What I learned from sitting around for six months straight
Right. Retirement.
They sell it to you like it’s the promised land, don’t they? Endless freedom. No alarm clocks. Golf on a Tuesday morning while everyone else is stuck in traffic. Living the dream, they say.
What they don’t tell you is that dreams can be catastrophically boring.
One minute you’re a functioning member of society with meetings and deadlines and people who need things from you. The next, you’re standing in your kitchen at 11 am on a Wednesday, wondering if organizing your sock drawer alphabetically is finally the day you’ve officially lost the plot.
Winston Churchill called it the “Black Dog” of despondency. I call it “realizing you’ve become spectacularly irrelevant and there’s precious little you can do about it.”
Cheerful stuff, this retirement business.
The Existential Horror of Tuesday Afternoons
Here’s what nobody tells you: work gave your life structure. Not just the 9-to-5 bit, but the whole edifice of it.
The alarm clock that told you when to wake up. The commute that made you feel productively martyred. The meetings that were mostly pointless but at least gave you something to complain about. Even Gary from IT, the complete numpty—at least Gary gave you a reason to exist, if only to avoid him in the corridor.
Strip all that away, and what have you got?
Daytime television. That’s what.
I spent my first week of retirement watching something called “Homes Under the Hammer” at 10 am. Do you know what this is? It’s people buying derelict houses for £80,000, spending £40,000 doing them up, and then acting surprised when they don’t make a profit.
It’s absolutely riveting, obviously.
By week two, I’d watched every David Attenborough documentary ever made. By week three, I was seriously considering whether I could train the local pigeons to perform synchronized swimming. Would’ve given me something to do, at least.
The real horror isn’t the boredom itself. It’s the creeping realization that this is it now. This is your life. Every day, forever, until you keel over in the frozen peas section at Sainsbury’s.
Motivational, isn’t it?
The Identity Crisis (Or: Who Am I Without My Email Signature?)
For 40 years, I had an answer to the question “What do you do?”
Now? I’m just some chap who used to do something interesting but doesn’t anymore.
“I’m retired” feels less like a status and more like an admission of defeat. Like saying “I’m surplus to requirements” or “I’ve accepted my irrelevance with grace.”
I went to a dinner party—terrible decision, never again—and someone asked what I did. “I’m retired,” I said, like I was confessing to a crime.
“Oh lovely!” they said. “What do you do with all your time?”
What do I do? WHAT DO I DO?
Well, Sandra, on Monday I reorganized the garage.
On Tuesday, I considered reorganizing it again because I wasn’t happy with my initial decisions.
On Wednesday, I had a 45-minute argument with myself about whether to go to the shops at 2 pm or 2:30 pm.
On Thursday, I lost the argument.
It’s absolutely thrilling, let me tell you.
The worst bit is running into former colleagues. “How’s retirement treating you?” they ask, with that peculiar mix of envy and pity.
“Marvelous,” I lie. “Simply marvelous. Never been busier.”
Been busier doing what, exactly?
Contemplating whether to have lunch at noon or 12:15?
Revolutionary stuff.
Three Ways to Prevent Yourself From Going Completely Mad
1. Get A Side Hustle (Or At Least Pretend To Be Busy)
Now, I know what you’re thinking: “Side hustle? That’s for millennials with podcasts about their feelings.”
Wrong.
A side hustle is the only thing standing between you and becoming one of those people who comments on Daily Mail articles at 11 am.
The key is finding something—anything—that makes you feel vaguely useful. Something that pays you actual money, proving you haven’t been completely abandoned by capitalism.
I started with consulting. Charged extortionate fees to tell people things they already knew. Felt fantastic. Highly recommend it.
Then I discovered I could write. Not Dickens, obviously. More like strongly-worded emails but longer. Turns out people will pay for that. Who knew?
The beauty is: you can do it in your pajamas. You can tell difficult clients you’re “fully booked.” You can work Tuesday afternoon and take Friday off entirely to watch Grand Designs and judge other people’s architectural decisions.
It’s not about the money, though the money’s nice. It’s about proving to yourself that you’re still capable of creating value, even if that value is explaining to someone why their business plan is fundamentally ridiculous.
The first hundred quid you earn? Transformative. Not because you need it—you don’t. But because it proves you’re still in the game. Still got it. Still relevant.
Take that, Gary from IT.
2. Start Small Projects (Because Big Ones Require Effort)
My first mistake was thinking I needed a grand purpose. Write a novel. Climb Everest. Learn Mandarin while standing on one leg.
Absolute nonsense.
What you need are small, achievable projects that make you feel slightly less useless:
Learn something pointless but impressive — I taught myself to identify 50 different types of clouds. Why? Because I could. Does it matter? Absolutely not. Can I now bore people at parties? Tremendously.
Fix things you’ve been avoiding — That squeaky door hinge? Fixed it. Took 5 minutes. Felt like I’d rebuilt the Sistine Chapel. The bar is very low now. We take our victories where we can find them.
Physical activity that isn’t humiliating — Swimming. Three times a week. Not Olympic standard. More like “thrashing about and hoping not to drown.” But it’s structure, isn’t it? And it stops you from having elevenses and twelvenses and ones-ies.
Create something ridiculous — I’ve started writing. These very words you’re reading. Started as therapy. Turned into something vaguely productive. Would recommend.
The trick is making yourself do something—literally anything—that isn’t watching property programs or scrolling through news about things you can’t change.
Small victories accumulate. Before you know it, you’ve gone a whole week without contemplating the meaninglessness of existence.
Progress.
3. Master The Art of Productive Laziness
Here’s the controversial bit: not every minute needs to be filled.
You’ve spent decades being busy. Being important. Being needed.
Maybe—and this is radical—you could just… stop?
I don’t mean vegetate. I mean proper rest. Reading actual books instead of skimming headlines. Thinking about things that aren’t work or money or that weird noise the car’s making.
When you’re bored, pick up a book, not your phone.
Reading is how you absorb years of someone else’s experience without having to live through their mistakes. Much more efficient. Plus, it makes you look intellectual if someone catches you at it.
I’ve also discovered what I call “strategic contemplation.”
Other people call it “staring into space.”
Same thing, really.
Twenty minutes of just thinking.
No agenda.
No goal.
Revolutionary.
The key is distinguishing between productive rest—reading, learning, pondering life’s mysteries—and destructive laziness, which is watching clip shows about Britain’s worst drivers while eating biscuits at 3 pm.
One fills the void. The other just makes you fatter and sadder.
Neither is ideal, but at least one leaves you with something resembling dignity.
The Weather Pattern Theory
Spent enough years observing life, you learn to read patterns.
Retirement’s got weather, just like anything else.
Some days are clear sailing—you wake up with energy, purpose, a plan. Everything feels right. You’re productive. You’re engaged. You’re winning at retirement.
Other days? Storm’s brewing. Black Dog weather. You feel it before you see it—that restlessness, that sense of unease, the pressure building.
I’ve learned to read the signs.
When I start reorganizing things that don’t need organizing—that’s a warning.
When I’m checking email every five minutes for messages that aren’t coming—time to change course.
When I find myself watching daytime television and actually caring about the outcome—critical situation. Immediate action required.
The trick isn’t avoiding the storms—they’re going to come regardless.
The trick is learning to navigate them.
Batten down the hatches. Do something productive. Call someone. Read something. Fix something. Create something.
Wait for better weather.
It always comes.
The Uncomfortable Truth
Right. Cards on the table.
Retirement is weird. Really weird.
Some days are brilliant. You wake up, the sun’s out, you’ve got projects, you feel purposeful. Life’s good.
Other days? Black Dog weather. Everything feels pointless. You question every decision that led you here. You wonder if you’ve peaked and it’s all downhill until the grave.
Both are true. Both are valid.
The trick—and this took me months to figure out—is accepting that you’re allowed to feel both. You don’t have to be grateful every second for your “well-earned rest.” You’re allowed to miss being needed. You’re allowed to be bored.
But you also can’t just surrender to it.
You need a plan. Doesn’t have to be a good plan. Just a plan.
Small projects. Side hustle. Books. Strategic thinking time. Avoiding people who ask what you do with all your free time.
That’ll do.
The Final Word
So here we are. Retired. Free. Master of our own destiny.
And spectacularly uncertain what to do with any of it.
The “Black Dog” Churchill mentioned? It’s real. But it responds to action. Even small, slightly ridiculous action.
You’ve spent your whole working life being told what to do. Now you get to decide.
Some days, you’ll decide to do something productive.
Other days, you’ll decide to watch Homes Under the Hammer and judge people’s renovation choices.
Both are valid life decisions.
The point is: keep moving. Keep trying things. Keep finding new ways to avoid becoming that person who alphabetizes their spice rack because they’ve literally run out of other things to do.
You earned this freedom. Don’t waste it proving that humans aren’t actually designed to have this much leisure time.
The Black Dog can be managed. The void can be filled. The boredom can be beaten.
You just need a strategy. And possibly a sense of humor about the whole absurd situation.
Now if you’ll excuse me, I’ve got a date with some clouds that need identifying.
Cheers.
An Idea: From staring at the blank page… to actually getting paid
A few months ago, I sat there with the same thought most of us have:
“I’d love to write, but where on earth do I even start?”
I kept circling the same three questions:
Why would I write in the first place?
What would I actually write about?
And how would I turn that into something that earns money?
Here’s what I figured out (and what I wish I had from day one):
First, the why.
If you’ve ever wondered why people like me keep showing up to write, I’ve put together a free report that explains it. Grab it here.
Next, the what.
Knowing your reason is one thing, but deciding what to write about is where most people get stuck. I created a guide that shows you how to choose a niche that fits you. It’s less than a Starbucks coffee. See the guide here.
Finally, the how.
Once you know why you’re writing and what you’ll focus on, the last step is learning how to actually do it — quickly, without wasting months. I’ve broken that down into a simple process you can follow in an afternoon. For less than a burger meal, you could be publishing and earning. Find out how here.
That’s the exact path I took — and if you’ve been circling the same questions, now you’ve got the answers laid out in front of you.