The job was only dangerous the way I did it. Working for my dad's siding business during high school and college summers, I once fell backwards off a scaffold into a bush after losing my balance while working on a window. The bush "caught" me. I couldn't reach the ground or the scaffolding ladders. Suspended like a fly in a spider's web, I panicked for a few seconds before finally wriggling free to solid ground.
Another time, I jumped from scaffolding after scraping a power line, tripping it and knocking out the power in the house we were working on. I'm lucky the house didn't catch fire—and luckier still that I wasn't electrocuted.
The closest I came to serious injury was at our own home. Alone in the yard, 15 feet up a ladder against the house, I was ripping off the yellow siding that had uglified it since before I was born. One nail wouldn't budge. I pulled, pushed, even cursed it with every combination I knew. Nothing.
I wedged the claw as deep as possible, thrust my hip into the ladder for leverage, and yanked with both hands. Growling, I leaned in—and then the claw slipped off. THWACK! The hammer struck me square between the eyes.
Yes, I hit myself in the face with my own hammer. Really, really hard.
The impact threw me off balance—15 feet up a ladder—and I started falling backwards. At the last second, I grabbed the ladder with both hands to arrest the fall.
Now, as a solopreneur, whenever I mess up—a botched pitch, awkward transition, poor interview—I remind myself: This isn't as bad as that.
For most of my life, I saw this siding work as just a summer gig. But seven years ago, when I launched my own venture, something surprising happened: I started channeling my dad's approach. Nearly 30 years later, I'm applying lessons I didn't even realize I'd absorbed.
***
My dad, now 81 and retired, is old-school blue-collar. He'd laugh at "solopreneur" as a made-up term and scoff at calling his work (siding! windows! trim! gutters!) the gig economy.
If you'd told us back then that those jobs would inform my writing business, we'd both have chuckled. He viewed it as education in manual labor to push me toward college. I loved the transformation: starting with a shabby house and leaving it transformed and beautiful.
But the real education was unexpected. Take late-paying clients—I've been fortunate, never stiffed. I sometimes chase payments with follow-ups, but it doesn't faze me. That's partly because Dad paid customers... and how he paid me.
He paid $5 an hour (big money for a teen in the late '80s/early '90s). I tracked hours on cardboard scraps from siding boxes. Every two weeks, I'd total it and hand it over. He'd pay when he got paid... if he remembered. When I nagged (circling back, checking in!), he'd shrug: "Better you chase it than get it wrong."
No client's tried that on me yet. But I'm ready.
***
Trades wisdom: measure twice, cut once. Crucial in siding—you get paid the same whether it takes a week or a month. Extra fixes eat margins. I measure twice; in writing, I plan deeply before typing: measure twice, write once.
Not foolproof—sometimes I still err. But efficiency meant more money with Dad, who worked fast his whole life. He'd rib me for slowness: "What took so long on that siding?"
Me: "I nearly killed myself with a hammer and fell off the ladder."
Yet he'd "waste" hours chatting—with clients or at Ingram Wholesale Siding, our supplier. We visited weekly: pre-job buys, mid-job pickups, post-job drop-offs. Dad and the guys would talk endlessly.
I didn't mind—the less ladder time amid accidental blackouts, the better.
He could've saved time/money at big-box stores or with deliveries. But working with Dad showed me his world beyond fatherhood, especially at Ingram. I saw how he connected: joking, asking about lives, paying a premium to support the "little guy" over chains.
Those ties ensured favors: rushed orders, extended terms, deliveries. It hit me recently: Dad was a networking master.
***
Beyond speed, Dad modeled hard work as part of life—not the center. We left at 7:30 a.m., home by 4 p.m. daily, in time for dinner.
With three brothers in sports, he missed zero games for work—only if at another's. Cherished memories: pre-dinner sidewalk fishing with him and my older brother.
I now see this as his choice: work more or be present. He chose us. That's the top lesson.
"Don't smash your face with a hammer" is a close second.
Matt Crossman
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Matt Crossman is a St. Louis-based writer specializing in sports, travel, adventure, and professional development. Email him at matt@mattcrossman.com
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