The day I moved into my first apartment, I passed a guy parked under an overpass on the side of the interstate. He stood beside his $200 fishing boat and trailer, staring at a flat tire with the weight of a man whose entire day just got derailed. A new tire probably cost as much as his boat and trailer combined.
That day, as I made trip after trip from my dad’s house to my new apartment, I tracked his progress like a real-life roadside sitcom. The second time I passed, his truck was gone, but the sad, abandoned trailer with its flat tire remained. At first, I wondered if he just gave up, thinking, it ain’t worth it. His flannel shirt and ball cap told me he was the kind of guy who said “ain’t.” He probably also said “gunna,” as in I ain’t gunna fix no damn trailer today, football is on and my old lady’s makin’ stuffed taters.
But at the end of the day, on my final trip, both the truck and trailer were gone. Somehow, some way, he stuck with it. I respected that. Fixing a tire on the side of an interstate isn’t just frustrating—it’s a test of patience, willpower, and blind hope that you won’t end up as roadkill.
Speaking of roadkill, let’s talk about the staggering amount of abandoned furniture on highways. Every week, I see mattresses, La-Z-Boys, and shattered dressers littering the shoulders of the road. Do these people actually think they’ll come back for them? As the mattress somersaults from their truck bed, do they mutter, I’ll swing back later, completely ignoring the laws of physics and common sense? Do they assume the couch that just got sideswiped by a semi is somehow still salvageable?
One day, while driving home from the grocery store, I witnessed the most determined man alive. His mattress had flown off the top of his SUV, but instead of accepting defeat, he stopped and ran back for it. I watched in awe as he balanced it on his head, gripping it with both hands, wobbling back to his vehicle like a suburban gladiator. To his credit, he saved the mattress. However, he did not save his dignity—his pants, along with his cargo, were in dire need of a tighter belt.
I can already hear you asking, OK Greg, where is this headed? Well, I own a ski boat and recently bought a utility trailer for lawn maintenance at our rental property. The moral of the story? I don’t want to be Trailer Guy.
Once upon a time, I shared a fishing boat with my buddy Scott, aka “10-Page Letter Scott.” His childhood trauma involved a catastrophic trailer failure on a family trip to Minnesota—bearings fused, wheels locked, and an entire day and a half lost to the chaos. That experience left him permanently scarred. Thanks to him, I now have a ritual: repack bearings every winter, grease them after every trip, and double-check ratchet straps like my life depends on it.
Because the last thing I want to do is provide some soccer mom in a minivan with an unintentional buzz cut when my lawnmower flies off the back of my trailer.
Want to hear more hilariously relatable stories? Listen to Episode 55 of Welcome to the Suburbs on our website https://suburbspodcast.com/ or your favorite platform, like Apple Podcasts https://podcasts.apple.com/us/podcast/season-3-episode-55-setting-picks-kayak-retaliation/id1669816704?i=1000693022593
