Hi Reader

Too busy working to plan your way out of work

Had a meeting this week with a man I'll call Alan. Mid-fifties, very successful, owns a big house full of forty years of accumulated stuff, and a clear plan for retirement that involves selling that house, freeing up the money, sorting a few things out and stepping back.

And he's been sitting on that plan for ages, doing nothing about it. Not because he doesn't want to. Because he can't find the time.

He said it almost as a throwaway line, but it stopped me, because it's one of the truest things I've heard all year. He said, and I'm paraphrasing only slightly, "until I stop working, I won't have the time to organise all this. But while I'm still working, I haven't got the time."

Read that again. The thing standing between Alan and retirement is the time it would take to plan his retirement. And the only way to get that time is to retire. Which he can't do until he's done the planning. Which he hasn't got time for.

He's locked himself in a room, and the key is on the other side of the door.

The trap nobody warns you about

We talk a lot about whether people can afford to retire, whether they've got enough, and whether the numbers work. We talk far less about whether people have the bandwidth to actually execute the thing, and for a certain type of person, that's the real bottleneck, not the money.

Because retiring well isn't a single decision you make on a Friday. It's a project. There's the house to sort, the pensions to consolidate, the admin nobody enjoys, the conversations with family, the slow untangling of a working life from a personal one. It takes headspace. Real, unhurried, sit-down-and-think headspace.

And the people most likely to be financially ready to retire are very often the people with the least headspace to spare. The capable ones. The ones whose careers swelled to fill every available hour precisely because they're good at what they do and people keep handing them more. The better you are, the busier you are, the more the job demands, and the less room there is to plan your way out of it.

Alan isn't lazy. The opposite. He's so productive, so in-demand, so good at saying yes, that his own exit has become just one more item on a to-do list that never gets to the bottom. And it's the one item that, conveniently, has no deadline. Nobody's chasing him for it. The house will still be there next year. The plan can wait. Everything else is louder.

So it waits. And waits. And the years go.

Why the urgent always beats the important

There's an old idea that the urgent and the important are not the same thing, and that we spend our lives letting the urgent win.

Work is nothing but urgent. The email needs answering today. The client needs the thing by Thursday. The problem is on fire right now. Every bit of it arrives with a deadline attached and a person waiting on the other end, and so it gets done, because urgency is loud and specific and slightly stressful and impossible to ignore.

Planning your retirement is the opposite. It's important but never urgent. No one's waiting. There's no deadline. Nothing breaks if you don't do it this week. And so it loses, every single time, to whatever's on fire today. Not because it matters less. Because it shouts less.

The grim irony is that it's one of the most important projects of your entire life, deciding how you spend your remaining healthy years, and it's structurally designed to lose every fight for your attention, because it's patient and quiet and everything else is screaming.

You will never wake up to an inbox that says "URGENT: you are not getting any younger, please action your retirement today." That email doesn't come. The reminder that your healthy years are finite doesn't ping. So the thing that should be at the very top of the list sits quietly at the bottom, beaten daily by stuff that won't matter at all in five years.

You have to steal the time, because no one will give it to you

So what actually breaks the catch-22?

You have to treat planning your exit like it's the urgent thing, even though nothing about it feels urgent, because it's the only item on your list that's quietly deciding the shape of the rest of your life.

That means stealing time that the job will never willingly give you. Blocking out a day, a real one, not a leftover Sunday evening when you're knackered, and treating it like the most important client meeting in your calendar. Because it is. It's the meeting with the rest of your life.

It means accepting that the job will never make room for this. Ever. There is no quiet quarter coming where things finally calm down, and you'll get to it. That quarter is a myth. The work expands to fill whatever you give it, so the only way to get the time is to take it, ringfence it, defend it like you'd defend it for anyone else who mattered.

And it means being willing to say no to something urgent in favour of something important, which is the single hardest thing for this type of person to do, because saying yes is how they got here. But every yes to one more project is a no to the planning that gets you out, and at some point, the maths on that stops working in your favour.

Alan's problem isn't really time. He's got the same hours as everyone. His problem is that everything else has a voice, and his own freedom doesn't, so it keeps getting shouted down. The day he decides his exit is allowed to be loud too, allowed to bump something off the list, allowed to win a fight now and then, is the day the catch-22 quietly breaks.

The key's on the other side of the door. But it turns out the door was never locked. You just have to decide that walking over to open it matters more than answering the next email.

P.S. - If you've been "about to start planning" your retirement for longer than you'd care to admit, hit reply and tell me what keeps winning the fight for your time. I suspect there's a pattern in the answers, and I'd like to see if I'm right.