There’s a story I keep hearing.
Different person, different pension pot, different postcode — but the same story.
Someone sits across from me, either in my office or on a Teams meeting, retirement either imminent or already arrived. They’ve done everything right. They’ve saved diligently, invested wisely, sacrificed the fancy holidays and the flash cars while colleagues splashed cash they didn’t have. They’ve built something genuinely impressive.
And now they can’t touch it.
Not because they can’t. Because something won’t let them.
The Man Who Couldn’t Buy the Jacket
Let me tell you about a client — I’ll call him David, though his name doesn’t matter because you probably know a dozen Davids.
David retired at 63 with a pension pot that would make most people weep with relief. Not obscene money. But more than enough. Cashflow modelling showed he could spend £7,000 a month, comfortably, until he was 95, even after stress-testing for bad markets, inflation, and the kind of longevity that would make Methuselah nervous.
In our meeting his wife told me about a recent shopping trip. He saw a jacket that he really liked. He picked up the jacket. Admired the jacket. Looked at the price tag. £249.
He put it back.
His wife looked at him. “I thought you liked it?”
He shrugged. “I’m not paying that much for it. Anyway, I don’t need another jacket.”
“David, you have over a million pounds in your pension, buy the bl**dy jacket.”
“Nah, I’m ok.”
That’s not frugality. That’s a prison — and David built it, one responsible financial decision at a time.
But here’s what I’ve come to understand about David, and the hundreds of people just like him.
He didn’t build that prison alone. It was partly built for him. Decades ago. By people who loved him and were doing their very best. But people who were experiencing a different life than David does now.
Before We Talk About Money, We Need to Talk About Childhood
When I became a Specialist in the Psychology of Financial Planning, I took a course with a financial psychologist named Dr Brad Klontz. He’s spent much of his career studying something most financial advisers never think to ask about: where did your relationship with money actually begin? From these studies, he invented the phrase ‘money scripts’.
“Money scripts — typically unconscious, trans-generational beliefs about money — are developed in childhood and drive adult financial behaviour.” — Dr Brad Klontz
Read that again. Trans-generational. Passed down through families. Like eye colour, only more damaging and considerably harder to spot.
Think about that for a moment.
The reason David put the jacket back has very little to do with David. It has everything to do with what David witnessed, overheard, absorbed, and inherited about money before he was old enough to question any of it.
Maybe his parents struggled, like most people did a generation or two ago. Maybe money was spoken about in hushed, anxious tones. Maybe he watched his father stress about bills or heard “we can’t afford that” so often it became his inner monologue.
Maybe he was told to ‘eat all his dinner because he doesn’t know where the next meal is coming from’.
Maybe he heard that ‘money doesn’t grow on trees’ multiple times.
Maybe there was a financial crisis — a redundancy, a business failure, a period of genuine hardship — that left a mark so deep it became a permanent feature of how his family viewed the world.
“Money scripts are usually developed in response to emotionally charged events related to personal and family finances. They are formed in childhood and last through adulthood unless identified and challenged.” — Klontz et al.
The key word there is emotionally charged. We don’t remember the lessons we were taught in neutral, abstract terms. We remember the fear in our mother’s voice. The tension at the dinner table. The look our parents exchanged when a bill arrived. Those moments write the script. And then, for the next fifty years, we perform it — without ever reading what’s written.
The Superpower That Became a Cage
Here’s the uncomfortable irony.
The very belief that made David successful — that money must be guarded, preserved, never squandered — is the same belief now preventing him from enjoying the fruits of that success.
Klontz identifies four money scripts that shape our financial behaviour: Money Avoidance, Money Worship, Money Status, and Money Vigilance. David falls into that last category.
“Money Vigilance is the most financially healthy script — it includes a tendency to be alert, careful, and frugal with money. But taken to an extreme, it can lead to anxiety or an inability to enjoy financial success.” — Klontz
Money Vigilance got David here. It absolutely got him here. The higher net worth, the disciplined saving, the avoided debt — all of it flows from a vigilance script that rewarded caution at every turn.
But retirement doesn’t reward vigilance in the same way. Retirement asks something the Money Vigilant script has never been programmed to do: stand down.
The funny thing is you think that, once you retire, you’ll do all those things. No, you won’t. This is something you have to practise.
You cannot simply decide, on the day you stop working, to become a different person with a different relationship with money. The script doesn’t work like that. It’s been running for forty plus years. It’s not going to switch off because you handed in your work laptop.
What You’re Really Dealing With Is Not a Money Problem
When a client like David struggles to spend in retirement, I used to instinctively regurgitate the cash flow charts and the spreadsheets. I would show him the numbers. I would demonstrate — clearly, logically, irrefutably — that he can afford the jacket, the holiday, the kitchen extension, the business class flight to see his daughter in Sydney.
And he nods. He understands the numbers.
Then he puts the jacket back.
“Our disordered relationships with money aren’t our fault. They don’t stem from a lack of knowledge or a failure of will. Instead, they are a product of subconscious beliefs and thought patterns, rooted in our childhoods, that are so deeply ingrained in us, they shape the way we deal with money our entire adult lives.” — Klontz & Klontz, Mind Over Money
For thirty or forty years, David was emotionally rewarded — by his bank balance, his sense of self-worth, his identity — for doing the exact opposite of what retirement now requires.
Every tenner he tucked away was another brick in his wall of security. Another umbrella for the rainy day.
He delayed gratification. He controlled his spending. He preserved capital. He avoided mistakes. He accumulated.
And then I walk in and say: “Right, now do the opposite”. Is it any wonder that feels psychologically terrifying?
Reversing the Operating System
Think of it like this.
For four decades, David’s brain has been running a programme. The Accumulator. Every time he saved instead of spent, the programme got a reward signal. Every time he resisted temptation, it reinforced itself. Over thousands of repetitions, it became his identity.
Retirement doesn’t just ask him to change a habit. It asks him to uninstall the operating system.
And you cannot do that with a spreadsheet or a cash flow chart.
The first step — the one most financial advisers skip entirely — is simply helping clients see the script. Not judge it. Not feel ashamed of it. Just recognise it.
“I notice you’re uncomfortable spending. Where do you think that comes from? What was money like in your house growing up?”
That conversation alone, in my experience, is worth more than any amount of portfolio rebalancing.
Because once David understands that the anxiety he feels reaching for his wallet isn’t rational — it’s ancestral — he can start to question it. And questioning it is where everything begins to change.
Seven Ways I Try To Help Someone Emotionally Access Their Own Money
1. Give Permission Through Evidence — Repeatedly
Cashflow planning, done right, isn’t just financial modelling. It’s psychological therapy.
Not: “You’re fine.”
But: “Look. Here’s what happens if you spend £5,000 more a year. Here’s what happens in a crash. Here’s what inflation does. Here’s what happens if you live to 98.”
I try to show them surviving every scenario. Show them still having money. Show them it’s okay. Then show them again next year. And the year after.
Because the goal isn’t mathematical certainty. It’s emotional certainty. And emotional certainty takes repetition — because you’re not just updating a spreadsheet. You’re slowly, patiently, rewriting a script that’s been running since childhood.
2. Start With Controlled Experiments
You don’t ask a man who’s been fasting for forty years to sit down to a banquet. You start small.
“This month, increase your discretionary spending by £500. Book a nicer hotel on your next holiday. Upgrade your flight. Take the family out. Outsource the stuff you hate doing.”
Then, a few months later, you ask not “how’s the money?” but “how did that feel?”
Almost universally, the answer is: nothing bad happened. The world didn’t end. The wealth is still there. And quietly, imperceptibly, the anxiety starts to loosen its grip.
The Money Vigilance script was written through lived experience — it can only be rewritten through lived experience. Give it safe experiences to learn from.
3. Separate “Security Money” From “Freedom Money”
This one is powerful.
In our industry we have a term called ‘capacity for loss’. Technically, it’s the figure that people can lose in £s and % terms from a stock market crash before it will affect their future spending and lifestyle plans.
This is the glass half empty outlook.
But there is also a glass half full outlook for capacity for loss.
Because I use cautious assumptions in my cashflows, I feel quite comfortable telling my ‘too much money’ clients that their capacity for loss figure can also represent their surplus. Their bucket list money.
For example, if a client has £1.5 million invested but his cash flow shows that that £1.2 million, prudently invested, will fund his core lifestyle indefinitely. Then the £300,000 is surplus.
He can throw it away, go on some great holidays, buy his dream car…hey, maybe even buy a £249 jacket.
Your Capacity for Loss is not just your security. That’s your adventure fund. Money whose only job is to enhance your life.
Without this distinction, every pound spent feels like chipping away at the safety net. That’s the Money Vigilance script at full volume — every pound spent is a threat.
With it, there’s a pot of money that carries no emotional weight. Money that exists to be used. That changes everything.
4. Ask the Uncomfortable Question
Gently. Thoughtfully. Not as a challenge — as a genuine question.
“What is the purpose of this money now?”
Or, for the braver moments:
“If you die with significantly more than you needed, while unnecessarily restricting your life in the meantime… was the plan successful?”
I’ve seen that question create breakthroughs no spreadsheet ever could. Because most people haven’t thought it through. The script told them to accumulate — it never told them why, or when to stop.
5. Detach the you from your situation
I’ve done this countless times, and the concept works in an instant. Getting it to stick still takes time however!
I sit down with a client. Pull up a cashflow. And tell them I need their opinion on a case I’m working on. I show them the numbers. The assets. The projected unspent wealth. The looming inheritance tax bill their family will face.
Then I ask: “What advice would you give this client?”
They answer immediately. No hesitation. No anxiety. No script running in the background.
One man — mid-seventies, £2.5 million invested, the kind of Money Vigilant who only ever wanted to talk about his portfolio performance vs the benchmark — looked at the numbers I’d put in front of him and said without blinking: “Tell him to start spending his money.”
I let that sit for a second.
Then I told him it was his own plan.
The silence that followed said more than any cashflow ever could.
Here’s what this tactic does. We are all capable of perfect clarity when the emotions aren’t ours. We can see exactly what someone else should do. We can see the waste, the unnecessary restriction, the absurdity of hoarding money you’ll never spend while the years quietly disappear.
And it’s always easier to give other people advice than to take it ourselves. Not because we’re foolish. But because our own money comes loaded with everything we’ve ever felt about it — every anxious conversation we overheard, every sacrifice we made, every year we went without so that one day we wouldn’t have to.
Strip that away — even for sixty seconds — and the answer is obvious.
The job, sometimes, is just getting out of your own way so you can see things more clearly.
6. Spend On Values, Not Stuff
When working with a ‘money vigilant’ client the goal is never to turn a disciplined saver into a reckless spender. Most lifelong savers recoil at the idea of waste — and they’re right to.
But those same people will spend freely — even joyfully — on experiences, family, health, time, convenience, legacy, and generosity.
The reframe isn’t “spend more.” It’s “use money intentionally.” That feels morally acceptable to the Money Vigilant brain — because the script was never really about money. It was about security, love, and not letting people down.
Spending on family? That’s love. On health? Security. On time? Wisdom. Find the values. The spending follows.
7. Introduce the Decumulation Mindset
For forty years, the question was: How much can I build?
Retirement asks a fundamentally different question: How well can this support my life?
That’s not a small shift. For someone whose identity is built around the Money Vigilance script, it can feel like being asked to redefine who they are. Because in a very real sense, that’s exactly what it is.
Most advisers can tell you whether someone can retire. Very few can help someone emotionally enjoy retirement without fear.
That gap — between financial readiness and emotional readiness — is where the most meaningful work happens.
The Real Job Description
I’ve come to believe that the most important thing a retirement planner does has nothing to do with investment strategy or tax efficiency.
It’s helping someone see the script they’ve been running — often since they were eight years old, sitting at a kitchen table, listening to their parents worry — and gently, patiently, helping them write a new one.
One that says: you did it. You can enjoy it now. That’s not weakness. That’s the whole point.
It may take months (often 2- 5 years) of patient work, repeated cashflow reviews, a few carefully placed questions – and conversations about what money was like in his house that he will never forget.
But if that’s what it takes to help clients to finally give themselves permission to stop performing a script that was written for a different time, a different world, and a version of themselves that no longer needs protecting – then it’s worth it.
That’s the job.
Now go buy the jacket.
