I didn’t retire to take it easy. I quit the career I was so passionate about to do it all on my own, at last. I’d built a reputation, lifted others up, and accumulated, not enough for yachts and champagne, but enough for safety and freedom. With my days and my adventures to spend, and content that, at long last, I see what money and happiness in retirement are actually about.
This time last year, I had the most amazing pottery weekend away. I crafted one shapeless bowl, drank the worst cup of coffee with strangers, laughed so hard my ribs hurt. That £200 and those two days taught me more about how to live well than any spreadsheet ever could.
This experience raised my awareness of something pretty common among retiring people: No matter how prepared we are for the money, the emotional transition, catches us off guard.
The Paradox of the High-Achieving Retiree
You’re not the typical retiree. You didn’t slide through a job that just counted pension days.” You created something that mattered, a business, an expertise, and a reputation. You walked away because you had the right to do so.
But freedom is both a gift and a trap.
Studies indicate that people like us experience a retirement identity crisis three times more often than the general population. We are shaped by our thoughts, actions, and willingness to help. Without those, who are we?
You are too smart for shallow hobbies, too awake for clichés. Playing golf and gardening seem like an insult to your brain. But floating in empty days? That feels even worse.
The Creativity Trap: When Your Best Asset Betrays You
Our analytical nature can sometimes work against us. I’ve noticed this in some of my friends and myself, especially as we get older:
Smart people overthink things too much. A weekend escape becomes 15 beautifully designed spreadsheet tabs comparing the weather, flights, hotel pillows, and activities. A pottery class becomes a self-examination: Am I any good? What if I quit halfway?
Wharton’s Adam Grant discovered that top performers spend an awful long time a month on decisions others make in moments. In retirement, you can easily allow every day to become a series of micro-decisions.
I needed to know that, too: Money buys choices, but happiness lies in the messy, slightly ragged edges you don’t plan to death.
The £50,000 Prize: Changing the Game in Retirement and Life
Most retirement advice assumes you’re either struggling wholly or financially wealthy. Many of us are neither here nor there; we live in between, comfortable enough for reasonable choices, but still mindful of budgets.
Take James, a friend and a retired architect, mortgage-free with a healthy pension. For years, he’s fantasized about a £2,000 woodworking course.
“But what if I hate it?” he says. “That’s a month’s budget down the drain.”
I told him what I told myself: What if you end up loving it? What if that small risk buys you years of laughter, sawdust, and a reason to leap out of bed every morning? How much is it worth never to know?
You are permitted: You don’t need to request consent from anyone.
Retirement also taught me that you never have to explain your ‘yes’.
That art history class you failed when you were 18 and never recovered from? Take it now. Not for a diploma, Monet still quickens your pulse.
That brilliant idea you’re constantly researching. Write the first bad chapter; no one is judging.
The hiking boots by the door? Put them on. The hills will wait. Your knees might not.
The £20 Rule: My Shortcut for More Yes
And the rule that changed everything:
If it’s an experience that costs less than £20 an hour, I’ll say yes.
· £80 to learn to make pasta? Yes.
· £ 150 for a day’s drawing class? Absolutely.
· £300 for a weekend pottery retreat? A thousand times, yes.
No overthinking. No price comparison. No spreadsheets. Just living.
Little “yeses” can add up to real money and happiness in retirement.
Find Your Social Network Again
Your network is not just old colleagues, it’s your next adventure club.
That coworker who was always talking about wild swimming? Reach out to them. The neighbour who paints on the wheel in his shed? Offer to bring some wine and see if you’re the company they’ve been looking for.
Emma, a retired editor, had it right: “When I stopped networking and began making friends, life got interesting again. People are more comfortable when you stop trying too hard to impress them.
Amrita, who used to be a solicitor, hit pause on life for a few months. Then, on a dare, she joined a community ceramics co-op. Now she sells hilariously wobbly teapots every Saturday, and says her blood pressure is the lowest it has been in 20 years.
Enough Is Just Right: Perfection Wastes Time
Among the biggest shocks of retirement is figuring out what “good enough” really means. At least at work, the goals were clear: make the sale, reach the target, earn the praise. But then you retire, and you think, ‘Hold on… what does success look like now?’
It might be as easy as saying yes to the first halfway decent restaurant instead of dillydallying for half an hour over reviews, or choosing a comfortable hotel, even if it’s not ideal. Even just picking up a free book that looks cool, instead of chasing the one with all the stickers.
And funny thing: Studies show that those who seek out “good enough” (they are called satisficers) are happier than those who compulsively hunt for the very best (indeed, they are known as maximizers). So if you’re retired or converting in that direction, ease up on the idea of perfection. Good enough may, in fact, be the secret sauce.
The Creative Renaissance You Didn’t See Coming
The act of creating for creating’s sake can be surprisingly powerful. And you don’t have to sell your art or make it perfect; enjoy the process.
Write a silly poem if it makes you smile. Paint something because it feels good. Plant a garden, even if it fails. Sign up for that photography course because you marvel at light.
Richard, a former financial analyst, is carving driftwood into sculptures. “They’re not museum pieces,” he says, “but they’re mine. And I love it.”
No pressure. Just permission to make, because you want to.
The Courage to Be Ordinary
This may be the bravest act: allow yourself to be beautifully ordinary.
Join the book club that does more than read. Sing off pitch in the neighbourhood choir.
Ordinary is where joy hides. Excellence is optional now.
The Next Chapter Begins with A Single Brave Yes
Money and happiness in retirement have nothing to do with what you have and everything to do with having the courage to spend it on the you that is thrilled to be alive.
You’ve spent decades consistently showing up for other people. Now, be brave for you.
The cooking class. On the trip you don’t overplan. The conversation with a stranger. The hobby you abandoned after one month. The memory that will last a lifetime.
Pick one. Book it. Today.
Your analytical mind will want to research every option. Don’t let it. You have the privilege to be a messy, ad hoc, and authentic individual.
Ready to stop overanalyzing and start living?
Take the Creative Retirement Assessment, see exactly what adventure fits your brilliant mind.
Then join the Thoughtful Retirees Community to share this wild, imperfect, beautiful new chapter with others of our kind.
Your mind is brilliant. Your time is precious. Your life is waiting. I’ll be there too. Let’s go.
