The off-season. No one likes to talk about it, but unless you’re rolling in cash or living off the grid, you need to scrape together money to keep chasing winter.
We’ve done it all. Some jobs were fine, some were soul-sucking and some were so bad they’re now just running jokes between us.
Here’s a few that still stick with me.
The Mascot
One summer, I somehow ended up in a full-body hot dog costume handing out coupons at a car show. It was 100-degrees out, I couldn’t see properly and a seagull attacked me because it thought I was holding actual food. I lasted four hours before taking my “smoke break” and never going back.
The Model
One summer, a friend of a friend roped me into “modelling” for a local ski shop’s new website. It sounded cool until I realized it wasn’t high fashion – it was me standing in a scorching parking lot wearing ski jackets while a guy yelled, “Look more natural!”
At one point, a gust of wind flipped my hood inside out and I somehow ended up looking like a deranged Jedi in every photo. The worst part? They actually used those photos. I’m still haunted by the image of me sweating buckets, trying to smile like I wasn’t slowly baking inside a down jacket. And no, I won’t be linking to them!
The Stinker
One summer I took a job cleaning rental cars at the airport. I thought, “How bad could it be?” The answer: horrific. By day three, I was knee-deep in spilled milk cartons, half-melted chocolate bars, used diapers and the smell of something that can only be described as “human sadness.”
I lasted 2 days.
Michael still teases me about it.
I came home one night, threw my uniform in the bin, and swore I’d never step foot in a Hertz parking lot again.
The Clowns
One summer, we both took a gig as kids’ party entertainers because someone told us “it pays well and is easy.” Lies. Nothing in life is as chaotic as trying to control a dozen five-year-olds armed with cake, sugar and zero fear.
We were dressed as “outdoor adventurers” (random hats and oversized vests) and told to “teach fun wilderness skills.” Within ten minutes, the kids had stolen our rope, tied M to a tree, and were using my backpack as a soccer ball.
At one point, a kid looked me dead in the eye and asked, “Are you even a real clown?” I’m not. But it stung regardless.
We lasted three parties. Barely.
The Muffin Man
Michael once decided to take a job as a dishwasher in this sketchy café run by a guy who thought hygiene was optional. He lasted two weeks, mostly because the boss paid him in loose change and leftover muffins. He spent most of that cash on skate parts, which broke immediately and then swore off dish pits forever.
The Surprise Winner
Not all the jobs were terrible. I once did a summer gig painting houses with a crew of total weirdos, and it was actually… fun? We’d finish early, sit in the shade, and talk about our next winter trip. The pay was okay, but the vibe was good and sometimes that’s all you need.
The Musician
Michael once tried busking with a ukulele because he figured “how hard can it be to learn three chords?” Harder than he thought. After an hour of butchered Jack Johnson songs, he made exactly 87 cents and a free half-eaten burrito someone left in his case. He never mentioned it again.
The Perfect Job
Not all jobs were awful. We did a summer at a lakeside gear shop where the manager didn’t care if we spent half the day paddleboarding “to test rentals.” It paid peanuts but it almost felt like cheating.
Final Thoughts
We’ve done some truly questionable jobs in the off-season. Some were boring, some were brutal, and a few were just straight-up ridiculous. But they all gave us stories we’ll be telling forever.
Summer jobs are just part of the deal when you’re trying to keep the winter dream alive. You grind through the weird gigs, pocket what cash you can and come out with a few scars.
What about you? What’s the worst summer job you’ve ever done? The comments are open!
