A few months ago I wrote about the freeze that can hit in the first year after selling a business, the sense that every decision feels both reversible and permanent at once. A handful of you wrote back to say it landed. I've since found the research that explains why. It isn't just me, and it isn't really about the money at all.
01 | Why founders regret selling
Research from the Exit Planning Institute and PwC puts the number at 75%: three out of four founders who sell say they regret it within twelve months. Not because the deal was bad. Because almost nobody prepares for what comes after.
Forbes recently told the story of a founder who sold her business for $12 million at 47 and still hit a wall. She'd planned for it, she thought: negotiated a consulting role to stay involved, expected the money to settle the underlying question, filled her calendar to avoid the empty space. None of the three worked. The question she was actually left holding was simpler and harder than any of that: who am I when I'm not fixing something?
That's not really a business problem. It's what happens when the thing that gave your days their shape disappears, whether that's a business, a job, or a career you'd quietly built an identity around.
02 | The retirement identity problem
A retirement psychologist recently wrote about a client, no debt, a strong portfolio, about as financially secure as it gets. And still isolated, obsessing over markets, quietly damaging his marriage by never talking about anything else.
The explanation on offer: people who build their identity entirely on professional achievement don't lose that need for achievement once the achievement disappears, they just redirect it, often straight onto the portfolio itself. Worth knowing: an 80-year Harvard study found relationship quality, not portfolio performance, is the strongest predictor of wellbeing in later life. Not the number. Who's actually around you.
03 | The picture nobody shows you
I wrote in an earlier issue about how not knowing your full financial picture is scarier than actually seeing it, however bad it turns out to be. There's a growing body of research on exactly this: financial avoidance and catastrophising are studied, common, mechanical responses to uncertainty, not a personal failing. Knowing that doesn't fix anything by itself. But it's a genuinely useful thing to know you're not the only one who does it.
If any of this landed, forward it to someone else standing at their own fulcrum point right now. That's still the best way this reaches the people who need it, better than anything I can do on my end.