewhere you didn't mean to go.

The shift that changes everything

What I've found — in my own life and in the lives of the people I work with — is that this moment, uncomfortable as it is, is not a problem to manage. It's information.

The restlessness is not a malfunction. It's a signal.

It means that some part of you knows the current direction isn't right, even if the conscious mind hasn't caught up yet. It means you have enough — enough experience, enough self-knowledge, enough accumulated wisdom — to want something more than just more of the same.

The question isn't what's wrong with me?

The question is: what is this trying to tell me?

That's where real midlife coaching begins. Not with a five-step plan or a morning routine or a vision board. With an honest, unhurried conversation about what you've built, what you actually want, and the gap between the two.

What comes next

The people I work with aren't broken. They're at a crossroads — which is a completely different thing.

A crossroads means there's a choice to make. It means the road ahead is not yet fixed. It means the next twenty years can look genuinely different from the last twenty, if you're willing to stop, look honestly at where you are, and make some deliberate decisions about where you're going.

That's the work I do with clients — across Wealth, Purpose, and Health, as one integrated life. Because the question of what to do with your money and the question of what gives your life meaning and the question of how to stay vital and energised into the second half — these aren't separate conversations. They're the same conversation, looked at from different angles.

If you read this and something in it felt familiar — if the restlessness is there, even quietly — I'd encourage you not to push it back down.

It's worth a conversation.

Asaf Hacmon is a certified midlife coach based in Lagos, Algarve, working with successful professionals and entrepreneurs in their 40s and 50s on Wealth, Purpose, and Health.

He holds a law degree, an advanced MBA, and spent fifteen years in corporate leadership and entrepreneurship before founding Blue Sky Coaching. He has personally navigated burnout, a near-death illness, business sale, and family relocation across Europe.

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Contact me

+351 926 915 570
asaf@blueskycoach.me

My practice

Rua das Maias 18,
Portelas (Algarve)
South Portugal