In June 1986, Andrew Ridgeley walked away from one of the most successful pop acts in the world.
Wham! had sold over 30 million records. Six UK number ones. Sellout tours. A concert in China — the first Western pop group to play there. They were at the height of their fame, not the end of it. Nobody was forcing the decision.
Ridgeley made it anyway.
Years later he was asked about the split. He corrected the interviewer. It wasn't a split, he said. They brought Wham! to a close in a manner of their own choosing. He knew George's future lay outside the band. He knew his own future did too. So they finished it properly — a farewell concert at Wembley Stadium in front of 72,000 people — and walked away on their own terms.
Ridgeley moved to Cornwall. Quiet life. Out of the spotlight.
George Michael stayed in the game. More albums, more tours, more headlines — the brilliant and troubled solo career of one of the greatest voices of his generation.
George Michael died on Christmas Day 2016. He was 53.
I'm not drawing a simple moral from that. George Michael's life was his own and the reasons for how it ended are complex and not mine to reduce to a business lesson.
What I am saying is this.
One of them knew when. He made the decision himself, while the choice was still his to make, and built a life on the other side of it. The other stayed in the game until the game ended it for him.
The question this newsletter exists to ask is a simple one.
Will you know when?
Most entrepreneurs I know have a vague idea of when they want to exit.
Fifty-five. Sixty. When it feels right.
What they don't have is a plan for recognising the moment when it actually arrives. And that gap — between the intention and the ability to act on it clearly, at the right time, for the right reasons — is where a lot of very good exits go wrong.
The moment doesn't announce itself. It doesn't arrive with a fanfare or a sign that says *this is it, you're done, you can go now.* It arrives quietly — in a broker call you nearly didn't answer, in a morning when the answer to a question you've been asking yourself for years is finally different from what it's always been.
And if you haven't done the work to recognise it, you'll miss it. Or worse — you'll feel it and talk yourself out of it, because there's always one more year that would make the business worth a little more, one more thing to fix before it goes to market, one more reason why now isn't quite right.
I know this from my own experience.
The broker called while I was isolating in bed with Covid, two weeks before our wedding. I nearly didn't answer. Something made me pick up — and I've thought about what that something was many times since. It wasn't desperation. It wasn't exhaustion. It was readiness. A quiet, settled sense that we were close enough to our number to make the conversation worth having. For the first time in thirteen years of building, I could hear the question “have you considered selling?” without the automatic internal response that said “not yet, not now, too much still to do.”
