Yesterday, while working on the set of a local commercial, I was tasked with rolling up 12-foot strips of felt to help the art department wrap out the job. As we sealed it in plastic, I was suddenly back in time (nearly ten years ago) at my hometown flooring-department job, where I spent many days rolling carpet and linoleum.
That wave of nostalgia sent me through my mental résumé, thinking of every job I’ve held since I was a teenage boy. So today, I’m laying out my full work history, from the moment I picked up a hammer (literally) to where I am now.
2011-2015 | Slingin’ Shingles
My first job was with my dad and his business partner at their construction company, B.S. Construction. By the time middle school rolled around, I spent less of each summer with my mom and came home for the back half to focus on football and to earn a little cash before the school year started. I was also growing girl-crazy and eager to spend a few humid nights chasing whatever summer fling might’ve sparked on break.
Their specialty was roofing. Most days I was on ground duty: hauling shingles, fetching tools, and sweeping up the mountain of debris that rained from above. My dad put three of his four boys through that job, and I think we all came out stronger workers because of it.
Despite the swampy Southeast Missouri heat, long mornings, and cheap-buffet lunch breaks, I learned a lot and came to see my father as one of the hardest-working men alive.
2013-2014 | Raising the Bar
In 2013, my parents opened a restaurant in Charleston, Missouri after one of their favorite local bars was set to close. They named it Big John’s Bar & Grill after my dad, whose nickname is Big John. It gave me my first taste of the food-service world; a field I’d stay in for nearly a decade after.
I started as a server alongside my siblings and aunt, then moved into kitchen prep, learning to work a busy line and the skill of keeping customers happy.
2014-2015 | On the Farm
It’s hard to find a teenage boy from the South without at least some farm time, and mine came on a vineyard. A family friend needed weekend help and I needed weekday money, so we struck a simple deal: pack my bags Thursday night and leave them by the door; he’d pick me up after school Friday, swing by for the bags, and we’d spend the evening driving to the farm… and, no bedtime until my homework was finished that night. Saturday and Sunday were all work, sunrise to sunset. Sunday night, he’d drive me back home, ready to start the school week again.
By senior year I’d saved enough and wanted my weekends back with friends, so I stepped away. But he kept me on the books for his wife, who stayed behind to ready their house for sale before moving to the vineyard full-time. I painted, raked, shoveled, swept, mopped… you name it.
Their years of hard work eventually paid off. They turned that vineyard into a full-time winery, a dream they’d been chasing for a long time. Now, they’re retired.
2015-2016 | C(r)ashing Out
In August 2015, I left my hometown for Missouri State University in Springfield, nearly four hours away. My first and only job there was as a cashier at a local grocery store called Price Cutter. It was minimum-wage hell, but it came with two perks: free MD 20/20 for the dorm fridge and a few extra dollars in my pocket.
2017 | Half-Bloomed
My mom spent most of her work career working as a food server for Outback Steakhouse. When I transferred back home to Southeast Missouri State University, I used her connections to land an interview with an old boss of her’s in Cape Girardeau. I aimed to serve tables, but management dropped me into the dish pit. Anyone who’s worked in food service knows that’s the absolute bottom rung.
If I got lucky, I’d spend a shift on cold prep or the Bloomin’ Onion station, but those moments were rare. I was stuck and I knew it… so, I looked somewhere else.
2017-2023 | Rollin’ in Dough
Fed up with life in the dish pit, I left the outback and found a better fit back home. I started at Lambert’s Cafe - Home of the Throwed Rolls (in Sikeston), as a table cleaner, known there as an “extra.” Eventually, I moved up to one of the main roll throwers. If you’ve never been, it’s exactly what it sounds like—I got paid to toss hot, softball-sized dinner rolls across a crowded dining room for nearly five years. (In the video below, skip to 00:14:00 for my beautiful face)
As adulthood closed in and bills stacked up, I took the work more seriously and spent most of my remaining time as a server. That role was less playful but I was good at it, and I enjoyed the independence. You basically worked for yourself, tipping out no more than fifteen percent of your daily haul, and the host stand stayed jammed with guests year-round. It was some of the easiest money you could make, but the ceiling was quite low.
Then, the pandemic hit and the fun was drained out of everything. Relying on tips stopped being fun (not that it ever really was). Working with certain people stopped being fun. Entertaining strangers stopped being fun. The job that once felt like easy money just felt heavy. So, I got my degree and rolled out.
2018-2019 | From the Floor Up
There was an eight-month stretch when I left the restaurant to chase a better-paying job in town with actual benefits. I tried my hand at Lowe’s Home Improvement, a place I knew well because it had long been a second home for my dad. I was hired as a flooring sales associate and, by the time I left, I was drafting invoices for customers and helping organize their full home projects. It was much-more tedious than I expected, and I didn’t like it.
One day, my favorite manager from Lambert’s Cafe talked me into coming back with the promise of a serving position. So that’s exactly what I did, he held up his end of the deal.
2023-2024 | New to Brew City
My partner and I moved to Milwaukee in June 2023, chasing our dream of working in TV, film production, and theater. We didn’t know a single person here when we arrived. So, why Milwaukee? I can’t fully explain it, other than we liked the challenges that lay ahead.
Upon arrival, I leaned on my food-service background and applied to as many downtown restaurants as I could, focusing on the Third Ward; an art-focused area with multiple theaters and studios. That search led me to Merriment Social, a hip spot in the heart of the district.
For the first time I was serving both food and alcohol, and it was TOUGH. I wasn’t used to the drinking crowd (especially Wisconsin), and truthfully I’m still not. But after six months of memorizing cocktail recipes, stumbling through missteps, and slowly getting my footing as a “city boy,” I finally broke into Milwaukee’s TV commercial market.
2024 | Failing Upwards
In January 2024, someone reached out with an internship opportunity at Trusted Media Brands (TMB). Even better, it was for FailArmy, a YouTube channel I’d followed and loved for years. I said yes on the spot.
Before long, I was curating and editing for five of TMB’s social channels, including Family Handyman and The Pet Collective, and spending every other Friday in their Milwaukee studio shooting cooking videos for Reader’s Digest. (In the video below: my favorite FailArmy compilation I produced)
The three-month internship kept getting extended, but by June I gave notice. Commercial sets were finally calling, and I was ready to move on. Editing from home had its perks, but I yearned for the energy of on-site production.
2023-Current | Freely Freelancin’
After leaving the internship, I went all-in on film and commercial production. I received a call from Top Chef for their upcoming season in Wisconsin, a gig that ended with me holding a cocktail on the Caribbean Sea, for the finale episode.
From there I kept saying yes to every crew call across the state: driver, production coordinator, script supervisor, production assistant—anything that put me on set. Each job has meant new contacts, new skills, and fresh proof that I can build a life in this industry without leaving the Midwest. So that’s exactly what I’m doing.
What’s Next?
Looking ahead to 2026, I want to dive deeper into narrative filmmaking as Wisconsin’s new film incentives take effect. I already have one short film, Aroma-Vision (which I wrote), headed for the festival circuit, but there’s plenty more in the tank.
I recently completed my first feature-length screenplay, Wild Horses, and am in pre-production on a political satire short called, The “United” States of America.
Also, I want to explore ways to showcase my writing in the commercial production world. In Wisconsin and many other states, commercial work still drives most of the industry, so moving up in that arena is another key priority of mine.
Sharing my work here on Substack (Belly of the Well) has already opened many doors, and I plan to keep publishing as a way to keep those opportunities growing.