What 18 Issues of Halcyon Headwinds Taught Me

May 30, 2026

“Some of the best lessons are learned under a wide Texas sky.” ~ Texas proverb

When I started Halcyon Headwinds in January, I honestly did not know exactly what it would become. At first, it was simply a way to slow down and reflect a little. After 30 years in education and nearly two decades in the private sector, you accumulate a lot of experiences, successes, failures, and perspectives. I think part of me just wanted a place to process some of that out loud.

What surprised me most was not necessarily the growth of the newsletter itself, though crossing more than 840 subscribers has been incredibly humbling. What surprised me most was how often the same themes kept resurfacing no matter what topic I was writing about. Whether I was writing about EdTech strategy, leadership, AI, cybersecurity, trust, fatherhood, music, ranch life, or business growth, the lessons kept circling back to the same handful of ideas. Maybe that is what experience actually is. Not constantly discovering new truths, but rediscovering the same ones from different angles until they finally become part of who you are.

So before jumping into the next chapter of Halcyon Headwinds, I thought it might be worth reflecting on a few things these first eighteen issues reinforced for me.

If there is one idea underneath almost every issue I have written, it is trust. Trust in leadership. Trust in teams. Trust in products. Trust in relationships. Trust in yourself. In EdTech especially, there is constant pressure to move faster. Faster product launches. Faster growth. Faster AI adoption. Faster sales cycles. But schools do not operate on startup timelines. They operate on relationship timelines.

District leaders are responsible for students, teachers, communities, school boards, and taxpayer dollars. That naturally creates caution, and honestly, it should. One of the biggest mistakes companies make is trying to force sales velocity before trust velocity exists. Momentum built without trust usually breaks under pressure eventually. Ranch life reinforced the same lesson for me. You cannot force trust with horses. You build it slowly through consistency, patience, and repetition. Turns out leadership works pretty similarly.

Another theme that kept resurfacing was how the best companies during difficult seasons usually stay closest to their mission. The current EdTech market feels heavy right now between AI disruption, cybersecurity concerns, screen time debates, budget pressure, investor pressure, and market uncertainty. When markets tighten, companies often feel pressure to become something different overnight. They start reacting instead of building. They chase competitors. They launch too many things. They swing for home runs on every pitch.

What these first eighteen issues reinforced for me is that the companies that survive downturns are rarely the ones making the wildest moves. Usually, they are the ones staying disciplined enough to remain close to their mission while everybody else is panicking. In a lot of ways, it reminds me of investing. Experienced investors usually do not abandon the market emotionally during downturns. Historically, the people who stay disciplined and consistent tend to win over the long run. I think EdTech works similarly. The organizations that continue listening to customers, improving thoughtfully, and staying grounded in why they exist usually emerge stronger once the market stabilizes.

Ranch life also keeps reinforcing for me that foundations matter more than momentum. Weak fences fail under pressure. Poor water systems eventually create problems. Rushed foundations rarely stay hidden forever. Organizations are not much different. You can manufacture momentum for a while through aggressive growth, marketing, hiring, or hype. But if the operational foundation underneath it is weak, eventually the cracks show up. The organizations that endure are rarely the loudest. Usually, they are the ones quietly strengthening the foundation while everyone else is focused on appearances.

One topic I have written about several times is the idea that mission and margin are not enemies. For a long time, many educators struggled with the idea of entering the private sector because they felt like they were somehow leaving the mission behind. I wrestled with that too when I first left public education. Over time, though, I realized mission driven work absolutely exists inside for profit organizations. Some of the most impactful work I have ever been part of happened inside companies helping schools modernize infrastructure, expand access to technology, strengthen family engagement, and improve communication for millions of students and families.

Revenue does not eliminate the mission. What matters is whether leadership protects the mission when pressure shows up. That balance is hard. Markets create pressure. Boards create pressure. Investors create pressure. But I still believe organizations can pursue growth and maintain integrity at the same time.

Over the years, I have worked around some incredible superintendents, principals, CEOs, coaches, and operators. One thing the best ones consistently had in common was this: they knew how to bring people back to center. When everybody else was panicking, reacting emotionally, or getting distracted by noise, great leaders had a way of calmly reminding the organization why it existed in the first place. That does not mean they ignored problems or avoided accountability. It just means they understand panic rarely improves decision making. Anybody can lead when things are easy. Steady leadership matters when things are hard.

Another lesson that became more obvious to me while writing this newsletter is that the loudest voices are not always the wisest. Social media rewards speed. Algorithms reward outrage. Hot takes travel fast. Depth usually moves slower. One thing I have realized watching a lot of EdTech discourse recently is that the people with the strongest opinions sometimes have the least operational context. That does not make them bad people. Everybody deserves an opinion. But there is a difference between commentary and responsibility.

It is easy to criticize systems you have never had to operate. It is harder to sit in a room at three in the morning with your technology team trying to stabilize systems for students and teachers during a crisis. Experience changes perspective. One thing I hope this newsletter continues to reinforce is that accountability and empathy can exist together. Those things are not opposites.

This newsletter also forced me to think more honestly about balance. For most of my career, I probably treated rest as something you earned after the work was finished. The problem is the work is never finished. There is always another initiative, another meeting, another trip, another goal, another problem to solve. Writing about ranch life, music, fatherhood, and leadership forced me to think more honestly about sustainability. You cannot lead well exhausted forever. You cannot think clearly exhausted forever. You cannot build meaningful relationships exhausted forever. Some of the clearest thinking I have done this year happened after stepping away long enough to breathe a little.

After eighteen issues, the simplest and probably most important lesson underneath all of them is this: leadership is still about relationships. Technology changes. Markets change. AI changes. Strategies change. Relationships still matter most. The best leaders I have worked around understood relationships. The best principals understood relationships. The best coaches understood relationships. The best parents understand relationships.

Trust is relational. Leadership is relational. The mission is relational. At the end of the day, people remember how consistently you showed up long after they forget most presentations, meetings, or product launches. That may be the biggest thing these first eighteen issues reinforced for me.

At the end of the day, the work is still about people.

I appreciate everybody who has followed along so far.

There is a lot more coming.

See you in Issue 20.