Wiser Now

April 25, 2026

“I’m not broken, I’m just wiser now.” - Chad Stevens

Many folks in my network know I love live music! I have been at the Larry Joe Taylor Music Festival here in Stephenville the last few nights. After tonight I will cross 50+ live shows in 2026 already. What many don’t know is I also enjoy playing, songwriting and I recently started up again. I have written about 10 new songs in the past year.

I’ve been spending some time at Double D BBQ lately. It’s close to home, and like a lot of good places, there’s a story behind it. First, it has been voted one of the best music venues in Texas. Then I actually met the owner down in Key West at the Mile Zero Music Festival back in January, just by happenstance. He’s building something as a small business owner, trying to make it work, and you can feel that when you walk through the gate. It’s real.

The crowd and the singers are a mix of people. You’ve got guys and gals in their late 20s, and then you’ve got people in their 70s and 80s still getting up there and playing. What stands out more than anything is how supportive everyone is of each other. It’s a community.

I’ve played there three times now, but the last couple sets were different because I worked a few original songs into the set. When you play covers, you’re playing something proven. It’s familiar. People recognize it, especially at a place like Double D’s where Texas music is part of the culture and people know what they came to hear.

But when you tell a crowd that this next song is something you wrote, everything changes. You can feel it. People lean in. And for me, that’s a level of vulnerability that doesn’t show up in many other parts of life. I get nervous, because there’s nothing more personal than creating something and putting it out there. It’s completely different from most of what I do day to day, but I’ve found that it creates balance.

What stood out the first time I played originals was what happened after. People came up and told me they enjoyed it, and in that moment you realize you created something that connected with someone, even if just for a few minutes. You may never see them again, but you gave them something. That’s a pretty cool feeling.

In my day-to-day work life, everything is measured. KPIs, pipeline, forecasts. There’s a scoreboard, and you’re constantly trying to understand what’s working and what’s not. When you’re up on stage, there isn’t. The first night I played, I think I made five dollars in tips and got a free beer, and honestly that felt like a win. That’s a very different mindset.

When you’re writing or playing music, it’s not about metrics. It’s about feeling. You’re tapping into a different part of your brain. What I didn’t expect is how much that would carry back into everything else. It’s made me a better leader.

Because when you put something out there that’s personal, you learn how to be vulnerable. You learn how to be honest in a different way. I think the best leaders have that balance. They’re willing to be real, and that’s what builds trust. That’s what develops other leaders.

There’s also something else I didn’t expect. Music helped me through a pretty significant life transition. In a lot of ways, this part of me had been sitting dormant for 30 years. I played when I was first out of college a lot at the Old Quarter Acoustic Cafe in Galveston back when I was a young teacher, and we even had an administrator parody band back at Clear Creek ISD, Burnt Toast. It was fun, but life moves fast, and somewhere along the way it just faded into the background.

It’s a little crazy to think it took 30 years to come back to it, and even longer to be comfortable enough to put it out there. But I’m glad I did. I’ve even taken a few songs and had them mastered, which pushed me to take it more seriously and practice more. That’s been one of the unexpected benefits. Once you put something out into the world, it raises your own standard. There are a lot of positive byproducts of just deciding to try.

At this stage in life, you start to realize something. You’ve got fewer days ahead than you’ve already lived, and that changes how you think about things. Some things are just worth doing.

That’s part of why I started Halcyon Headwinds. After 30 years in education and education technology, I’ve been fortunate to learn a lot along the way. It would be a shame not to share that, not just for those building and leading education companies, which matters for the future of our students, but for anyone trying to figure things out along the way.

In a lot of ways, it’s not that different from what I’ve experienced at Double D’s. It’s a community. People sharing ideas, supporting each other, and putting themselves out there. Writing, just like music, is another way of doing that. It’s not something that has always come naturally to me, but it’s something I’ve come to believe is important.

For me, the takeaway is pretty simple. I think everyone has something inside of them they want to explore, but most people don’t do it because they’re worried about being judged. I get that.

I’m not a trained musician. I don’t read music. I taught myself guitar in college, and over the past year I’ve written several songs. I’m probably averaging one a month. I don’t say that because I think they’re perfect. I say it because I decided to try.

There’s something powerful about turning a feeling into something real and then putting it out there. It’s an outlet, and honestly it’s healthy. When you’re under pressure, constantly chasing outcomes, it’s important to have something that pulls you out of that world.

It doesn’t have to be music, but it should be something. Because if it brings you joy, it’s worth making time for.