What a Navy SEAL and astronaut can teach us all about leadership, risk, and staying grounded

Every so often, a conversation comes along that lingers, not because of a single story or accomplishment, but because of the character behind it. That’s how I felt after watching Captain Chris Cassidy on the Walker Webcast.

Chris is one of only a handful of individuals to have served both as a Navy SEAL and as a NASA astronaut. He’s logged nearly a year in space, led SEAL teams in combat, and now heads the Medal of Honor Museum and Foundation. But titles don’t capture what makes him compelling. It’s how he reflects on adversity, leads with humility, and distills extreme experiences into remarkably grounded lessons that stayed with me long after we stopped recording.

Here are a few reflections from that Walker Webcast conversation that I’ve been thinking about ever since.

Preparation as the antidote to fear

Chris said something simple, but profound: Fear is often just a response to uncertainty. The best way to reduce uncertainty is through preparation.

That struck me. Whether you're launching into space or navigating volatile financial markets, fear creeps in when you're unsure what’s around the corner. Chris described how SEALs and astronauts alike prepare for the “next worst failure.” At NASA, they even rehearse the failure after the failure just to be ready. That level of discipline improves outcomes and creates calm in chaos.

It made me think about how our team at Walker & Dunlop approaches risk. The smartest professionals I know aren’t fearless; they’re obsessively prepared. It’s not courage that pushes them forward; it’s the confidence born of rigorous thought and planning.

Quiet leadership matters more than ever

Willy asked Chris about how many SEALs have a quiet, steady approach to leadership. No grandstanding. No barking orders. Just consistency, presence, and showing up ready every time.

Chris talked about always being five minutes early, gear squared away, and ready to move. That behavior wasn’t flashy, but it created stability. His team followed suit because they trusted him, not because he told them to, but because he showed them how.

In an era where leadership is often confused with visibility or charisma, Chris’s example was a reminder that composure, consistency, and a deep sense of responsibility can be just as powerful, especially in high-stakes environments.

Embracing transitions—and becoming the new guy again

Chris didn’t leave the SEALs because he was done with it. He left because he was curious. Becoming an astronaut meant starting over. Suddenly, he was the “new guy,” learning how to navigate spacecraft systems, perform spacewalks, and deliver talks to schoolkids—all things he hadn’t done before.

There’s something incredibly valuable in becoming a beginner again. It keeps you humble. It forces you to listen. It renews your sense of growth.

It also reminded me of how quickly industries evolve. Real estate, finance, and even leadership itself all shift constantly. The people who thrive aren’t always the ones with the most tenure. They're the ones who are willing to retool, relearn, and re-engage.

Legacy isn’t a buzzword; it’s a responsibility

Today, Chris leads the Medal of Honor Museum, a project with both national and deeply personal significance. What struck me most wasn’t the size of the capital campaign (though raising $285 million is no small feat). It was how clearly Chris understood the mission. This is about preserving the stories of extraordinary sacrifice so future generations can understand what service truly looks like.

The museum isn’t about glorifying war. It’s about honoring courage. It’s a reminder that values like integrity, loyalty, and service above self still matter and deserve to be preserved.

It made me reflect on how we think about legacy at Walker & Dunlop. Yes, we aim to be the best in our industry. But what do we stand for beyond that? What are we building that will last? Chris’s work is a powerful example of aligning leadership with meaning.

Anyone in a leadership role would highly enjoy and benefit from watching this special episode of the Walker Webcast. Check out this incredible episode.