10/26/2026
Over the weekend, DM Wooster and I met a man "JR" and his little pup, Warner, who had run out of gas on a busy road surrounded by Saturday afternoon tourists, multimillion-dollar vineyards and high-end wineries.
I was sure someone would pull over to help. We were already late for an appointment.
His old minivan was barely off the road, its hazard lights faintly blinking.
Cars kept passing. Duncan and I looked at each other and knew we needed to turn around.
We’ve been there, too. Not so long ago, we were the ones who needed help. Some people stopped. Others kept driving. You remember both.
I learned from my dad a long time ago that when it’s safe to stop and help, you do. Duncan and I have always been on the same page about this. You never know what someone is going through—or whether stopping could be one the thing that gives them a little faith back in the world - or in our case- saved us from a difficult situation.
On the ride to the gas station, he shared a little of his story. He’s worked his way back from living on the streets, earned a certificate in small-engine repair, and is working to build a business repairing generators, motorcycles, and other small engines. He was also a proud pup papa-- you could tell his little rescue dog had gotten him through some hard times.
We went to get him two gallons of gas, but after talking with him, that didn’t feel like enough. Duncan had some birthday money tucked away in his wallet, and we decided this was the best place for it.
He gave me this beautiful gift in return. ❤️
I keep thinking about the fact that, amid the daily work of getting back on his feet, he found the quiet time to create something beautiful.
As a career ownership coach, I spend a lot of time talking with people about what they want to build and the courage it takes to begin. This weekend, I was reminded that entrepreneurship doesn’t always look like the polished stories we see on LinkedIn.
Sometimes it’s earning a certificate. Putting a skill to work. Finding the courage to tell someone what you do and ask for an opportunity.
His story is his own, and there’s much more to it than one roadside conversation. But I’m grateful we stopped long enough to meet him.
If you’re local and need small-engine repairs, please reach out for his contact information.
Sometimes supporting our neighbors is as simple as giving someone a chance to put their skills to work. I’d love to see our community help him build on everything he’s worked so hard to begin.❤️
