Hi Reader

Alright, confession time.

I've spent the last three weeks essentially telling you that retirement is harder than anyone admits, your feelings are completely normal, and no amount of spreadsheet reassurance is going to fix the weird anxiety you've got about money.

Which is all true and important, but also... not exactly helpful on its own, is it?

So if you've been reading along thinking "Right, so I'm not broken, this is all normal, but what the hell do I actually do about it?" - this one's for you.

Because... the people who actually settle into retirement aren't doing what you'd expect.

THIS WEEKS SUBJECT IS...

WHAT I'VE NOTICED

Over the last few weeks, I've been writing about the stuff nobody mentions in the retirement brochures. The pressure that doesn't disappear, it just shape-shifts. The persistent unsettled feeling that makes you wonder if you've made a terrible mistake. The frustrating gap between knowing you're financially fine and actually feeling fine.

And the responses I've been getting? Bloody hell.

Inbox after inbox of people saying essentially the same thing: "Yes, this is exactly what I'm experiencing, I thought I was the only one, I thought something was wrong with me."

But here's what's started happening in the last week or so. People are moving past the relief of being seen and understood, and they're asking the obvious next question:

"Okay, so if this is all normal, if I'm not broken, if my financial planner can't fix this with better spreadsheets... then what actually does help?"

And I get it. Because I've spent three weeks essentially telling you that retirement is psychologically harder than anyone admits, that your feelings are valid, and that your brain is going to be weird about money regardless of how much you have.

Which is all true and important, but also potentially a bit... depressing? If I've just spent three newsletters explaining why you feel rubbish and then buggered off without offering anything useful, that's a bit of a wind-up, isn't it?

So here's what I've noticed about the people who actually do seem to settle into retirement - not perfectly, not without wobbles, but genuinely settle: they're not doing what you'd expect.

They're not the ones with the best financial plans (though that helps). They're not the ones who retired with the most money (though that doesn't hurt). And they're definitely not the ones who had it all figured out on day one.

The ones who seem to land on their feet? They've stopped trying to think their way into feeling better.

WHAT I THINK IS REALLY GOING ON

Here's what I reckon is happening: we've been sold this idea that retirement is a problem to solve. Get your finances sorted. Find some hobbies. Stay active. Maybe do some volunteering. Tick the boxes, follow the plan, and you'll be fine.

But what if retirement isn't a problem to solve? What if it's a transition to move through?

Because here's the thing about transitions - and I mean proper transitions, the big life ones like becoming a parent, losing a parent, moving countries, ending a marriage - they don't respond well to logic. You can't spreadsheet your way through grief. You can't productivity-hack your way through identity loss. You can't "five tips to feeling better" your way into accepting that your entire relationship with time, purpose, and self-worth has fundamentally changed.

And retirement? Retirement is one of the biggest identity transitions most of us will ever go through. You're not just leaving a job. You're leaving the entire structure that's told you who you are, what you're worth, and how to spend your days for the last four decades.

That's not a logistics problem. That's an existential one.

So when people ask me "what helps?" they're usually expecting me to say something like: make a schedule, join a club, take up watercolours, book that trip you've been putting off.

And sure, those things might help. But what I'm coming to realise more and more is that they're not actually the thing that helps.

Here's what I've seen actually make a difference:

First: Stop treating yourself like a problem that needs fixing. The unsettled feeling, the financial anxiety, the occasional "what have I done?" panic - none of that means you've made a mistake or that you're doing retirement wrong. It means you're human and you're going through a massive life change. The constant self-improvement project - trying to optimize yourself into feeling better - often just creates more pressure.

Second: Build tiny, boring practices that aren't about achieving anything. The people who settle in aren't the ones with the most impressive retirement plans. They're the ones who've built small, regular practices that ground them. A morning walk. Coffee in the same chair. Tuesday lunch with a mate. These aren't about productivity or self-improvement. They're about creating rhythm when the old rhythm is gone.

Third: Talk about the weird stuff. The loneliness. The identity wobble. The guilt about spending money. The days when you're bored out of your skull. The surprising grief. The marriage friction now that you're home all the time. Most people are white-knuckling it in silence, thinking they're the only one. They're not. Find one person you can be honest with about how strange this all feels.

Fourth: Give it more time than you think it needs. Everyone wants a timeline. "How long until I feel normal?" Honestly? For most people, it's somewhere between 18 months and three years before retirement stops feeling like something you're "adjusting to" and starts feeling like... just your life. That's not what anyone wants to hear, but it's what I've observed. And knowing that can actually help, because you stop panicking that something's wrong when month six still feels weird.

And finally: Let your relationship with money evolve. This one's the hardest. You've spent decades in accumulation mode. Learning to spend, to trust the numbers, to believe you have enough - that's not a switch you flip. It's more like... learning to trust your body after an injury. You have to practice, gently, repeatedly, in small ways. Start with something tiny. Give yourself permission to spend on one small thing this week without guilt. Not a big thing. The good coffee. The nicer seat on the train. The book you want instead of waiting for the library. Build the muscle slowly.

None of this is sexy. None of it will make a good LinkedIn post about "crushing retirement." But I've watched enough people go through this to know: the ones who do okay aren't the ones who had it all figured out. They're the ones who gave themselves permission to be a bit lost for a while, and built small practices to steady themselves while they figured out who they're becoming.

IF YOU WANT TO GO DEEPER

There's another piece to this puzzle that I haven't touched on here - and it's possibly the most important bit.

It's about why small problems suddenly feel enormous in retirement. Why a minor expense that wouldn't have registered during your working life now keeps you up at night. Why a cancelled plan or a rainy week can feel weirdly devastating.

I explore this in my recent video "The Redundant Brain Problem No One Talks About": [Link to your YouTube video]

​

AN EXERCISE TO TRY THIS WEEK

Right, enough sitting with questions. Let's do something practical.

I want you to map out what I call your "anchor points" - the small, regular things that ground you during the week. Not your big plans or achievements. The tiny, boring stuff that creates rhythm.

Get a piece of paper. Draw out a week - Monday through Sunday.

Now mark on it:

• Any regular practices you already have (morning coffee, evening walk, phone call with your sister on Wednesdays)
• Where the empty, unstructured time sits (be honest - where do the days feel shapeless?)
• One new tiny anchor point you could add (and I mean tiny: 15 minutes, same time, same place, once a week)

This isn't about filling every hour or being productive. It's about creating just enough structure to feel grounded without recreating the pressure of your working life.

Pick ONE new anchor point to try for the next four weeks. Not seven. One. Maybe it's:

• Tuesday morning walk to the bakery
• Thursday afternoon reading in the same chair
• Sunday evening call with a friend
• Friday coffee at the local café

Small. Regular. Not aspirational. Just something that creates a tiny bit of rhythm.

Try it for four weeks. Don't judge whether it's "working." Just notice what it feels like to have that one small point of structure in your week.

And if it helps? Add another one next month.

You're not building a new life overnight. You're building it one boring, small, regular practice at a time.

P.S. - If you try the anchor points exercise, I'd genuinely love to hear what you chose. Hit reply and let me know. Sometimes the best ideas come from hearing what's actually working for real people, not what the retirement books say we should be doing.