Hi Reader

No one's coming to tell you to stop

Two meetings this week, two men, both comfortably able to retire, and neither of them doing it. And by the end of the second conversation, I realised they were stuck on exactly the same thing, just wearing different disguises.

The first, I'll call him Roy, is in his mid-sixties, runs his own consultancy, and has just landed a project he's genuinely excited about after years of work that bored him senseless. His wife, I'll call her Sandra, retired a few years back after three decades in the NHS, and she said something that stuck with me. She retired, in her words, with no guilt whatsoever. Done her time, body and spirit said enough, walked out, never looked back.

Roy can't do that. And he knows he can't, which is half the problem.

The second man, call him Tony, is in tech, financially sorted, and told me, completely deadpan, that he's got "a little stupid flag in the ground" at 70. No reason. Just a number he's decided he's working to. He also mentioned a colleague who retired and then, in Tony's words, "pleaded to come back two days a week because he couldn't stand it." He told me that story as a warning. I think he meant it as a warning about retiring. I heard it as a warning about something else entirely.

There are two ways to leave, and only one of them is easy

Here's a thing I've come to believe after a lot of these conversations. There are basically two types of people heading into this stage of life, and they have wildly different experiences of it.

The first type gets worn out. The nurses, the builders, the teachers, the people whose job grinds on the body or the soul until one day it hands them a clean, obvious finish line. Sandra's one of those. The work itself tells you when you're done. You don't have to decide, you just have to listen, and the deciding is made for you. It's not painless, but it's clear.

The second type never gets that. The knowledge workers, the consultants, the advisers, the people whose entire value lives in their head. And here's the cruel little joke of it. Their bodies don't wear out at the same pace, and their value doesn't drop, it climbs. They hit their early sixties knowing more than they've ever known, more useful than they've ever been, right at the peak of the thing they're good at.

Nobody's coming to tell that person to stop. There's no finish line being handed over. The work doesn't get worse, it often gets better. So the off-switch that Sandra got just never arrives, and they're left having to do the one thing that's genuinely hard, decide, with no help, to walk away from something they're brilliant at and still enjoy.

Most of them don't. They just keep going and quietly tell themselves it isn't a choice.

The stories we tell to avoid the decision

And this is the bit that gives the whole thing away.

Roy describes what he does as a hobby. "I'm a hobbyist," he said, more than once. And Sandra, who has known him for forty years and has no patience for nonsense, just looked at him and said, "No. You're still bloody working." Which was the truest thing said in the whole meeting.

Because that's what we do. We don't admit "I'm choosing to keep working because I can't yet face who I'd be without it." That's too raw, too exposing. So instead, we reach for a story that turns the choice into a circumstance. It's just a hobby. I'm only keeping my hand in. I'm needed on this one. I've got a flag at 70. The client can't manage without me. The money's a bit tight this quarter, so I'd best keep going.

They all sound reasonable. They're all, mostly, cover stories. They let you keep doing the thing without ever having to look squarely at the fact that you're doing it because the alternative scares you.

Tony's flag at 70 isn't a plan. It's a way of not deciding. And his colleague, who begged to come back two days a week, wasn't weak, he just discovered he'd built his entire sense of being useful out of a job, and when the job went, there was nothing underneath it. That's not a warning about retiring. That's a warning about never building anything other than work to stand on.

The work isn't the problem. The pretending is.

Now, I want to be clear, because this is easy to get wrong. I'm not telling Roy to give up the project he loves. God no. Work that genuinely lights you up in your sixties is one of the great privileges of this stage, and the idea that you must stop just because you've hit some age is its own kind of stupidity.

The problem was never the work. The problem is the pretending.

It's the difference between "I'm doing this because I love it and I've looked honestly at everything else and I still choose it" and "I'm doing this because it's the only thing holding the shape of my life together and I'd rather not examine that too closely." From the outside, they look identical. Same desk, same hours, same emails. Inside, they're completely different. One is freedom. The other is hiding.

And the only way to tell which one you're in is to be honest about whether you could stop. Not whether you want to, whether you could. If the honest answer is "I genuinely don't know who I'd be," then the work isn't a choice you're making, it's a place you're sheltering, and the hobby story is the tarpaulin you've thrown over it.

So here's the thing I'd leave you with, if you're one of the ones for whom the finish line never showed up. No one is coming to tell you to stop. Your body probably won't do it, your clients certainly won't, and your own brain will happily supply you with reasonable-sounding stories until you're 80. The finish line, if you want one, is one you're going to have to draw yourself.

The people who do this well don't quit the work they love. They just stop pretending they have no choice in it. And it turns out that once you know, really know, that you're choosing it freely, you do a lot less of the stuff you were only ever doing to hide.

P.S. - If you've caught yourself telling one of these stories, the hobby, the flag, the one last project, hit reply and tell me which one. I collect them at this point, and I'd genuinely love to know what yours is, and whether you think it's a free choice or a place you're sheltering.