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You know what surprised me most about retirement? It wasn’t the extra time or the freedom from alarm clocks. It was how many guys I knew who turned into grumpy old men almost overnight.
These were guys who used to crack jokes on the job site, who could find something funny in a flooded basement or a blown circuit. But once they retired? They turned bitter. Complained about everything. Lost that spark that made them fun to be around.
Not me. I made a decision early on that I wasn’t going to be that guy. And looking around at my Saturday morning breakfast crew, at the guys in my band, at the people who still laugh at life instead of griping about it—I noticed something. The people who keep their sense of humor aren’t just lucky. They do things differently.
They hang around people who make them laugh
My Saturday morning breakfast group has been meeting at the same diner for twenty years. Same booth, same waitress who knows our orders before we sit down. And here’s what matters: we laugh more than we complain.
Sure, we talk about our aches and pains. But mostly? We tell stories. Bad jokes. We give each other grief about everything from golf swings to grandkids. Last week, one of the guys tried to convince us he could still dunk a basketball. We laughed so hard the cook came out to see what was going on.
Compare that to another group I know that meets at the community center. All they do is complain about politics, the weather, their kids not visiting enough. I went once. Never again. Those guys are aging themselves faster than Father Time.
You become like the people you spend time with. If you’re surrounded by bitter people, guess what? You’ll turn bitter too. But if you’re around people who can still find the humor in life? That rubs off.
I’m not saying drop your old friends. But maybe find some new ones too. Join something where people are having fun, not just killing time.
They learn to laugh at themselves
My granddaughter beat me at checkers last week. The eight-year-old. And she didn’t just beat me—she demolished me. Set up a triple jump I never saw coming.
Ten years ago, that would’ve bothered me. I was the guy who had to be good at everything, who couldn’t admit when I didn’t know something. On job sites, I’d pretend I understood blueprints I couldn’t make heads or tails of rather than ask for help.
Now? I told everyone about getting schooled by a third-grader. Made it into a whole story at band practice. Because it’s funny. And because taking yourself too seriously is exhausting.
Getting older gives you plenty to laugh at if you’re paying attention. I can’t remember why I walked into a room half the time. I make noises getting out of a chair that sound like bubble wrap. My idea of staying up late is making it through Jeopardy without falling asleep.
You can either get upset about that stuff or laugh at it. I choose to laugh. My wife Donna and I have a running joke about our Jeopardy scores. She destroys me most nights, especially on literature and art. I get her back on science and sports. We keep score on a notepad, and she’s up by about 200 points for the year. I tell people she’s got a photographic memory. She tells them I’ve got a pornographic memory—I only remember the dirty parts.
They stay curious about the world
One of the guys in my band just started learning Spanish. He’s seventy-one. His grandkids are half Puerto Rican, and he wants to understand what they’re saying when they think he can’t follow along.
Is he any good at it? Not really. But he’s having fun butchering the pronunciation, and his granddaughters think it’s hilarious when he tries to order in Spanish at restaurants.
That’s the thing about curiosity—it keeps you engaged with life instead of watching it pass by. And engagement naturally leads to humor because you’re actually participating in the world instead of complaining about it.
I started writing after I retired. Never thought I’d be the journaling type, but here I am. Do I write anything profound? Probably not. But I’ve discovered that trying to describe the ridiculous things I see every day—like my five-year-old grandson trying to explain cryptocurrency to me—keeps me looking for the funny stuff.
They don’t take everything personally
My eleven-year-old granddaughter told me my music sounds like noise. Not even good noise—just noise. She actually covered her ears during our last band practice in my garage.
Twenty years ago, I would’ve given her a lecture about respecting your elders and appreciating real music. Now? I turned the amp up louder and told her this is what rock and roll is supposed to sound like.
Kids today don’t care about classic rock. Store clerks call me “sir” in that voice that really means “old man.” People explain technology to me like I’m a child. You can get offended by all of that, or you can find it amusing.
I’ve mentioned Jeanette Brown’s new handbook before in recent posts, but it really drives home something relevant here. She talks about how retirement involves a real identity shift, not just leaving your job. You’re literally becoming a different person. And part of that shift, I’ve realized, is deciding whether you’re going to be someone who gets offended by everything or someone who can roll with the punches and find the humor in this weird new phase of life. The guide is free, by the way, and worth checking out if you’re struggling with this transition like I was.
When you stop taking everything as a personal attack on your relevance or value, you free up a lot of energy for actually enjoying life.
They find ways to play
Every Thursday night, four guys who can barely play three chords between us get together in my garage and make enough noise to scare the neighborhood cats. We call ourselves a band. We’re terrible. And it’s the most fun I have all week.
We’re not trying to get good. We’re not booking gigs. We’re just four retired guys playing loud music badly and laughing about it. Last week, our drummer forgot the beat halfway through “Sweet Home Alabama” and just started making stuff up. We kept playing anyway. Sounded like a train wreck, but we couldn’t stop laughing.
That’s what play is—doing something just because it’s fun, not because you’re good at it or because it’s productive. Retirement gives you permission to be bad at things. To try stuff without worrying about looking foolish.
Some guys I know took up pickle ball. Others joined a bowling league. One guy started doing community theater—he’s terrible, but he’s having a blast playing the butler in some murder mystery.
The point isn’t what you do. It’s that you do something that makes you feel like a kid again, even if your knees remind you that you’re definitely not.
Bottom line
Keeping your sense of humor in retirement isn’t about being naturally funny. I know plenty of hilarious guys who turned into miserable old coots once they hung up their work boots.
It’s about choosing to see the absurdity in life instead of the tragedy. It’s about surrounding yourself with people who lift you up instead of drag you down. It’s about being willing to be the butt of the joke sometimes.
Most importantly, it’s about staying engaged with life instead of just waiting it out. Because here’s the truth—retirement can be really long these days. You might have twenty, thirty years ahead of you. You can spend them being bitter about getting older, or you can spend them laughing at the whole ridiculous journey.
I know which one I’m choosing. Even if my granddaughter thinks my music sounds like noise.
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