Earn Your Spurs

September 19, 2026

I’ve been thinking a lot lately about what it means to earn your spurs.

Maybe that’s inevitable when you buy a ranch in your fifties after spending nearly 30 years doing something completely different. I own a ranch. I own horses and cattle. I spend more time than I ever imagined thinking about grass, fences, equipment, water, and things that can break. But if you put me in a room with someone who has spent 40 years raising cattle, I’m probably going to do a whole lot more listening than talking.

I may own the ranch, but I’m still earning my spurs.

There is something about that idea that extends well beyond ranching. We live in a world where it has become remarkably easy to declare ourselves something. We choose our titles. We write our own bios. We build our personal brands. We can call ourselves experts, thought leaders, strategists, founders, executives, or just about anything else that fits neatly into a LinkedIn headline.

But some things still have to be earned. You earn them by doing the work. By sitting in the chair. By making decisions when the answer isn’t obvious. By getting some of those decisions right and getting others spectacularly wrong. By owning a number, leading people, building something, and living with the consequences long enough to understand the difference between a good idea and a good idea that can actually work.

There aren’t many shortcuts to that kind of experience.

I’ve been fortunate to sit in a lot of different chairs during my career. I’ve been a teacher, principal, district chief technology officer, an educational technology chief strategy officer, chief marketing officer, sales leader, executive, and CEO. I’ve managed teams, owned P&Ls, helped build businesses, and been part of organizations experiencing significant growth. I don’t say any of that because I think I’ve reached some mountaintop. Quite the opposite.

The older I get, the less convinced I am that you ever completely earn your spurs. Because the spurs you earn have a shelf life.

I was a chief technology officer in a school district. That experience still matters. I understand what it feels like to sit in that chair, make those decisions, and be accountable for them. But I did that job in a different era. A school district technology leader in 2026 is dealing with challenges I never encountered. If I walked into a room today and acted as though my experience gave me all the answers to their problems, I wouldn’t be demonstrating credibility. I’d probably be diminishing it.

Some of my other experiences are much more fresh. I’ve recently sat in executive chairs, owned a P&L, built go-to-market strategies, led teams, and been accountable for growth. I’ve watched strategies translate into measurable results. Those experiences carry weight, but they still don’t give me a lifetime pass to stop learning.

Maybe that’s the strange bargain that comes with experience. You’ve earned the right to trust some of your instincts, but not the right to stop questioning them.

After enough years doing something, you begin recognizing patterns. You’ve seen certain things before. Someone describes a problem and sometimes you can see where it is headed long before everyone else does. You see around corners not because you’re smarter than the people in the room, but because you’ve watched a similar story unfold somewhere else.

I’ve had moments over the years where an idea I raised didn’t get much traction. Months later, sometimes much later, circumstances changed and essentially the same idea resurfaced. Occasionally someone has even looked at me and said, “You told us this was going to happen.”

I’d love to say my reaction is always some enlightened version of, “That’s okay. I’m just glad we got there.”

Sometimes it is. Sometimes it’s also, “Well, damn.”

That creates a tension I don’t think we talk about enough. What do you do when you believe your experience is showing you something the room isn’t ready to see? You can stomp your feet. You can remind everyone of your résumé. You can run the idea up the flagpole until somebody finally listens. You can pull out your spurs and make sure everybody knows you earned them.

That’s never really been my style. But I’m beginning to wonder whether there are times when humility can drift too far toward passivity. If experience has taught you something that could help an organization avoid a mistake, do you have some responsibility to push harder? And if the room isn’t receptive, how many times do you keep offering the same perspective before you let experience run its course?

I don’t have a perfect answer to that.

What I do know is that I don’t want experience to turn into entitlement. I don’t want to become the guy saying, “I’ve been doing this for 30 years, so trust me.” There are plenty of people with far less experience than I have who know things I don’t know. Different backgrounds, generations, industries, and experiences make strategies richer. Some of the best ideas I’ve ever been part of became better because somebody challenged what I originally thought we should do.

That’s what I want. Debate the idea. Tear it apart. Bring a perspective I haven’t considered. Tell me where my experience is outdated. Show me the flaw in my thinking. Blend what I’ve learned with what you’ve learned, and maybe we end up somewhere neither of us would have reached alone.

But engage with it.

There’s a difference between challenging an idea and dismissing it. There’s also a difference between respecting experience and blindly deferring to it. The best organizations I’ve been part of somehow find room for both experience and curiosity.

Maybe that’s what earning your spurs really means. It isn’t collecting enough titles that people finally have to listen to you. It isn’t reaching a point where your instincts are beyond question. And it certainly isn’t declaring yourself an expert and expecting everyone else to accept the label.

It’s doing enough real work that you’ve earned some pattern recognition. It’s producing results that give your ideas credibility. It’s making enough mistakes that you have some humility about those ideas. And then it’s continuing to learn quickly enough that yesterday’s experience doesn’t become tomorrow’s blind spot.

I’m learning that lesson all over again at Halcyon Ranch. In the education and technology world, I’ve earned a few spurs. On this ranch, I’ve been at it for about a year. I have a tremendous amount to learn, and I’m surrounded by people who know things about cattle, horses, land, and agriculture that I don’t.

So I listen. I ask questions. I bring the things I do know to the table, and I try not to pretend I know the things I don’t.

Maybe that’s not a bad way to approach the boardroom either.

After nearly 30 years, I hope I’ve earned enough experience to have something useful to contribute. I also hope I never become so enamored with that experience that I stop being curious about what someone else can teach me.

I don’t need to win the room. I just want the room to think, and also I do not even own a pair of spurs…

At least not yet!