Two men, both now in their late seventies, said almost exactly the same thing to me within the space of a week. Simon, 72, told me: “I wish I’d stopped working at 58. I gave the best years of my freedom to a job that didn’t need me nearly as much as I thought.” The other, Dan, 73, said: “I wish I’d kept working past 65. I retired because it was expected, and I spent the next three years bored out of my mind wondering what I’d done.”
Same decision. Opposite regret.
After more than 40 years working as a psychologist with people approaching retirement, living through retirement, and sometimes struggling with what came next, I’ve become wary of anyone who claims there is one right way to retire. There isn’t.
But there are patterns in the regrets people share when they look back. What’s striking is that very few of them are about money. They’re usually about something else entirely.
Shorts
