Midlife MavericksI spent an entire day last week in meetings in London.
Back-to-back.
Man after man after man.
Smart. Senior. Accomplished.
And just as we were packing up lunch, coats on, it happened.
You know the moment.
The just before you go moment.
He hesitated. Shifted his weight.
Then said:
“Look… just before you go… I just want to ask you something.”
With men, it always comes at the very end.
In passing.
Like an afterthought they’ve been carrying for years.
He was 44. Maybe 45. Senior. Well-paid. Respected.
And he said, quietly:
“What can I actually do?”
Then, almost apologetically:
“I mean… what skills do I really have?”
“If I don’t want to do this anymore… and money isn’t the issue… what’s left?”
“I don’t think I have any real skills.”
That sentence hit the room like a dropped glass.
Because I hear that sentence all the time.
Just usually from women.
Quote of the Week
“Doubt is not a sign of weakness. It’s a sign of transition.”
Adam Grant
The CEO Job He Didn’t Want
An hour later, I had another conversation that keeps looping in my head.
This one was with a man who had done everything “right.”
COO of one of the largest tech companies in Europe.
At 49, he was offered the job.
CEO.
Major UK company.
Serious money. Prestige. Visibility. Influence.
The full package.
He had everything people chase their entire careers for.
And he said, almost surprised by his own clarity:
“I realised I just didn’t want it.”
Not fear. Not burnout.
Just… no desire to go back into an office.
No appetite for the structure.
No pull toward the identity anymore.
Then the realisation landed:
“If I don’t want this job… I don’t think I want any job ever again.”
He’d graduated.
When “Unemployable” Becomes Your Superpower
I laugh about it now, but it’s true: I’ve made myself unemployable.
Not because I can’t get a job.
But because my identity is no longer compatible with employment.
Not the politics. Not the hours. The compression.
The idea of one role, one boss, one definition of value, one way of working.
Once you’ve tasted autonomy, flow, and choice? Going back doesn’t feel aspirational anymore. It feels small.
The problem? Context collapse.
When the environment that validated you disappears, or stops fitting, doubt rushes in to fill the gap.
For many men, identity has been welded to role, status, income, responsibility.
So long as the machine is running, promotions coming, money flowing, the questions stay quiet.
But when the desire shifts from more to enough?
The floor drops out.
At a certain level, employment stops being safety and starts being risk.
Risk to energy, curiosity, time, identity.
The Question That Actually Matters
The people who get stuck ask: “What skills do I have?”
The ones who move forward ask: “What problems do people already trust me to solve, without a job title?”
Skills are abstract. Problems are concrete.
Your career already translates. Job title becomes outcome. Tasks become leverage. Experience becomes value.
Portfolio Careers
A modern portfolio career isn’t retired men on committees or non-exec roles as a slow fade-out or “keeping busy.”
It’s multiple income streams driven by interest, leverage, and choice.
Some for money. Some for learning. Some for contribution. Some for pure curiosity.
Not about easing out. About expanding sideways.
Your identity stops being tied to one title, one employer, one lane.
And once that decoupling happens? Going back feels impossible.
Own It
What struck me last week wasn’t that men have imposter syndrome too.
It was how long they wait to admit it.
By the time they ask the question, they’re not looking for confidence.
They’re looking for permission to stop playing a game they’ve already won.
If you’re reading this and thinking “I don’t want another job” or “I don’t want one thing anymore” or “I want freedom, variety, flow, and leverage” – you’re ready for a different structure. One that fits who you’ve become.
Hit reply. Tell me where you are. I’ll tell you what I see.
I’ll be here with my third espresso, reading every response.
