I seem to hear the same phrase several times a week these days.
Sometimes it’s at an event. Sometimes it’s over lunch. Sometimes it’s from a former colleague I haven’t seen for a while. Occasionally it’s from somebody who has somehow managed to steer a conversation about music, sport, holidays or the weather back round to their pension arrangements.
The phrase itself varies slightly, but the meaning is always the same.
“Of course I could retire tomorrow.”
I’ve reached the point where I barely react to it. Not because it’s unusual, but because it’s become so predictable. Partly that’s an age thing, of course. When you’re in your twenties, people talk about promotions, mortgages and where they’re going on holiday. Once you reach your fifties and sixties, conversations start drifting towards pension pots, downsizing, buy-to-lets, grandchildren and whether Portugal is really as good as everyone says it is.
What I find interesting, though, is that the people who tell me they could retire almost never seem to be making any serious effort to do so. In fact, the opposite is often true. The man explaining that he no longer needs to work is also advising three startups, chairing a board, mentoring two founders and somehow fitting in enough lunches to keep half the hospitality industry afloat. The woman telling me she could walk away tomorrow is in the middle of writing a book, raising money for a charity and planning a new business venture. Neither looks remotely ready for a life of daytime television and discounted coach trips.
Which makes me wonder whether retirement is actually the point.
There’s a particular version of this I notice mostly, though not exclusively, among men in their early fifties. It isn’t really about freedom at all. It’s a flex dressed up as a throwaway remark, a way of saying look how well I’ve done without having to say it outright. The pension pot becomes the new company car. I can usually tell the difference within about thirty seconds of a conversation starting, and it’s a different thing entirely from what follows.
Because for most people, I don’t think it’s boasting about money, at least not consciously. What they’re really talking about is freedom. They’ve reached a stage where they no longer have to do certain things. They can choose their projects. They can choose who they work with. They can say no to the client, the boss, the commute or the endless internal meeting that should have been an email.
That’s a wonderful position to be in. But it isn’t retirement. It’s autonomy. And the two are very different things.
Over the past year, through The Third Half, I’ve talked to musicians, academics, founders, campaigners, former executives, sportspeople and charity leaders. Many of them are well beyond the stage of life where anyone would blame them for putting their feet up, yet very few seem interested in doing so. What drives them isn’t money, and in most cases it probably hasn’t been money for years. It’s curiosity, contribution, the chance to build something or support something or leave something behind. Some are writing albums. Some are launching businesses. Some are mentoring younger people or campaigning for causes they care about. A few are doing all of it at once. The common thread is that they remain engaged with the world around them.
I suspect that’s what a lot of people actually mean when they tell me they could retire tomorrow. What they’re really saying is that they’ve earned the right to choose.
Fair enough.
But there’s another group. You know the ones. The people who have been telling you they could retire for the last five years. Every conversation somehow circles back to it. Every lunch includes an update. Every social gathering brings a fresh analysis of whether next year might finally be the year. At some point it starts to sound less like a plan and more like a hobby, and that’s the bit I struggle with.
Retirement isn’t a hostage negotiation. It isn’t a software implementation project. It doesn’t need quarterly updates and a steering committee. If you want to retire, retire. Travel, volunteer, read, walk, golf, paint, grow tomatoes, learn Italian, spend more time with your family, whatever it is that makes you happy, go and do it.
But if you’ve been telling me every six months for the past decade that you could retire tomorrow, I reserve the right to conclude that you don’t actually want to. And that’s fine too. Just be honest about it. There’s nothing wrong with continuing to work, create, contribute and stay involved if that’s what gives you energy. Some of the happiest people I know have built exactly that life.
So here’s my entirely unsolicited advice.
If you want to retire, FFS just do it!!
The rest of us don’t need the quarterly update.



You’re right it’s about choice rather than I could but I don’t. Freed from financial pressures you can focus on what you want not what you have to do… Torastan, mentoring, pleasant lunches and the like ❤️😬
But why would you want to if you are having fun?