What Lasts After the Bell Rings

August 15, 2026

“You rarely get to choose which lesson someone carries with them. Your job is to give them enough good ones to choose from.”

This week, I found myself scrolling through the subscriber list for Halcyon Headwinds. There are around 870 people on it now, and it is an interesting collection of people from nearly every chapter of my life. There are founders and CEOs, educators and technology leaders, current and former colleagues, friends, family, and people I have never met. But as I scrolled through the list, I started noticing some names that took me back almost thirty years. Former students.

The first one I noticed was Nicholas Buchanan. I was Nick’s assistant principal when he was in elementary school, and we got to know each other pretty well. Years later, when he was in high school, our paths crossed again when I was a district technology leader and he came out to our technology center and I did some mentor work with him. Today, he has built a successful career of his own, and from what I can see, he has also continued to find ways to pursue things that bring him joy. I love that. There is something pretty special about knowing someone as a kid, losing touch for stretches of time, and then getting to watch from a distance as he builds a life of his own.

Then there was Craig Liberty. I knew Craig when he was in elementary school and I was Coach Stevens. He recently commented on something I wrote about Capture the Golden Football, one of those ridiculous games we created that somehow became legendary to a bunch of elementary school kids. I had written about mowing the field myself to make the experience special. Craig remembered the game. He had no idea I had been the one mowing the field.

Years later, when I was working in Chicago, Craig’s mom reached out to tell me that he and several guys I had taught were coming to town for a Cubs game. I met them after work and bought them a few rounds of beer. They were grown men by then, starting careers and building lives of their own, but I remember how funny it felt because they still seemed almost amused that they were sitting in a bar drinking beer with Coach Stevens. At that point in my career, I had accumulated plenty of other titles, but none of those mattered to them. I was still Coach Stevens.

Then I saw Ben Muths. Ben reached out to me a while back because he was considering leaving public education and moving into education technology. We talked through the transition, and around the same time I happened to see that a former colleague had posted a business development opportunity. I made an introduction, and Ben got the job. I remember telling him afterward, “Just so we’re clear, this isn’t normally how this works.”

Since then, I’ve watched him continue to grow, take on bigger roles, exceed goals, win recognition, and build a really nice career. He has also continued running his barbecue business on the side, and apparently I have some free barbecue waiting for me the next time I make it down his way. Now that I’m back in Texas, I probably need to collect on that.

I’m incredibly proud of all three of these young men, but really, I’m proud of all my former students. I’ve been fortunate to watch some of them grow up, build careers, start families, and find their own paths. Others I’ve lost track of completely. Either way, I still think about those kids and wonder where life took them. I hope they know that the opportunity to be part of their lives, even for a short time, meant more to me than they probably realized then, or maybe even realize now.

Seeing those names made me think about the 23 or 24-year-old version of myself who first walked into an elementary school in 1996. I don’t think that guy could have imagined any of this. When you’re that age, you’re mostly living in the now. I wasn’t standing in the gym wondering what these elementary students would be doing thirty years later. I was trying to be a good teacher. I wanted kids to develop a lifelong love of being active. I wanted them to experience lots of different things. I wanted my classroom to be disciplined, but within that structure, I wanted us to have a hell of a lot of fun.

I also understood there was another responsibility that came with the job. For a period of time, I was the only male teacher on campus. Many of those kids had incredible families and great men in their lives. Some had more challenging situations. Either way, I understood that I had a unique opportunity, particularly with the young boys, to model what I thought being a good man looked like. Work hard. Treat people right. Have some fun. Take care of people.

At the time, I probably thought I was teaching kids. Looking back, those kids were teaching me too. That’s the part of teaching I don’t think we talk about enough. We spend so much time wondering what impact we’re having on students that we forget how much they are shaping us. Those kids taught me how to build culture. They taught me that people will work incredibly hard when they know you care about them. They taught me that discipline and joy aren’t opposites. In fact, some of the most joyful environments I’ve ever been part of also had incredibly high expectations. Most importantly, they helped me begin to understand what kind of life I wanted to build.

The interesting thing is that the desire to make an impact started even earlier for me. I can remember being in third grade in Mrs. Wood’s class at Best Brannen Elementary. I was a pretty good student then and a voracious reader. I would try to finish my work early so I could go down to a kindergarten classroom and help younger kids read. I was nine years old. I certainly didn’t have some grand career plan. I wasn’t thinking about leadership or scale or mission. I just knew there was something I loved about helping another person get better at something.

Somewhere along the way, that became the thread running through my career. I actually started college as a chemical engineering major. My dad was an incredible engineer, with degrees in chemical and electrical engineering, and following that path seemed to make sense. I have tremendous respect for engineers and the impact their work has on all of our lives. It just wasn’t the kind of impact I wanted to spend my life pursuing. I was drawn toward people.

At first, impact meant the kids standing in front of me. Then I started wondering what would happen if I could help create that same kind of culture across an entire school. Later, it became a district. Eventually, I moved into the private sector, where the things I helped build could reach schools and students I would never meet. For much of my career, I thought about impact in terms of scale. How can we help more people?

That has led to a career I’m incredibly grateful for. I’ve been fortunate to contribute to work that has touched millions of students, educators, and families. Some of those people may have benefited from something I helped build without ever knowing my name, and that’s exactly how it should be. Maybe a kid had better access to technology. Maybe another learned to code. Maybe a family became a little more connected to their child’s school. Most of that impact is impossible to measure, and I’ll never know the names attached to it.

Somewhere during the last couple of years, though, my definition of a successful career has started changing. For a long time, part of my motivation was proving I could do the next thing. Could I lead a school? Could I build something bigger? Could I become an executive? Could I run a company? Could I help scale something that mattered? Sometimes I chase those things for the right reasons. Sometimes, if I’m being fair to myself, I probably chased them for the wrong ones.

Today, the scoreboard looks different. I still care about building things that matter, and I’m not done doing that. But I’m increasingly convinced that some of the most meaningful impact of a career is the part you can never measure. You don’t know which student remembers something you said thirty years ago. You don’t know which employee took something they learned working with you and eventually used it to become a better leader. You don’t know which kid benefited because a school had better technology. You don’t know what someone did differently because of something you wrote. Most of the time, you never get to see the butterfly effect. Every once in a while, you get lucky enough to see three names on a subscriber list.

I learned this from the other direction too. When I was in high school, I had a coach named Jim Arthur. Coach Arthur was one of those people who had an impact on my life long after I stopped playing for him. He later helped me get back to my hometown to do my student teaching, but one of the things I remember most clearly happened much earlier. We were riding home from a baseball game one night when he told me something simple: “Chad, good things happen to good people.”

I’ve never forgotten it. I doubt Coach Arthur got off that bus thinking he had just delivered some profound life lesson that one of his players would still be talking about decades later. He was probably just talking to a kid on a bus. But that’s how impact works. You rarely know which moments stick, which is why you have to keep creating good ones.

Thirty years later, when I think about what I hope Nick, Craig, Ben, and all those other kids remember about our time together, it isn’t really a lesson from the curriculum. I hope they remember that we worked hard and had fun. I hope they remember that I cared. I hope somewhere along the way they learned that life is too short not to find some joy in it. I hope they build careers they enjoy, take care of their families, live with passion, and find opportunities to be that same kind of person for somebody else.

Mostly, though, I hope they know how much they gave back to me. Those kids helped shape the teacher I became. That teacher shaped the principal I became. Those experiences shaped the leader I became. And all of it continues to shape the person I’m trying to become today. The same is true of the employees, colleagues, coaches, mentors, customers, friends, and countless other people who have crossed my path over thirty years.

Maybe that’s what I misunderstood about impact for a while. I spent years trying to scale it, and there is nothing wrong with that. Helping a million people is an incredible opportunity. But impact doesn’t only move outward. Sometimes it circles back. Sometimes it shows up thirty years later in the name of someone who still remembers a game you played together in third grade. Sometimes it’s a former student asking for career advice. Sometimes it’s a group of grown men sitting in a Chicago bar who still see the young PE teacher they knew as kids.

I don’t need a former student reading this to call me or thank me, although I’d certainly love to hear from more of them. What I’d really love is for one of them to read this and think about somebody in front of them today. Maybe they’re coaching Little League. Maybe they’re teaching a classroom. Maybe they’re managing their first employee. Maybe they’re raising their own kids. Maybe there’s simply a young person somewhere in their life who could use another good adult in their corner.

Be that person. Coach Arthur probably didn’t know what I would do with something he said on a bus, and Coach Stevens certainly didn’t know where all those elementary school kids were headed. That’s the beautiful part. You don’t have to know where the investment will lead. You just have to care enough to make it.

Thirty years later, somebody might still be carrying it with them.