It Happens, and Retirees are Revolting.

I don’t mean revolting as in disgusting, like “There’s a revolting smell in the air and I think it’s that old guy.” I mean revolting as in “Viva la revolucion!” Revolting against the norm. Revolting against stereotypes. Revolting against — retirement! Why? Because for many, retirement isn’t what it’s cracked up to be.

Retirement’s the Dream, Right?

Not so fast. We’ve been told that fairy tale so often it’s become ingrained in our collective psyche, etched in our hive mind. You punch out for the last time, trade the morning commute for lazy coffee refills, and finally relax. Except, for a lot of people, retirement sucks like an Electrolux.

Millions walked away from work during the pandemic. But 1.5 million jumped right back into the fire by 2022. Sure, some needed the cash, but nearly half came crawling back for something else like, oh, say, purpose, camaraderie, the simple thrill of doing something that mattered.

“Dave, give me an example or it didn’t happen.” Okay, here are two: There was a doctor who left her job only to return to work as a traveling physician. She found that too much downtime is its own kind of nightmare. Then there was a retired couple who stumbled into a lucrative consulting gig, realizing work on their own terms was better than no work at all.

Maui Wowie

I was in Maui. Family vacation. The kids were younger. The tiki torches were lighting up the night sky and daddy needed to be just as lit. Yes, it was that kind of day. So I did what any red-blooded mainland dad does while vacationing in the aloha state with a pair of tiny humans and a harried spouse – I went to the hotel bar and ordered a cocktail tropicale.

But this was no ordinary run-of-the-mill umbrella drink. I ordered a cauldron of booze, a vessel of liquid merriment, a chemical concoction with a Heinz 57 mix of liquors — plus a Bacardi 151 rum floater, just for good measure. “And make sure you put it in a freakin’ pineapple!” I barked to the bartender.

Moments later, I stepped into the elevator toting my pineapple the size of Sponge Bob’s house, and headed up to my rum, I mean, room. A fellow tourist stood inside. He was older, in his 60s, rotund. He wore a Hawaiian shirt, shorts, sandals, and a look on his sun-blistered face that betrayed the laid-back nature of his sartorial style.

Without missing a beat, like we’d been locked in conversation for hours, he turned to me. “Don’t ever retire,” he said, shaking his head. “I retired four months ago and I regret every waking minute.”

Before I could even respond with a polite head bob, the elevator stopped and Mr. Jolly Golightly stepped off without saying another word. I continued to my floor, to my room, to my kids, to my wife, to my…life. His words rang in my ears, and his negative vibe clung to me like smoke. It was a “wowie” moment, for sure. And if there was ever a time for a nice fat blunt of Maui’s finest, that was it.

“Don’t retire from something…

…retire to something.” That’s the mantra we’ve all heard. It’s lost a bit of its freshness over the years, but you know what? It’s true. Retirement—when done right—isn’t a slow fade to black. It’s a second act, a reinvention, a well-earned middle finger to alarm clocks and office politics.

The happiest retirees aren’t parked in La-Z-Boys watching the world go by. They’re out there doing, creating, pushing forward, even if it’s just in their own quiet, satisfying way. They move their bodies. They keep their minds sharp. Not just with Sudoku, but by engaging with the world, staying curious, staying hungry.

And they have real connections in their lives—friends, partners-in-crime, people to grab a beer with on a Tuesday afternoon. Solitude is great, but isolation is deadly.

The Key to Retirement

Wake up with a purpose. That’s the key. Have structure, but not so much that it feels like prison. Have freedom, but not the kind that leaves you staring at the ceiling at noon, wondering what the hell to do with yourself.

Retirement is the time to finally live on your own terms. Chase a paycheck, chase a sunset, chase the perfect Mai Tai—just chase something.

But beware of retirees on Maui elevators. Some of them have seen the other side of boredom. And trust me, it ain’t pretty.

Image: Shahnawaz Hussain/Vecteezy