Hi Reader

Most people I work with are financially secure but emotionally uncertain. The gap between the numbers and our feelings about them fascinates me, and if you want to live the second half of your life with joy, happiness, and peace of mind, it's worth exploring this together.

THIS WEEKS SUBJECT IS...

WHAT I'VE NOTICED

Let me tell you about a conversation I had last Tuesday. And last Thursday. And literally three times this week already.

Someone sits down with me - let's call him Sam, because one of them actually was named Sam - and we go through their retirement numbers. We pull up the spreadsheets. We run the projections. We look at their spending, their savings, their state pensions, their private pensions. We stress-test the whole thing: market crashes, inflation spikes, living to 105, unexpected health costs, the lot.

The numbers don't just whisper "you're fine." They shout it, very loud, with a megaphone. They could spend 30% more and still be absolutely, completely, mathematically fine.

I point to the big screen to show him the graphs. He looks at them, nods slowly and says "That's... that's really good to see,".

There's a pause.

Sam: "But what if the market..."

Me: "We already accounted for that."

Sam: "Right, but what about..."

Me: "That too."

Sam: "Okay, but honestly, do you think I should really be spending money on that trip to Portugal, or should I just..."

Sam and his wife, according to every rational measure available to modern financial planning, could go to Portugal, Italy, AND take a Mediterranean cruise and still die with more money than they started retirement with.

But Sam's nervous system didn't get the memo.

I used to think this was just about needing better charts, clearer explanations, more data. Like if I could just present the information the right way, the anxiety would lift.

I was wrong, because the anxiety doesn't live in the spreadsheet. It lives somewhere much older and much louder than that.

WHAT I THINK IS REALLY GOING ON

Your brain is kind of a paranoid disaster when it comes to retirement money, and it has exactly zero interest in your Monte Carlo simulations.

For forty-some years of your adult life, you operated on a simple, comforting principle: "I can always make more money if I need to." Got an unexpected expense? Do some overtime. Need a bigger cushion? Ask for a payrise, switch jobs, do some extra work. Your earning power was like this invisible safety net beneath everything you did.

Even when money was tight, there was an underlying assumption of 'The money can keep coming in. I have agency here'.

Then you retire, and that engine shuts off.

Sure, you've got your savings. Maybe a pension. The state pension. But that primal part of your brain - the part that kept your ancestors alive by being paranoid about food stores running out - isn't doing maths. It's doing threat assessment, and it's registering one very clear signal:

NO MORE INCOMING.

This is a big deal, and we don't talk about it enough.

It doesn't matter if you have a million quid in the bank. It doesn't matter if the safe withdrawal rate says you're sound for the next thirty years. Your nervous system looks at a finite pool of money and thinks: "We're eating through our reserves. This is bad. Red alert. Stop all non-essential spending immediately."

It's not logical, but it is deeply human.

And here's where it gets more complicated: many of today's retirees are carrying around some serious financial baggage. Maybe you grew up with parents who lived through the war, and stories about rationing and "making do" were just part of the furniture. Maybe you lived through the chaos of the '70s and '80s, or watched your pension pot get hammered in 2008 right when you were supposed to be home free. Maybe you've just spent so many decades being careful, being responsible, being the person who saves instead of spends, that the idea of actually using your money feels like betraying who you are.

Those experiences don't evaporate just because someone with a calculator tells you it's okay to spend £150 on a nice meal out.

We've created this incredibly sophisticated system for determining financial security - algorithms, probability models, risk assessments - but we've barely scratched the surface of how to help people feel financially secure.

Because feeling secure isn't about having more information. It's about building a completely new relationship with money when the old rules no longer apply. It's about grieving the loss of your earning identity (yes, grieving - that's not too dramatic). It's about learning to trust that spending money in retirement isn't reckless - it's literally the point. And it's about giving yourself permission to enjoy what you've spent decades building.

The maths can tell you you're fine, but your body needs to believe it. And that takes time, practice, and a different kind of work than most financial planning accounts for.

IF YOU WANT TO GO DEEPER

My latest video is called ‘Retirement Anxiety Is Real—Here's What's Actually Causing It’

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A QUESTION WORTH SITTING WITH

Here's what I want you to do this week. Find a quiet moment - actually quiet, not half-scrolling-your-phone quiet - and ask yourself this:

Not "what would I buy?" That's too easy. I mean... How would you breathe differently? What decisions would you make differently? What would you give yourself permission to do or enjoy? What worry would you finally set down?

Maybe you'd stop checking your account balance every other day. Maybe you'd book that trip without the guilt. Maybe you'd order the good wine instead of the house pour, just once, just to see what it feels like. Maybe you'd spend less time doing worst-case-scenario maths in your head and more time actually living the life you saved for.

Sit with this question. Write about it if that helps. Talk about it with your partner. Let it be uncomfortable if it needs to be.

Because the gap between "knowing you're fine" and "feeling fine" is where a lot of people spend their entire retirement. And that seems like a terrible waste, doesn't it?