Ep 110 - The Permission Paradox

You've got the money. You've got the time. You've got the freedom. So why can't you actually enjoy it?

In this episode, I unpack the Permission Paradox! The reason financially secure retirees still order the cheap coffee, skip the trip, and quietly guard a fortune they'll never spend. It's not a money problem. It's a permission problem. And it's fixable.

FULL SHOW NOTES

Open your banking app. Look at the number. Now answer honestly: when did that number last get smaller because you actually enjoyed yourself?

Not the boiler. Not the tax bill. Not inflation. You — on purpose — spending money on something that made your life better.

If you can't think of a date, you don't have a money problem. You have a permission problem.

That's where this episode starts. And it goes somewhere you probably didn't expect.

What I cover:

The Trap — For forty years, your spending had structural alibis. The bonus paid for the holiday. The salary justified the car. The job title covered the nice restaurant. Retirement vaporises every one of those vouchers, and suddenly there's no external authority signing off on anything. Just you, your money, and a question you've never really had to answer before: Am I allowed?

Why You're Like This (Not Your Fault, Still Your Problem) — Three reasons. Four hundred years of Protestant work ethic quietly teaching you that unspent money is virtue performed in public. Four decades of training the saving muscle and ignoring the spending one. And the uncomfortable truth that a lot of high-net-worth retirees don't actually believe they deserve it. Imposter syndrome doesn't retire when you do. It just changes its uniform.

What's In The Vault — The fears keeping you from spending are almost always fog. "The future." "Care costs." "Inflation." "Something I haven't thought of." When you press on the fog with real numbers, it usually dissolves. You're not protecting against ruin. You're protecting against a story you inherited from people who genuinely did have to worry about the workhouse. You are not your grandfather. You are a millionaire, pretending to be a peasant. And the cost of that pretence is the entire second half of your life.

The Good News — The permission problem is a skill problem. Not a personality problem. Not a values problem. A skill. And skills can be learned. Dan shares what it looks like when people finally flip — and what the three permissions actually are that make it happen.

The Three Permissions — Permission to enjoy what you've built. Permission to spend the window (that active, healthy retirement window is twelve to fifteen years — not thirty). And permission to become someone new.

CHALLENGE OF THE WEEK

Do one thing this week that feels slightly uncomfortable. Order the proper coffee. Book the flight you've been talking about for two years. Pay for something for one of your kids without making a thing of it. Take a Wednesday afternoon off, from nothing. Buy the silly shoes.

Whatever it is — do it once. Notice the sky doesn't fall. Then do it again next week.

That's how the muscle gets built. One flat white at a time.

KEY QUOTE

"You are a millionaire, pretending to be a peasant. And the cost of the pretence is the entire second half of your life."

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This podcast is for educational and informational purposes only. It does not constitute regulated financial advice or a personal recommendation. Dan Haylett is a financial planner regulated by the FCA, but views expressed are his own.