Everyone told me to plan for retirement. Save enough, calculate the numbers, sort the pensions.
Nobody told me what to actually do with 20+ extra years.
Six months in, I sat at my kitchen table on a Tuesday morning, financially secure and utterly lost.
The spreadsheets answered how long my money would last.
They didn’t answer what I was supposed to do with all those Tuesdays.
Then I found three unlikely guides: death, YOLO, and FOMO.
I know how that sounds. Bear with me.
Death as the Most Honest Teacher
When you’re twenty, you think you’re immortal. Another summer always comes. Another chance to travel, learn that language, repair that friendship.
At sixty-seven, I know better.
There are only so many summers left. The math is unavoidable. That realization could be depressing, but I’ve found it oddly liberating.
I started asking: If I knew I had fewer years than I hoped, would I still spend today this way?
That question cuts through nonsense fast. It makes me less tolerant of things that drain me—pointless arguments, empty obligations, clutter (physical and mental). It makes me more protective of things that matter: conversations over tea, long walks, creative work that leaves something behind.
Death isn’t morbid when you use it as a filter. It’s clarifying.
Retirement isn’t about stretching time out. It’s about filling it well.
YOLO Isn’t What You Think
“You only live once” sounds like something shouted by twenty-somethings on a stag do in Ibiza.
But at sixty-seven, YOLO carries different weight.
It’s not about bungee jumping or buying a sports car.
It’s about permission—permission to say yes to things I once thought impractical, frivolous, or “not for people like me.”
YOLO is why I started this newsletter.
Not because it’s sensible or lucrative, but because I wanted to. Why I learned basic AI and database management at sixty-seven.
Why I meet friends now instead of putting it off.
Not recklessness. Appreciation.
YOLO in retirement translates to: Do it now while you can. Not in panic, but in recognition that “later” isn’t guaranteed and “someday” is a lie we tell ourselves.
I still weigh risks. I’m not an idiot. But I’m less willing to delay things that matter.
Because unlike when I was twenty, I know I only live once now. The math proves it.
FOMO Hits Harder After Sixty
For years, I thought FOMO was a young person’s curse—anxiety about missing the party, the promotion, the Instagram moment.
Turns out, FOMO gets sharper with age.
I’m acutely aware now: there are books I’ll never read, places I’ll never visit, projects I’ll never start. Not because I’m lazy, but because time is genuinely finite.
The risk isn’t missing one event. It’s missing entire dimensions of retirement because I was too cautious, too distracted, or too stuck in routine.
So I’ve learned to use FOMO as a compass: If the thought of not doing something nags at me, it’s probably worth doing.
Not everything. I can’t do everything. But the things that whisper “you’ll regret not trying this”? Those get priority now.
How They Work Together
Here’s how death, YOLO, and FOMO intertwine for me:
Death whispers: Don’t waste time.
YOLO shouts: Say yes while you can.
FOMO reminds: You’ll regret what you don’t try.
Together, they’ve helped me clarify what I actually want from retirement:
I want:
Time with people who matter (conversations, walks—irreplaceable)
Experiences that enrich, not just fill time
Creative work that leaves something behind
Learning (badly at first, that’s fine)
I don’t want:
Busywork disguised as purpose
Comparisons (someone else’s retirement isn’t my measure)
Clutter (physical, mental, or social)
Simple. Clear. Harder to execute than you’d think.
The Uncomfortable Truth: Paralysis of Choice
Here’s the downside nobody mentions: too many options.
Thinking about death, YOLO, and FOMO reveals there are hundreds of things I want to do. That leads to paralysis. Too many paths. Fear of choosing wrong. Fear of wasting precious time on the wrong thing.
It’s a problem.
But it’s also—and I realize how this sounds—a nice problem to have.
Better than sitting at that kitchen table six months into retirement, staring at the wall, wondering what any of this was for.
Retirement as a Limited-Edition Gift
Here’s the perspective these three ideas gave me:
Retirement isn’t a blank stretch of years. It’s a limited-edition gift.
The scarcity makes it valuable. If I had infinite time, I’d waste most of it. Knowing I don’t forces me to decide—consciously, deliberately—what matters.
Death, YOLO, and FOMO aren’t morbid or reckless. They’re reminders that life, at any stage, is fragile, fleeting, and therefore worth grabbing with both hands.
The Question I Ask Myself Now
When I look at my days, I ask:
Is this how I want to spend one of the irreplaceable pages in my retirement story?
If yes, I’m on the right path.
If no, I change something.
Retirement isn’t about drifting.
It’s about choosing.
And sometimes, the best guides for choosing are the things we once tried to ignore.
What About You?
How do you decide what really matters—in retirement, or wherever you are now?
Do death, YOLO, or FOMO influence your choices?
Or do you use different filters entirely?
I will give you an example.
A few months ago, I wrestled with three questions:
Why write?
What about?
How do I earn from it?
I cracked the code — then packaged the answers so you don’t waste months like I did.
For readers who like to go deeper, I’ve also collected some extended guides at my Gumroad page — small tools for thinking and creating in an age that moves too fast.