On community, finding your people, and making room for others.
“Some relationships are built around convenience. Others are built around connection. You don't always know the difference until life gets a little complicated.”
— Chad Stevens
Back at ISTE 2026, I had the opportunity to sit down with my longtime friend Diane Doersch for an episode of her Beneath the Water podcast. The episode was released on October 27, and listening back to our conversation reminded me just how much ground we covered. We talked about my journey from classroom teacher to education executive, some lessons learned along the way, fishing stories, and even my questionable mustache. But one thing kept coming up throughout the conversation. Community.
Diane is building something pretty special with Beneath the Water. It's more than a podcast. Her vision is to create a community where people can connect, learn from one another, find mentors, and have meaningful conversations without the barriers that sometimes exist in traditional professional networks. After joining her community watch party a few weeks ago, I found myself thinking about how important that work really is and how much my own understanding of community has changed over the years.
The Difference Between a Network and a Community
I've spent 30 years working in education and technology. Along the way, I've met thousands of people, worked at some incredible organizations, and built a pretty extensive professional network. But I've learned there's a big difference between knowing a lot of people and having meaningful relationships.
The strongest professional friendships I've developed are the ones where we've gotten to know each other beyond our titles. We know about each other's families, understand what makes one another tick, and have been through some difficult situations together. We've had hard conversations. We've disagreed. We've supported each other. Sometimes we've even cried together, shared things that made us vulnerable, and trusted one another with parts of our lives that don't show up on a résumé or LinkedIn profile. Those experiences build something that a LinkedIn connection never will.
During the podcast, Diane asked what advice I'd give aspiring leaders. One of my answers was pretty simple.
Build the relationships before you need them.
We live in a world where too many relationships are transactional. We connect with people because they might help us get a job, close a deal, or accomplish something professionally. There's nothing wrong with building a network, but if the only reason you're developing a relationship is because you need something from someone, you're missing the point. Real relationships are built long before you know whether you'll ever need them. And sometimes you don't fully appreciate their value until life gets complicated.
Over the past couple of years, I've experienced some significant changes in my own life. Through those experiences, I've learned a lot about friendship and the people I can genuinely count on. Some relationships turned out to be more about convenience than connection. But something pretty remarkable happened, too. The more open I've become about my life and the things that matter to me, the more people have leaned in. Some of those relationships have grown stronger than I ever expected.
I've found myself surrounded by a growing group of people who ask the hard questions, care enough to understand what's really going on, and show up when it matters. As Tracy Lawrence reminded us years ago, you find out who your friends are. And I'm increasingly grateful for mine.
Making the Table Bigger
Diane and I first really got to know each other while serving together on the CoSN Board of Directors. We'd crossed paths professionally before that, but working together gave us the opportunity to build a genuine friendship. Over six years, we helped navigate some significant organizational changes. We had a big vision for what CoSN could become, and part of that meant thinking carefully about what the next generation of district technology leaders would look like.
Who would be leading technology in our schools ten or twenty years from now? Were we creating opportunities for those leaders to participate? And were we making sure enough different perspectives were represented in the conversations shaping the future of education?
I'm proud of the work we did alongside so many dedicated board members and leaders. Today, when I look around CoSN events, I see more women, more leaders of color, more emerging leaders, and a broader range of perspectives represented in the room. That didn't happen by accident. It required intentional leadership, difficult conversations, and a willingness to challenge the way things had always been done.
Diane helped lead us through some incredibly important transitions, and I've always appreciated her ability to bring people together, even when the conversations weren't easy. During our podcast conversation, she described that work as building a bigger table. I think that's exactly right.
Great communities don't just make room for more people. They become better because of the people they invite in.
And that's what I see Diane continuing to do today.
A Place Where Everyone Can Learn
One of the things that struck me during the Beneath the Water community watch party was Diane's vision for creating a space with a low barrier to entry. Too often, participation in professional communities revolves around titles, organizational status, conference attendance, or who happens to know whom. And let's not forget the financial barriers. Conference registrations, travel expenses, association memberships, and professional development opportunities can cost thousands of dollars. For educators and emerging leaders, those costs can make participation difficult or even impossible.
But imagine a community where someone with 30 years of experience can have a meaningful conversation with a teacher who's just beginning a career in education technology. Where both people feel comfortable asking questions, neither feels the need to prove they belong, and the opportunity to participate isn't determined by a job title or the size of a professional development budget. Where people can be honest about the things they're struggling with, learn from one another, and develop relationships that extend beyond a single event.
That's incredibly valuable, and it's something I believe our industry needs more of.
Diane has always been a natural connector. Throughout the years I've known her, she's consistently worked to make the table bigger, the room more inclusive, and the conversations smarter. She's also someone who understands that mentorship and sponsorship aren't just about offering advice. They're about advocating for people, creating opportunities, and helping others develop the confidence to take their next step. I can't think of many people better equipped to build the kind of community she's envisioning.
And while Beneath the Water is still relatively new, I think she's onto something important.
Getting Comfortable Being Yourself
Another part of our conversation got a little more personal. Diane asked about the changes I've experienced over the past year and what I've learned along the way. I told her that, at 54, I've finally gotten pretty comfortable just being Chad. Boots, pearl snap shirts, a questionable mustache, and all.
For much of my career, I probably spent more time than I'd like to admit trying to fit some version of what I thought a successful executive or education leader was supposed to be. But after 30 years, I've had the opportunity to look back at the things my teams and I have built. Some of those accomplishments have lasted. Some have made a meaningful difference for educators and students. And I've come to appreciate that the work can stand on its own. I don't need to spend nearly as much time worrying about whether I fit somebody else's expectations.
Moving back to Texas and building Halcyon Ranch reinforced that lesson. Buying a ranch and starting a new chapter of life required a pretty significant bet on myself. There was plenty I didn't know, and there's still a lot I'm figuring out. But it also gave me an opportunity to think about what I genuinely enjoy, what matters to me, and the kind of life I want to build.
And I've noticed something interesting.
The more authentic I've become, the better my life has gotten. And the better my relationships have gotten.
I'm not sure anyone ever completely conquers imposter syndrome. But there's something liberating about reaching a point where you're comfortable being yourself, even when that version of you doesn't fit everyone else's expectations. Not everyone is going to understand every choice you make, and that's okay. The people who matter will take the time to get to know you. And those are the people worth building a community around.
Community Requires Showing Up
One of the things I've enjoyed most about moving back to Texas and building the ranch is getting to know people in a different way. I've reconnected with old friends, developed new relationships, and learned an awful lot from people who know considerably more about ranching than I do. Which, admittedly, is a pretty long list.
But I've also been thinking about how I can continue contributing to the education and technology community that's been such a big part of my life. That's one of the reasons I started Halcyon Headwinds. What began as a way to share a few reflections on leadership, business, and life has grown into a community of more than 870 subscribers. I still find that pretty remarkable.
My intention has always been to keep these Saturday morning reflections free and accessible. I'm not trying to build another professional association or create some elaborate business around a newsletter. I just want to share what I've learned. Hopefully, something I've experienced can help another leader make a better decision, navigate a difficult situation, or find the confidence to bet on themselves. And maybe, somewhere along the way, I'll learn a few things from the people reading it.
That's the beauty of community. It works in both directions.
During Diane's watch party, I noticed a few familiar faces. People I've known for years who I didn't even realize were participating in her community. It reminded me that these relationships don't have to exist in separate worlds. The people we know through our careers, our communities, our families, and our personal interests often have more in common than we realize.
But building those connections requires something from us. We have to show up, participate, share what we know, and remain curious about what others can teach us.
Community isn't something we join and expect to serve us. It's something we help build by showing up for one another.
Beneath the Water
I want to close by encouraging you to spend a little time exploring what Diane is building with Beneath the Water. Listen to the podcast, certainly. We had a great conversation, and I hope you'll enjoy it. But more importantly, take a look at the community she's creating around it.
Diane's vision goes well beyond producing interesting conversations. She's working to create a place where people can find mentors, develop meaningful relationships, and grow together. She's doing it with the same intentionality and commitment to inclusion that I watched her bring to our work at CoSN, and I think that's worth supporting.
I plan to spend more time participating myself. Not because I need another professional network, but because I believe in what she's building and want to contribute where I can.
As I get a little closer to whatever retirement eventually looks like, I've been thinking more about how to continue expanding my impact while making room for the things that matter most to me. Relationships are pretty high on that list. Maybe higher than they've ever been.
I've been fortunate to work with some remarkable people throughout my career. If sharing a few experiences, making an introduction, or offering some encouragement helps someone else along their journey, that's time well spent. And if I can help Diane build something that makes those opportunities available to more people, even better.
Because the longer I do this, the more convinced I become that the most meaningful measure of our success isn't how many people know our names.
It's how many people are better off because we took the time to know theirs.
Until next Saturday, keep your head up and your boots on the ground.
P.S. A special thanks to my friend Diane Doersch for the conversation and for the community she's building through Beneath the Water. If you're looking for a place to connect, learn, and grow alongside some great people, I encourage you to check it out. And if you listen to our conversation, I'd love to hear what resonates.
