The Right Time to Retire Isn’t Always the Optimal Time

I retired at 58 years young. I feel there’s always been tension in the retirement world around when to actually pull the trigger. The common argument goes like this: your late fifties mark the peak earning decade of your career, so retiring early is basically sabotaging your future self. It’s a valid point, and the numbers usually back it up.

But here’s what I think: while the maths matters—and for some people makes early retirement impossible or genuinely foolish—for others, including me, it was absolutely the right call. Life has a habit of getting in the way of optimization, whether you realize it in the moment or only through hindsight.

Take my own circumstances. I was pretty frazzled and burnt out from running my own business for nearly thirty years. The thought of keeping going was not appealing in the slightest, and the thought of working for someone else was totally unpalatable after having full agency over my working life for such a long period. An opportunity to sell presented itself and I took the plunge into retirement. In the moment, it was the right choice for me.

But then there’s hindsight.

I’ve only been retired nine months, but my wife’s degenerative disc disease has taken a real turn for the worse. I help her get shoes and socks on now. Sometimes getting out of a chair is impossible without help. We can still travel, still go walking, still work in our garden together—still jump on a plane before cramped seats become too much hassle and not worth the back pain. But in five or ten years? That might become difficult or impossible in ways we can’t yet imagine.

And then there’s my youngest daughter, in her mid twenties, she had thyroid cancer that we thought was beaten. It came back a few months ago, and has now invaded the local bone tissue in her neck. Targeted radiotherapy and radioactive iodine treatment are in the very near future. I’m glad I’m 100% available for that.

Don’t get me wrong—the financial opportunity cost is real. Those peak earning years everyone talks about happen to be real. But what’s also real is being able to drop everything for a medical appointment, to spend a Tuesday afternoon in the garden because my wife’s back is feeling good, to be mentally present instead of perpetually distracted by work. Money I can budget around. Time I can’t get back.

Foresight would have been wonderful, but hindsight has shown me something a nicely presented spreadsheet never could: I made the right choice in the moment. Maybe take this tale as a reminder that we often work to “secure the future,” but we sometimes forget that the future eventually arrives—and it rarely looks like the pristine, trouble-free version we imagined. Life happens, keep that in mind during your retirement planning.