Forged in the Wilderness: Ian Perkins ’05 on Leadership and Service
For decades, the Cranbrook Wilderness Expedition has invited students to trade comfort for challenge, discovering resilience, leadership, and connection in the process. Few embody that spirit more deeply than Ian Perkins ’05, who first joined the Wilderness Expedition as a sophomore and has returned nearly every year since—now as a guide, mentor, and link between generations of Cranbrook students. Ian believes that his experiences first as a student and later as a Wilderness Expedition Leader shaped the confidence and leadership he draws on in every aspect of his life—including his ongoing service to Cranbrook today as president of the Cranbrook Kingswood Alumni Association.
“We absolutely love Ian,” says longtime coach and faculty member Chad O’Kulich. “He’s been an integral member of the Wilderness Expedition for over two decades. As both a student and guide, Ian has consistently demonstrated deep dedication, humility, and heartfelt commitment to giving back to the Cranbrook community.”
When Ian reflects on his first Wilderness trip in 2003, the memories are vivid and deeply personal. “My dad passed away two weeks before the trip,” he shares. “So for me, Wilderness became something entirely different. It came at exactly the right time. That solo experience and being completely alone in the woods for the first time gave me the space to process everything I was feeling. It was healing.”
Guides and fellow students surrounded him with compassion. “I had incredible instructors,” Ian recalls. “They knew what was happening and supported me in ways that I’ll never forget. The people - that’s what makes this program special.”
That first experience changed how Ian viewed community and leadership. “You’re thrown into this group of people, some you know and some you don’t, and you have to make it work. You learn to rely on each other. You learn that community isn’t optional, it’s what gets you through.”
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We were fortunate to sit down with Ian, who over the years, has continued to give his time, energy and talent back to Cranbrook, not only through the Wilderness Expedition, but also through the Cranbrook Kingswood Alumni Association. As current CKAA President, we had a few specific questions for him regarding the overall impact Wilderness has had on his life…
As a student on Wilderness, how did those early experiences shape your understanding of leadership and community?
It’s one of those things you don’t realize while it’s happening. As sophomores, you’re suddenly bound by a new set of norms - not your family’s, not your teachers’, but your crew’s. You figure out how to live, eat, hike, and solve problems together. Later, as a student leader, you begin to understand accountability and that leadership isn’t about being in charge; it’s about caring for others and being someone they can rely on.
It’s one of those things you don’t realize while it’s happening. As sophomores, you’re suddenly bound by a new set of norms - not your family’s, not your teachers’, but your crew’s. You figure out how to live, eat, hike, and solve problems together. Later, as a student leader, you begin to understand accountability and that leadership isn’t about being in charge; it’s about caring for others and being someone they can rely on.
Was there a moment that really tested you as a student leader?
Absolutely. My junior year, I came in a little overconfident. We had a tough uphill hike on day one, and I pushed too hard and ended up cold and exhausted, even showing early signs of hypothermia. It was a humbling moment. My instructors sat me down and said, “You’ve got to take care of yourself first so you can take care of others.” That lesson has stuck with me ever since - it’s the “put your oxygen mask on first” idea. You can’t lead effectively if you’re running on empty.
Absolutely. My junior year, I came in a little overconfident. We had a tough uphill hike on day one, and I pushed too hard and ended up cold and exhausted, even showing early signs of hypothermia. It was a humbling moment. My instructors sat me down and said, “You’ve got to take care of yourself first so you can take care of others.” That lesson has stuck with me ever since - it’s the “put your oxygen mask on first” idea. You can’t lead effectively if you’re running on empty.
Who were some of the people who influenced you most through Wilderness?
The people are what make this program truly special. Faculty who give up their spring breaks, spend nights in the rain, and do it all because they believe in this experience, it’s remarkable.
I think of people like Frank Norton, our program director back then, who really emphasized leadership and reflection. And of course, Chad O’Kulich. He’s been part of my life since before Wilderness, through soccer and beyond. The way he treats people, always looking for the positive, has had a lasting impact on me. Folks like Greg Miller, Jan Reelitz, and so many others have become lifelong friends and mentors.
The people are what make this program truly special. Faculty who give up their spring breaks, spend nights in the rain, and do it all because they believe in this experience, it’s remarkable.
I think of people like Frank Norton, our program director back then, who really emphasized leadership and reflection. And of course, Chad O’Kulich. He’s been part of my life since before Wilderness, through soccer and beyond. The way he treats people, always looking for the positive, has had a lasting impact on me. Folks like Greg Miller, Jan Reelitz, and so many others have become lifelong friends and mentors.
What lessons from Wilderness have stayed with you in your professional life?
A lot of my leadership philosophy comes straight from the program. Every night we’d debrief with three questions: What happened today? What did you learn? What will you do differently tomorrow? I use that same model at work. It’s all about reflection, communication, and striving for excellence. Wilderness teaches you to constantly look for ways to make things better, and that’s leadership in a nutshell.
A lot of my leadership philosophy comes straight from the program. Every night we’d debrief with three questions: What happened today? What did you learn? What will you do differently tomorrow? I use that same model at work. It’s all about reflection, communication, and striving for excellence. Wilderness teaches you to constantly look for ways to make things better, and that’s leadership in a nutshell.
Which part of the Wilderness culture resonates most with you?
“Stepping out of your comfort zone” is the big one. Growth doesn’t happen when things are easy. Every trip gives you that moment when you’re cold, tired, or unsure, and you realize you can do hard things. The other two are being present and awareness. In the woods, you’re not thinking about your phone or your next assignment. You’re right there, with your crew, completely engaged. That’s something I try to bring into every part of my life now.
“Stepping out of your comfort zone” is the big one. Growth doesn’t happen when things are easy. Every trip gives you that moment when you’re cold, tired, or unsure, and you realize you can do hard things. The other two are being present and awareness. In the woods, you’re not thinking about your phone or your next assignment. You’re right there, with your crew, completely engaged. That’s something I try to bring into every part of my life now.
What keeps you coming back year after year?
This program shaped everything about who I am - my values, my friendships, even my career. I’ve written Wilderness into every job I’ve ever had. Literally. I negotiate ten days of unpaid leave every March so I can guide. If I can help even one student find what I found out there, it’s worth every second.
This program shaped everything about who I am - my values, my friendships, even my career. I’ve written Wilderness into every job I’ve ever had. Literally. I negotiate ten days of unpaid leave every March so I can guide. If I can help even one student find what I found out there, it’s worth every second.
For Ian, Wilderness isn’t just an annual trip but a lifelong classroom.
“I’m not a traditional sit-in-a-classroom kind of learner,” he says. “Wilderness gave me a space where learning felt alive. Where leadership, teamwork, and self-awareness weren’t just talked about, they were lived.”
“Ian’s leadership style is grounded, thoughtful, and deeply impactful,” says O’Kulich. “He truly embodies the core values of Cranbrook, and his presence continues to shape the experience for everyone who steps onto that trail.”
After more than 20 years of returning to the backcountry, Ian still can’t imagine stopping.
“I don’t see a reason to,” he says with a laugh. “As long as my knees hold out, I’ll be there.”
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For information on activities of the Cranbrook Kingswood Alumni Association click here.
The dates of this year's Wilderness Expedition are March 4, 2026 - March 16, 2026. As of November 13, 2026, applications for Wilderness Leaders for the 2026 CK Wilderness Expedition are being accepted. Click here for more information.
To go to the main Alumni Welcome page click here.
“I don’t see a reason to,” he says with a laugh. “As long as my knees hold out, I’ll be there.”
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For information on activities of the Cranbrook Kingswood Alumni Association click here.
The dates of this year's Wilderness Expedition are March 4, 2026 - March 16, 2026. As of November 13, 2026, applications for Wilderness Leaders for the 2026 CK Wilderness Expedition are being accepted. Click here for more information.
To go to the main Alumni Welcome page click here.
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Ian Perkins '05 on Wilderness Expedition
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CKAA President Ian Perkins '05 at Reunion 2025
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Ian Perkins '05 as a sophomore on Wilderness Expedition
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Ian with his Wilderness Expedition group in March 2003
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