Hi Reader

You don't retire once

Two conversations this week, both with men who've "retired," and I use the quote marks deliberately, because between them, they've retired approximately four times and are all still working.

The first, I'll call him Ken. Ken has retired three times. The first time was about nine years ago. It lasted a month, then his clients rang and asked him to come back directly, so he did. The second time was six years ago. That one also lasted about a month, until a company offered him a "six-month project." He's still on that project more than five years later. He said to me, with a straight face and a bit of a laugh, "It's hard to pin me down." He's not wrong.

The second, call him Greg, retired two months ago. He sat there and told me, honestly, that he can't stop taking calls from headhunters. Somebody rings with an interesting gig and a big number attached, and he hears himself going "well, yeah, go on then, I'll have a conversation." Three months in, and he's taking interviews for jobs he doesn't need and says he doesn't want. His actual reason for booking a meeting with me? In his words, to "give me permission."

Two very different men, in the exact same situation. They both thought retirement was a thing you do once. It isn't, and nobody warns you about that.

Retirement isn't an event. It's a decision you keep having to make.

Here's a narrative that I think we're all sold. Retirement is a door. You work right up to it, you have a party, you walk through, and it shuts behind you. One decision, made once, done. You are now Retired, capital R, and that's that.

For a certain kind of person, that's a complete fantasy.

Because the salary stops, yes. But the offers don't. The phone doesn't magically stop ringing the day you hand your badge in. If anything, it rings more, because the moment the word gets out that you're free, every former client, every old contact, every headhunter with your number thinks the same thing, ah, he's available now.

So what actually happens is this. You don't make one big decision to retire, you make a hundred small ones, over and over, for years. Every time someone dangles an interesting project in front of you, that's a decision. Every time a recruiter calls with a stupid number attached, that's a decision. Every "we really need someone exactly like you for just six months," that's a decision. Retirement isn't the door slamming once. It's standing in a doorway that never fully closes, with people politely asking if you fancy stepping back in, roughly once a fortnight, for the rest of your life.

Ken didn't fail to retire three times because he's weak. He failed because each time, a specific, flattering, well-paid offer landed in front of him, and saying yes was the easiest thing in the world. Nobody plans to still be working five years into a six-month project. You just say yes to one more reasonable-sounding thing, and then another, and the years quietly stack up.

Why "yes" is the path of least resistance

The reason this catches people out is that every individual yes is completely defensible.

Of course Ken went back when his clients asked, they needed him, it was only meant to be a bit of work. Of course Greg's taking the interview, it's a fascinating company and the money's absurd, and it's just a chat, where's the harm? No single yes looks like a mistake. Each one, on its own, is a perfectly sensible thing to agree to.

But that's exactly the trap. The decision to keep working never arrives as one big obvious choice you can weigh up properly. It arrives disguised as a series of small, flattering, easy-to-justify yeses, each one so reasonable that turning it down would feel almost rude. Saying yes is frictionless, someone else has done the asking, the path is right there, all you have to do is not resist. Saying no takes effort, and it normally means disappointing someone. It means choosing an empty Tuesday over a definite, validating, well-paid thing to do.

So yes wins. Not because you decided your retirement should involve five more years of work, but because you never actually got to make that decision. It got made for you, one flattering phone call at a time.

The goal was never to stop. It's to make it a real choice.

Now I want to be really clear with you, because it would be easy to read this as "stop saying yes, you fool." That's not it at all.

There is nothing wrong with Ken doing work he enjoys. He mentors students, he's energised by it, he lights up talking about it. There's nothing wrong with Greg fancying an interesting project. The problem was never the work itself.

The problem is that neither of them is actually choosing it, they're just failing to resist it. And those are completely different things, even though from the outside they look identical.

Failing to resist is what Greg's doing right now, hearing himself say "go on then" to interviews on autopilot, pulled along by the flattery and the momentum and the sheer ease of yes. Choosing is what happens when you know, deep in your bones, that you don't need the money and you don't need the validation, and from that position of total freedom, you look at the offer and decide, genuinely, whether you actually want it.

Same yes, but utterly different meaning. One is a reflex. The other is a free choice.

And this is the whole point of getting your financial house in order, it was never about being able to stop working. It's about reaching the position where work becomes optional. Where the next phone call isn't a temptation you have to white-knuckle your way past, but simply an offer you can weigh on its own merits, take it or leave it, no pull, no pressure, no autopilot. That's what Greg was really asking me for when he said he wanted permission. He didn't want permission to stop, he wanted to know he was free enough that saying yes or no was entirely, cleanly his.

The question

So if you're recently retired, or heading that way, here's the thing I want you to understand.

The offers are going to keep coming. The phone will keep ringing. That's not a sign you've done retirement wrong, it's just what happens when capable people step back, the world keeps asking for them. You don't get to make one clean decision and be done. You'll be making it again and again, every time something shiny lands in your inbox.

So the question isn't "how do I stop working?" It's "am I choosing this, or just failing to resist it." When the next call comes, and it will, are you saying yes because you genuinely want that thing, from a place of complete freedom? Or are you saying yes because it's flattering and it's easy and it's right there, and saying no feels like hard work?

Because you don't retire once. You retire every time the phone rings, and you decide, freely this time, whether to pick it up.

P.S. - If you've "retired" more times than you'd care to admit, hit reply and tell me how many. I'm collecting them, and Ken's three is the record so far. I suspect some of you can beat it.