Growing up in the hollers of southern Indiana, Stephen Wilson Jr. was a golden-gloves boxer. When it became clear he wasn’t going pro, he enrolled in Middle Tennessee State University, where he studied microbiology. He took a job in research and development for Mars, the company behind candy and pet food.
His crowning achievement—inventing a dental dog treat, Dentastix Fresh, which is still on shelves today.
But at age 37, Wilson quit to pursue his dream. A decade later, he’s taking over country music, although Wilson is proud not to fit into a single genre; something true of his music, and his life.
Wilson has been writing poems and songs since he was a child. He taught himself guitar. He played in a band in college, but then shelved it for a career.
Fast forward to now: he’s nominated for 4 CMA awards including New Artist of the Year. He’s recorded with Miranda Lambert. He’s on a world tour that runs from Belfast to Paris to Oslo. He’s developed a voice straight from the Heavens.
He’s 47 years old.
Wilson’s breakout performance, in November 2024, was an acoustic cover of the song Stand By Me by Ben E. King. It’s entirely fitting. His journey shows that life is long; you can’t be afraid, you’ve got to keep fighting, you’ve got to be willing to have your own back, to stand by yourself.
3 Crucial Lessons from Stephen Wilson Jr.
Lesson one: Progress is non-linear. The idea that you have to leave behind your passions when you grow up is nonsense. If you keep showing up, growing, and finding a way to do what you love, you never know what can happen next. So much of extraordinary success is the result of extraordinary persistence; it’s simply staying in the game.
“You’re not stuck in any particular life. You can live multiple lives, you can do all kinds of things,” says Wilson. “Life has chapters, it’s not one chapter.”
Wilson bought his guitar for $400 on Craigslist. He picked it up from a parking lot in Nashville. It’s held together with masking tape.
“Guitars are meant to be played, not hung up on a wall,” he explains.
Lesson two: Wilson’s guitar is a metaphor for his story, and really, for so much of life. You can protect yourself. Quit on yourself. Stay polished. Stay safe. Stay away from your dreams. Keep the guitar on the wall.
Or, you can let yourself get used up doing what you love.
I recently turned forty. I am fortunate and have a beautiful life. But sometimes, and more often than I’d like, I find myself feeling burnt out and exhausted. I suspect that underneath these feelings is a concern that maybe this is it. Maybe there’s nothing more in the creative tank. What if I’ve peaked? It wouldn’t be the worst thing, but I’m a pusher, I’m inspired by growth.
But then I listen to Wilson’s singing, songwriting, and guitar playing. I watch him perform. And I am inspired. This guy emerged in his late forties! There is so much more in the tank!! Life is short, but it is also long. It’s not naïve or cliché to keep dreaming; it’s actually essential.
Lesson three: Don’t let fear hold you back. When you hold yourself back because you are worried about failing or looking ‘uncool,’ you sacrifice growth, mastery, fulfillment, richness, love, and all the other good stuff in life for short-term comfort and safety.
It’s a trap. Get over it.
Wilson was in a massive corporation making dog treats. It would have been easy for him to say, My glory days are over. I was a boxer. I played in a band. I had a good run. Why try? Why risk embarrassing myself?
And the truth is, he might have embarrassed himself. Most people don’t make it to the top of the charts. But who cares?! You might as well take your shot.
Fear, doubt, and insecurity are all parts of human nature. It’s easy to give up on yourself, to go through the motions and be superficially cool (but actually boring). The older you get, the more enticing the path of least resistance becomes. But you don’t have to follow it.
You can keep trying. You can step into the arena, lay it on the line, make yourself vulnerable, and fully live your one and only life.
You don’t get unlimited chances. But if you’re willing to take them, you get more than you think.
Thank you, your post feels timely to me, especially the third to last paragraph with "the more enticing the path of least resistance becomes." I sense I have shifted from being a restless adventurer who needs to get *out there* to a more timid homebody (and I'm feeling that especially this morning as I cope with nerves about traveling solo to the Javelina ultra this weekend, where the scene feels intimidating whereas the younger me would've found it exciting). And, the video inspires me because I'm a beginner guitar player, just three months into lessons. I was at a weird AirBnB the night before an ultra in mid-August, and a guitar hung on the wall as decor, and out of boredom and curiosity, I took it off the wall and played around with it. That was the first step. Now I'm taking lessons and feeling alternately inspired and frustrated. But I'm learning and making (very slow) progress. Your post is a motivator to show up to the starting line Saturday, thanks again.
Fantastic piece. On a long drive back from Massachusetts late yesterday, I played son of dad (deluxe) start to finish. SWJ is simply extraordinary.
The first time you head down the Stephen Wilson Jr rabbit hole you will get lost for 90 minutes finding one incredible song after another. As I did about 15 months ago. Also, his interview w/ Howard Stern is well worth the time.
Sturgill Simpson (Johnny Blue Skies) had a somewhat similar unconventional career path.