'When I hit the number, I'll know.'
Most of you at this stage have a number. Some of you will have it written down, but most just carry it around.
It's the figure that says you can stop, or finally do the thing you've been putting off for ten years.
I've noticed something about it.
It moves.
You get close, and it drifts. A bad year in the markets, perhaps, or another round of school fees. So you run the figures again.
Earlier this year, a man of 55 posted on a retirement forum.
'I have run my financials 1000's of times (OCD!) and I'm good.'
He'd done the sums. They said yes.
Then came his next line.
'Not sure what I'm retiring "to".'
I'd say that second line is what the number has been standing in for. Money is part of it, of course. Underneath, more often than not, sits a question of permission.
Researchers at Harvard Business School surveyed more than 4,000 millionaires across 17 countries. They asked the ones who weren't already at ten out of ten for happiness how much more wealth it would take to get them there.
The most common answers ranged from double what they had to ten times more.
What struck me was that it barely mattered how much they already had. Even among those worth $10 million or more, the most common answer was still twice as much.
To be fair to the money, the wealthiest people in the study were a little happier. Other research finds that for most of us, wellbeing keeps rising with income. So I'm not going to tell you money doesn't matter. It does.
What the study shows is how the finish line tends to move with you, whatever you're worth.
Try imagining it for a moment. The number lands tomorrow. The money's there, and every spreadsheet you've created agrees.
What do you do on Monday morning?
If the answer comes quickly, the number may be all that's in the way. If your mind goes blank, the way it seems to have for the man on the forum, that blank deserves more of your attention than the next spreadsheet.
When I sold my business I had a number in mind that I would finish with, post earn-out. During that 3-year period, though, I ended up feeling so trapped that I was willing to forgo the earn-out (a significant 6-figure sum) if it meant that I could be free. The advice I received, and share freely now, is to be happy with what you receive on day 1.
While having all the money in the bank was life-changing, I felt enormous fear that it wouldn't be enough for the rest of my life. Particularly as I was pivoting into what could potentially be low-income work as a psychotherapist.
That fear had me chase numbers again and pivot to more lucrative work. I couldn't completely accept or settle into having enough.
Here's another way of looking at it.
Plan the money properly, ideally with a good financial planner, and know your numbers. That part is just sensible.
Then notice what you've been asking the number to do for you.
Most of the men I've coached have wanted it to give them some kind of permission. To slow down, perhaps, or to want something different from the life they've built.
The number can't give you that. It was never designed to.
One small thing for this week. Finish the sentence below. Best write it down if you can, rather than in your head.
'When I hit the number, I'll finally...'
Whatever comes after 'finally', ask yourself whether it needs the number at all. Some of it will. I'd guess a surprising amount won't.
What's one thing on that list you could start before the number arrives?
More to Play For lands every Tuesday, one idea at a time, for successful men at midlife who've built the career and want the next decade to count. If this one spoke to you, subscribe below and the next one will come straight to you.
Matt
Sources: Donnelly, Zheng, Haisley and Norton, 'The amount and source of millionaires' wealth (moderately) predicts their happiness', Personality and Social Psychology Bulletin (2018) · Killingsworth, Kahneman and Mellers, 'Income and emotional well-being: a conflict resolved', PNAS (2023) · a post on the Early-Retirement.org forum (February 2026)