The Constellation of Adaptability: Leadership Lessons from Veterans Who Shaped My Path
November 11, 2025
What if the greatest lesson from military service isn’t discipline — but adaptability?
Discipline got us through the gates at West Point. It carried us through ruck marches, pre-dawn formations, and the relentless cadence of military life. But in Afghanistan and Iraq, where chaos reigned and no plan survived first contact, it was adaptability that kept our teams alive and effective.
The ability to shift course, rethink assumptions, and adjust to reality in real time — that was the difference between success and failure. Discipline kept us ready. Adaptability kept us moving.
That same lesson guides me now as CEO of Madden Media. We’re a 300-person creative agency navigating remote collaboration, emerging technology, and a world still reshaping itself. Leading today isn’t about enforcing rules; it’s about fostering agility through trust, clarity, and purpose.
This Veterans Day, I’m reflecting on the constellation of mentors who forged those principles in me. Each modeled a lesson that continues to guide how I lead and how our team shows up for one another and the communities we serve.
Pillar 1: TRUST — The Foundation of Agility
Trust isn’t a soft skill; it’s the currency of agility. It’s what makes any high-performing team possible.
COL(R) William Ostlund — Trust Is Spherical, Not Linear
“Trust should not be viewed as a linear construct, and certainly not one in which trust flows predominantly in one direction. Rather, it must be treated as a spherical construct, in which the Army values, along with trust, are demonstrated fully and uniformly throughout the service, trust flows not only up the chain but down as well, and both are spread laterally to peers and adjacent units.”
William Ostlund
Ostlund was my sponsor at West Point. A fellow Nebraskan, a Ranger, and one of the first leaders who modeled integrity and leadership in action. His Command Philosophy from his Company Command days became one of the most formative documents of my career. It still shapes how I think about leadership today.
Ostlund taught that trust isn’t granted by rank; it’s earned through consistency and shared confidence. It moves in every direction — up, down, and sideways — and only grows when people see words and actions align.
What it means today: At Madden, trust is our operating system. It’s how our team stays aligned across disciplines and time zones. It’s how creative freedom and accountability coexist — the push and pull that turns collaboration into craft.
BG(R) Michael Meese — Get the Right People, Then Trust Them
“The key is to get the right people, train and empower them, and then let them achieve tremendous results.”
Michael Meese
He taught me that once you’ve vetted your team, your job isn’t to micromanage them. It’s to enable them. This means clearing obstacles, whether professional or personal. Understanding that your people’s personal stressors (financial or otherwise) are as real as their professional challenges and if a leader has these stressors it is damaging for morale and contagious. At West Point, as Deputy Head of SOSH, he showed me how empathy, humor, and readiness go hand in hand. He taught me that leaders don’t have to take themselves too seriously to take their people seriously – a lesson that directly shapes our culture today.
What it means today: We hire for character and skill, and then we trust our people to deliver. That trust is what allows for humor and humanity. It lowers the walls of hierarchy, sparks curiosity, and lets our teams build the collaborative relationships necessary to solve complex creative problems. Trust isn’t just about feeling good; it’s about giving talented people the room to do their best work.
Pillar 2: CLARITY — The Engine of Resilience
“Resilience isn’t just about bouncing back. It’s about bouncing forward.”
Jen Easterly
Jen Easterly taught me that resilience is an offensive mindset, and it’s built on clarity. I first met her at West Point, and later had the privilege of supporting her as she built the Army’s first Network Warfare Battalion. I watched her lead a new kind of organization operating in technical, legal, and political gray zones.
Her leadership was a blueprint: give smart people structure, clarity on the mission, and then the freedom to execute. She didn’t wait for permission to innovate; she designed systems that encouraged it and shaped how I think about modern teams.
What it means today: Disruption is opportunity. As AI reshapes our industry, clear intent allows our teams to evolve confidently. Structure creates safety; clarity creates speed. Adaptability thrives at that intersection.
🤝 Guy Filippelli — Adaptability Through Alignment
“Investing in tremendous teams and helping them dominate.”
Guy Fillippelli
If Jen Easterly taught me how clarity fuels a team’s resilience, Guy Filippelli showed me how it empowers their execution.
As a fellow veteran and the first CEO I worked for after the Army, Guy translated mission-focused principles into a fast-moving entrepreneurial environment. His philosophy was simple: a team can’t ‘dominate’ if they aren’t aligned. You can’t have alignment without empowerment. And you can’t have empowerment without clarity.
He gathered diverse thinkers, stripped away bureaucracy, and trusted small teams with big problems. Clear goals, bold intent, and space to execute that’s how you “dominate” in complex environments.
What it means today: At Madden, we practice this daily. In a remote environment, clear alignment is our mechanism for agility. It’s not just about a shared mission; it’s about clear briefs, defined roles, and transparent goals. When every person knows exactly what ‘winning’ looks like for their part of the project, the entire organization can pivot quickly, creatively, and confidently without waiting for top-down direction.
Pillar 3: PURPOSE — The Anchor that Keeps us Adaptive
Purpose isn’t a static “why”—it’s the moral and motivational compass that keeps you adaptable when plans fail and uncertainty reigns. In the military’s “fog,” purpose drove bold flexibility; today, it anchors our ability to pivot amid AI shifts and team challenges.
🗣️ LTC(R) Paul Yingling — Moral Courage For Bold Flexibility
“Officers conditioned to conformity in peacetime cannot be expected to behave boldly and flexibly in combat.”
Paul Yingling
Yingling’s essay A Failure in Generalship hit me hard after Iraq and Afghanistan. It wasn’t just a critique of leadership. It was a warning: when institutions punish dissent, they crush adaptability. His call for moral courage reminded me that change only works when rooted in truth.
What it means today: At Madden, adaptability must be honest. Sometimes that means questioning the brief, challenging assumptions, or telling clients the harder truth — that the most effective story isn’t always the easiest sell. Real adaptability takes moral courage.
❤️ Mike Erwin — Lead Yourself for Resilient Purpose
“Solitude strengthens people’s character—and their ability to lead with clarity, balance and conviction.”
Mike Erwin
Mike and I were classmates at West Point, and his journey from Army officer to founder of Team RWB continues to shape how I lead. When he spoke to our team at MUSE, he reminded us that adaptability isn’t frantic reaction; it’s calm responsiveness. You can’t adjust to change if you’re not anchored in purpose.
What it means today: Mike Erwin reminds me that adaptability starts within. Stillness builds clarity, and clarity drives confident action. In a world obsessed with speed, reflection is our competitive advantage. It keeps us adaptive without losing direction.
The Constellation That Guides Us
Service doesn’t end when the uniform comes off: it evolves. Discipline got us to the starting line. Adaptability is what keeps us moving forward.
And the constellation of trust, clarity, and purpose keeps us aimed toward what matters most.
At Madden Media, I see their influence in the way we work together:
- Trust gives our teams the safety to take creative risks.
- Clarity keeps us aligned and allows us to move fast.
- Purpose grounds us in why we do the work and create lasting impact.
The military taught me to lead through uncertainty. But this team — creative, compassionate, and courageous — reminds me every day that leadership is still a form of service.
And of course to all of those other veterans and leaders who shaped my path. Both the ones that taught me who not to be (they will remain unnamed) and to those who taught me other things that did not make this article. So many of you are part of who I am today as a leader, father, husband, and global citizen. The stories and the lessons are some of my dearest memories.
To all veterans: thank you for your service.
To everyone leading a team, a family, or a community may you find your own constellation of mentors to light the way.
