Four days a week, Billy Bannon drives two to three hours each way into a California state prison. Once he’s inside, he spends three or four hours teaching DJing and music production to men who are incarcerated. Then he drives home.

That alone could carry an episode. But I’ve known Billy since middle school in Sudbury, and I know where this story started. The kid I grew up with would have bet his life savings he’d never be a vegetarian. Yoga instead of basketball? Not a chance. California? He thought California was stupid. Even the 2016 version of Billy didn’t see this coming.

The expected script for a coach goes like this: win a national championship, then climb. Billy won the 2010 NCAA Division II title as associate head coach at Cal Poly Pomona. Two years later he walked away from the dream job.

His 🔄 Flipped Story isn’t about leaving coaching. Billy never stopped being a coach, and he never stopped being a teammate. He lost the team, and then he rebuilt one in a place nobody would have predicted.

Losing the Locker Room

Billy had been on a team since 1981, first as a player and then as a coach. Of all the wins and titles, being a good teammate is the one thing he’d hang his hat on.

“If there’s one thing I would want to hang my hat on… it would be that I was a good teammate.” — Billy Bannon

What he didn’t see coming was how much of his discipline belonged to the team. When other people need you to show up and play hard, you show up and play hard. After coaching, he was a free agent. He was filling his bucket month to month, and he started missing his own marks.

So he built a new practice around what he calls self-integrity: holding himself to the standard a locker room used to hold him to. Then he went and found a new team. First it was the veterans, then the men inside, then Prison Yoga Project and Give a Beat. He’s in the room every week because those guys are counting on him. In other words, it’s coaching.

The Regret Test

“What would happen if I just went for it?”

Billy has asked himself that question at every major turn. At 25, he had a good path laid out at home in teaching and high school coaching. He packed his great aunt’s 1979 Dodge Aspen and drove west with no job, no place to live and a couple thousand dollars. He didn’t want to be 50 someday wondering what would have happened.

He asked it again in his late thirties. By then he’d watched older coaches get bounced from school to school, and he’d seen friends fired after three seasons and left scrambling. He gave himself one full season to look honestly at the next 20 or 30 years. Then he gave himself one more and told almost no one.

This isn’t a “blind f-it,” as Billy puts it. It’s refusing to live with regret over a leap you skipped for no good reason. I asked him if going for it is a skill. He said yes, and that it gets easier the more you do it.

The Move Before the Move

Every time Billy flipped, he did the thinking first. When he wondered what he’d even do besides coach, he made a simple list of things he liked: teaching, music, writing, yoga, mindfulness. Later he did a “mind dump” with three columns: things you want to do, things you need to do, things you want to accomplish. You pick what stands out and take one immediate action. Serving veterans stood out, so he called local veterans’ homes and offered to teach mindfulness for free. One of them asked if he could start the following week.

Once he decided, the moves came fast. He was set on starting his own nonprofit until a podcast guest gave a different piece of advice: join someone already doing the work. He called Prison Yoga Project to ask about Los Angeles, and he hung up as their LA director. The call lasted about a minute. When Give a Beat interviewed him to teach DJing, he told them they had better-credentialed people on their roster, and they hired him on the spot.

🔄 The Flipped Story Recipe Book

Every episode of The Flipped Story adds a recipe to the book. Billy didn’t give us one recipe. He gave us a sampler, five ingredients from someone who has rebuilt his life more than once, all built on one core: belief.

The Flipped Story Recipe Book card for Billy Bannon: key ingredient Belief, plus a five-ingredient sampler

Learn More & Connect with Billy

Reach Billy at billybannon@gmail.com or find him on Facebook as Billy Bannon. Learn about the work he does inside at Give a Beat and Prison Yoga Project.

Catch the full video interview!

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