Career Lessons I Learned From a Roofing Job Gone Wrong
(Posted on Wednesday, May 14, 2025)
I didn’t land in broadcasting right away.
In fact, it took me four years of doing just about everything but that before I got my first real job in the industry.
Looking back, my younger self seems like a bit of a mess on paper—bouncing between menial jobs, side hustles, and short-lived business ventures. But the truth? I was in motion. Constantly.
→ Trying
→ Failing
→ Learning
→ Starting over again
And while none of those early roles were glamorous, every single one taught me something that I still carry with me today.
One of My First Jobs? Roofing.
More specifically: I was a roofer’s helper for a small local crew, working under a boss who—how should I say this—wasn’t exactly OSHA compliant or emotionally stable.
One morning, one of the work trucks wouldn’t start. He asked me to grab gas to prime the carburetor. So I did.
I found a plastic cup, filled it halfway, and set it down nearby. He picked it up…
…and took a giant sip.
Of gasoline.
What happened next doesn’t even sound real—but I promise it is.
He accused me of trying to poison him. Then accused me of wanting to steal his wife. Then pulled out a pistol and started waving it around. I’m pretty sure he fired into the air. I didn’t stop to find out.
All I knew was that I had been both fired and fired at.
I ran. Fast.
But Here’s the Wild Part: That Job Still Taught Me a Lot
You’d think I would’ve written that whole experience off—and believe me, I tried—but the truth is, even six chaotic weeks on that crew left a mark in more ways than one.
Here’s what stuck:
- I learned how to replace a roof the right way. No shortcuts. No gimmicks. Just hands-on experience and real craftsmanship.
- I got stronger. Eight-hour days hauling 90-pound shingle bundles up ladders in the heat? That built physical and mental toughness I drew on during my college track training.
- I learned to observe people. Not just what they say, but how they move, how they treat others, how they handle pressure.
- I learned that leadership isn’t always at the top. That unstable boss couldn’t lead. But the rest of the crew? They stepped up. They worked with pride. They taught me what they could. They led by example, not title.
One of the older guys pulled me aside before I left and said, “You’ve got something. Keep working hard, but get out of here before this place burns down.”
A week later, they called and said things had “calmed down.” Then added, “Still… probably best you stay away.”
No arguments here.
Sometimes It’s the Crew—Not the Boss—That Sets the Standard
That job changed how I look at work. And leadership. And learning.
The skilled roofers on that team had earned their reputations. They made good money. They stayed in demand. And they held the line on quality, even when the leadership above them faltered.
It showed me something I didn’t fully understand at the time:
You can learn something valuable even from a job that nearly kills you.
Kidding. (Kind of.)
What I mean is—every job, no matter how short or chaotic or unrelated to your future goals, can give you tools that matter:
- Work ethic
- Observation skills
- Emotional intelligence
- Resilience
- The ability to find mentors even in unlikely places
Those skills don’t show up on a résumé. But they show up in your career.
The Real Lesson?
Even the most tedious, dangerous, or menial jobs can teach you something that sticks.
And sometimes—if you’re lucky—you dodge a bullet and walk away with a few tools for life.
So if you’re in a role right now that feels like it doesn’t “count,” take a closer look.
You might be learning more than you think.