Hi Reader

You've got a plan for retirement, haven't you?

Maybe it's in a notebook, maybe it's a spreadsheet, maybe it's just been living in your head for the last eighteen months, but it's there, it's detailed, it's colour-coded possibly, and it maps out exactly what your retirement is going to look like.

Monday mornings you'll go to the gym, Tuesday afternoons there's that Italian class you've been meaning to take for years, Wednesdays you'll volunteer somewhere meaningful, Thursdays are for reading all those books you never had time for, Friday you'll finally sort out the garden properly, weekends are for seeing friends and maybe some local exploring.

It's a good plan, a solid plan, the kind of plan that makes you feel like you've got this whole retirement thing figured out, like you know exactly who you're going to be when you stop being who you are now.

There's just one small problem, and I'm sorry to have to tell you this... you're absolutely not going to follow it.

Not because you're lazy or undisciplined, but because you're planning for a person who doesn't exist yet, and when they do exist they're probably going to want completely different things than you think they will.

THIS WEEKS SUBJECT IS...

WHAT I'VE NOTICED

I’ve seen this pattern so many times over the last few years it’s basically become its own category.

Someone’s six months out from retirement, maybe a year, and they’ve built this incredibly detailed vision of what their days are going to look like. They’ve researched courses and clubs and volunteering opportunities, they’ve mapped out their week like they’re creating a timetable for a particularly well‑organised school term.

One guy I met recently, retiring in about eight months, showed me his plan. It was in a spreadsheet, broken down by day and time slot, colour‑coded by category (personal development, physical health, social connection, creative pursuits). He’d even built in buffer time for “spontaneous activities”.

And I’m looking at this thing thinking, mate, you’re not going to do any of this, are you?

Not because it’s a bad plan, it’s actually quite a sensible one, it’s just… it’s a plan for someone you’ve invented, not someone you actually are.

I recently spoke with a woman, about a year from retirement. She told me she’d already signed up for three different courses starting the month after she finishes work: watercolour painting, Spanish lessons, and a creative writing workshop. On top of that, she’d committed to volunteering two days a week at a local charity.

“I want to hit the ground running,” she said. “I don’t want to be one of those people who just drifts.”

And I get it, I do. The plan feels like control, like you’re taking charge of this massive life transition instead of just letting it happen to you.

But here’s what I’ve noticed... the more detailed the plan, the less likely any of it actually happens.

Because what you’re really doing when you build these elaborate retirement schedules isn’t planning, it’s identity construction. You’re trying to create a version of yourself that feels acceptable, respectable, proof that you won’t just become one of those retired people who potter about in their slippers watching daytime telly.

Which is fine, except you’re building this identity before you’ve even left the old one. And the person you are now, still working, still busy, still defined by your job, has completely different ideas about what sounds appealing than the person you’ll be six months into retirement.

WHAT I THINK IS REALLY GOING ON

Right, so here’s what I reckon is actually happening.

When you’re close to retirement, properly close, can see the finish line, counting down the months, you start getting anxious about who you’re going to be when you stop being who you are now. Your work identity is about to disappear and you need something to replace it with, something that proves you’re still a valuable person with purpose and direction.

So you build a detailed plan, because the plan itself becomes a kind of identity: “I’m the person who’s going to learn Italian and get fit and volunteer and read all the classics.” It’s an identity you can claim right now, before you’ve even retired. It makes you feel sorted, purposeful, like you’ve got your act together.

The problem is that this plan is based on who you think you should be in retirement, not who you’ll actually want to be.

It’s based on the retirement brochure version... active, engaged, constantly learning, growing, and contributing, because that’s the version our culture approves of, the version that proves you’re not just giving up or becoming irrelevant.

Nobody makes a detailed plan that says, “Mondays I’ll probably stay in my pyjamas until noon; Tuesdays I might go to the garden centre just to have somewhere to go; Wednesdays I’ll feel a bit lost and maybe watch four episodes of something on Netflix; Thursdays I’ll wonder what the point of any of this is,” because that doesn’t sound like a plan, it sounds like failure.

But honestly, that’s probably closer to what the first six months will look like for most people.

Retirement isn’t just a change of schedule; it’s a complete identity shift. You’re not the same person you were when you were working. Your energy is different, your sense of time is different, and what feels meaningful or worth doing is different... and you won’t know what any of that actually feels like until you’re in it.

The people I see who settle into retirement well aren’t the ones who follow their detailed plan. They’re the ones who make a plan, ignore it, feel a bit guilty about that for a while, then gradually work out what they actually want to do rather than what they thought they should do.

The plan still serves a purpose. It gets them through the anxiety of the transition and gives them something concrete to focus on instead of just sitting with the uncertainty of becoming someone new. But the real value isn’t in following it; it’s in having something to let go of once they realise it isn’t really them.

And here’s the uncomfortable bit: you probably know this already, don’t you? Somewhere in the back of your mind, you know that Italian class sounds good in theory, but you’re probably not going to drag yourself there every Tuesday afternoon when you could just be sat in the garden with a coffee. You know the gym three mornings a week sounds very healthy and disciplined, but past experience suggests you’re not really a three-mornings-a-week gym person.

You’re making the plan anyway because, right now while you’re still working, you need to believe in that version of yourself: the productive, purposeful, engaged version. The alternative, not knowing who you’ll be or what you’ll want, feels too uncertain and a bit scary.

So you plan for the person you think you should become, knowing full well you probably won’t become that person. And that’s okay. It’s part of the process of letting go of one identity before you’ve figured out the next one.

A QUESTION TO SIT WITH

Here's what I want you to think about this week, especially if you're close to retirement and you've been building one of these detailed plans in your head or on paper:

Not what activities are in it, but what's the plan itself doing for you right now? Is it making you feel in control, is it proving to yourself (or others) that you won't just become boring and irrelevant, is it filling the anxiety gap of not knowing who you'll be, is it your way of performing "I've got this sorted" when actually you're not sure you have?

And when you look at what would happen if you didn't have a plan, I don't mean forever! Just for the first few months, what if you just... saw what happened, noticed what you actually wanted to do rather than what you think you should do, gave yourself permission to be a bit lost and unstructured while you figure out who this new version of you actually is.

Because here's the thing... the detailed plan might be protecting you from something important, the uncertainty and discomfort of not knowing who you'll be, and that uncertainty is actually where the real work happens, that's where you discover who you're becoming rather than who you think you should become.

Your plan is probably beautiful and well-thought-out and full of good intentions, and you're almost certainly not going to follow it, and that's completely fine, maybe even necessary.

Maybe the point isn't to follow the plan, maybe the point is to make the plan, feel safe for a bit, then let it go when you realise the person you're becoming doesn't need it anymore.

P.S. - If you're close to retirement and you've made one of these detailed plans, I'd genuinely love to hear what's in it, hit reply and tell me, no judgment, I'm just curious what we all think we're going to become.