Everything I Know in Life I Learned from Kenny Rogers’ “The Gambler”

please help, I am appallingly incompetent

It Just Isn’t Enough

“You’ve got to know when to hold ‘em, know when to fold ‘em, know when to walk away, and know when to run.”

That’s it. That’s all I know. And it’s not helping.

No one tells you how often you’ll need to parallel park under pressure. Or that there are at least six different types of insurance you’re supposed to have just to exist. Or that if your landlord starts a sentence with “technically,” you’re already screwed.

Kenny tried his best but he didn’t prepare me for any of that. He gave me a vibe. A swagger. Aura. A bit of campfire wisdom wrapped in outlaw cool. But he didn’t teach me how to cook a vegetable without YouTube. How to tell if someone’s flirting with me or just Canadian.

I tried using it in a job interview.

“What would you say is your greatest strength?”

“Well,” I said, leaning in with the quiet gravitas of a man who’d seen the music video, “I don’t count my money while I’m sittin’ at the table.”

They said they’d be in touch.

Now, in a different world — say, Mr. Rogers’ Neighborhood, except Mr. Rogers is Kenny Rogers — that might work. That would be a beautiful, denim-and-soft-guitar utopia where calm wisdom and outlaw gambling metaphors coexist in harmony. But it’s not that world. I don’t live in a world run by kindly gamblers with gentle baritones. I live in this world, where Kenny’s advice only applies in an incredibly narrow window of situations — and, tragically, I am never in those situations.

I once ghosted a dentist because the reminder email said “confirm or reschedule” and all I could think was “you never count your money while you’re sittin’ at the table.” That felt right. That felt wise. Now I have three cavities.

I tried dating. First date told me she was looking for someone with a plan. I told her, dead serious, “Every hand’s a winner, and every hand’s a loser.” She blinked like I’d just quoted scripture from a cult and asked if I was okay.

I am not okay.

I’m a drifter with a very specific moral compass that only points toward vaguely metaphorical poker tables. At worst, I’m a man who thought a 3-minute country song would suffice as a personal ethos and life plan.

Spoiler: it does not.

Still, I press on. Because somewhere in the folds of that beard and the brim of that hat, Kenny whispered the closest thing I’ve had to an epiphany:

You never count your money while you’re sittin’ at the table.

I don’t even know what it means, but damn is it sexy.

So when life deals me another busted grocery cart or a car that won’t start or a breakup text that just says “k bye,” I whisper back:

“Gotta know when to fold ‘em.”

Then I run. Usually into traffic. But with purpose.