Hi Reader

You want to know exactly how much money you'll need, down to the pound if possible.

You want to know what you'll do with your time, ideally mapped out by day and activity.

You want to know where you'll live, whether you'll downsize or stay put or move to the coast.

You want to know how you'll feel - happy, fulfilled, purposeful - and you want guarantees that it'll all work out the way you're planning.

And I get it, I really do, you're about to make one of the biggest decisions of your life, and uncertainty is uncomfortable, so you're doing what any sensible person would do - you're trying to eliminate it, replace it with certainty, create a plan so detailed and well-researched that nothing can possibly go wrong.

There's just one problem... retirement is inherently uncertain, possibly one of the most uncertain things you'll ever do, and pretending you can plan your way to certainty might actually be setting you up for a harder landing than if you'd just admitted you don't know what you're getting into.

THIS WEEKS SUBJECT IS...

WHAT I'VE NOTICED

I spend a lot of time in meetings with people who are 6 months, 12 months, maybe 18 months from retirement, and there's this pattern I see over and over.

They want answers, specific answers, definitive answers - "Will £800,000 be enough?" "Should I take the 25% lump sum?" "Is Spain better than Portugal for retiring?" "How much can I spend per year?"

And look, some of those questions have actual answers, we can run the numbers, do the projections, look at the data, that's the relatively easy bit.

But then they ask the questions that don't have answers: "Will I be happy?" "Will I get bored?" "Will my marriage survive us both being home all day?" "Will I regret leaving?"

And what they want - what they're really asking for - is for me to give them certainty about things that are completely uncertain, they want me to say "Yes, you'll be fine, yes you'll be happy, yes this is the right decision" with enough conviction that they can stop worrying about it.

But I can't do that, nobody can, because I don't know who they'll be in six months, I don't know what will matter to them when work isn't there anymore, I don't know if they'll love having free time or if it'll drive them mad, I don't know if the things that sound appealing now will still be appealing when they're actually doing them.

One guy I met with a few months back had built this incredibly detailed financial model - different scenarios, different spending levels, different market conditions, stress tests, the works, and it was genuinely impressive, he'd thought of everything.

But then he said something that stuck with me: "If I can just get the numbers right, if I can just nail down all the variables, then I'll know I'm making the right decision."

And I'm thinking, mate, the numbers are the easy bit, it's not the variables in the spreadsheet you need to worry about, it's the variables in your head and your life and your marriage and your sense of purpose that you can't possibly model.

Another woman, about a year from retirement, kept asking me variations of the same question: "But what do people actually do all day?" Like if she could just understand the exact mechanics of how retired people fill their time, she could replicate it and everything would be fine.

And I get why she's asking, she's trying to make the uncertain certain, trying to find a formula that works so she doesn't have to sit with not knowing, but the uncomfortable truth is that what people do all day varies wildly and what works for someone else probably won't work for her and she won't know what works until she's actually in it.

WHAT I THINK IS REALLY GOING ON

Right so here's what I reckon is happening.

Our brains hate uncertainty, like properly hate it, uncertainty feels dangerous because for most of human history uncertainty meant actual physical danger - is that rustling in the bushes a predator, is this food safe to eat, is that person a threat - so we evolved to crave certainty, to feel safer when we know what's coming, when we can predict and plan and control.

And for most of your working life, you could create reasonable certainty - you knew what you'd be doing tomorrow, you knew roughly what next year looked like, you had salary projections and career paths and retirement dates, the future was knowable within certain parameters.

Then you get close to retirement and suddenly you're facing this massive uncertain thing - you don't know who you'll be, you don't know what you'll want, you don't know how you'll feel, you don't know if you'll be happy or bored or fulfilled or lost - and your brain absolutely hates this, it wants certainty, it needs certainty to feel safe.

So you do what you've always done when faced with uncertainty: you try to plan it away, you gather more information, you build more detailed models, you research and analyse and strategise, because surely if you just think hard enough and plan thoroughly enough, you can make this uncertain thing certain.

But here's the problem - and this is the uncomfortable bit - retirement isn't actually plannable in the way you're trying to plan it.

You can plan the financial side, sure, you can run the numbers and stress test your pension and figure out safe withdrawal rates, that's just maths and probabilities, that bit is actually knowable.

But you can't plan who you'll be, you can't plan what will feel meaningful to you when work isn't there anymore, you can't plan how you'll react to having unstructured time, you can't plan whether you'll love it or hate it or feel somewhere weirdly in between, you can't plan your way through an identity transition.

And trying to creates this dangerous comfort, dangerous because it's false, you feel like you've got it sorted because you've got a plan and you've done the research and you know what you're going to do, but actually you've just created an illusion of certainty about something that's inherently uncertain, and when reality doesn't match your plan - which it won't, it never does - you're going to feel like you've failed rather than understanding that the plan was always just your brain's attempt to manage anxiety about the unknown.

The people who handle retirement best aren't the ones with the most detailed plans or the most research or the most certainty about what they're doing, they're the ones who are genuinely comfortable saying, "I don't know yet, and that's okay."

They've made peace with uncertainty, they've accepted that they won't know what retirement feels like until they're in it, they've built financial safety nets and done enough planning to feel secure, but they've also left massive space for not knowing, for discovering, for changing their minds, for being wrong about what they thought they'd want.

They're planning for uncertainty rather than planning to eliminate it, and that's a completely different approach.

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 trying to nail down every variable:

Not the surface stuff like "how much money I'll need" but deeper - are you trying to guarantee you won't regret this decision, are you trying to prove to yourself you've got it all figured out, are you trying to feel safe, are you trying to avoid the discomfort of not knowing who you'll be?

And here's the follow-up: what if you can't make those things certain, what if they're fundamentally unknowable until you're actually living them?

Because here's what I've noticed - the more you try to create certainty about the inherently uncertain parts of retirement, the more rigid your expectations become, and the harder it is when reality inevitably deviates from your plan.

But if you can get comfortable with uncertainty, if you can genuinely embrace "I don't know what I'll want in six months and that's okay," if you can plan for flexibility rather than planning for certainty, you're actually setting yourself up for a much easier transition.

The certainty you're craving - the guarantee that you'll be happy, that you've made the right decision, that it'll all work out - nobody can give you that, not your financial planner, not the retirement books, not the people who've already done it.

The only certainty is that it'll be uncertain, that you'll have to figure it out as you go, that who you are now won't be who you are a year from now, and that's not a problem to solve, that's just... retirement.

So maybe the question isn't "how do I make this certain?" but "how do I get comfortable with it being uncertain?"

Because the comfort of certainty might feel safer right now, but it's a dangerous comfort if it stops you from being flexible enough to handle what actually happens rather than what you planned to happen.

P.S. - If you're close to retirement and struggling with the uncertainty of it all, hit reply and tell me what you're most uncertain about. Sometimes, just naming it helps, and honestly, I'm curious what we're all trying to make certain that probably can't be.