The Question That Stopped Me Cold – How one moment at Skamania Lodge made me rethink my “why”

It happened at the cocktail reception before dinner. The sun was starting to drop behind the trees at Skamania Lodge, the white tablecloths on the garden patio lifting in the breeze, and the smell of dinner drifting across the lawn. One of the participants, beer in hand, approached. 

“So, I have a question for you. This morning, you asked about our “why”  — why we came to this program. What is your why? Why do you travel halfway across the country three or four times a year to guide this program?”

In five years, a dozen cohorts, and over two hundred participants, no one had ever asked me that.

I gave the first answer that came to mind: “I love the story, I love storytelling, I love seeing the lightbulb moments in people’s eyes when something connects.”

True enough. But the question stayed with me—over dinner, around the campfire that night, on the flight home. Why do I really do this? Especially now, when leaving Carmen is harder and harder with each trip.

Why – Deep Learning

I am honored to have been selected by my client, FCCS, to help build this program. What began as Carmen’s and my journey to follow the Lewis and Clark Trail blossomed into an entirely new career when Jean Canty Segal of FCCS read some of my writing about leadership and Lewis and Clark. She invited me to meet with a team of people in Seattle to discuss building the program. I was thrilled to be selected as a part of the team. 

It stretched me. I learned so much in those 18 months of developing the program. Not so much about Lewis and Clark, but about leadership development programs, experiential learning, and the discipline to bring their vision to life. I walked away from every meeting we had with new insights and new perspectives. 

From Sean Murray, I learned how to pace an experience so it flows.

From Matt Walker, I learned how the outdoors can carve a lesson deep into memory.

From Jared Nichols, I learned to stand in the future and imagine beyond the present.

My why? The learning never stops — and I love what we built.

Why – Continuous Learning

We launched the program in 2021, and since then, I’ve had the privilege of leading a dozen cohorts through the key concepts of Vision, Team Building, Overcoming Obstacles, Developing Resilience, and Proceeding On.

It never gets old. It never becomes routine. It never gets mailed in.

Each group arrives ready — hungry to learn, hungry to grow as leaders. They bond quickly and deeply. They are open to new and sometimes uncomfortable experiences. They push themselves. They challenge each other.

It’s a joy to watch it happen. Twenty strangers on the first night become friends, teammates, colleagues by the end of day one. They come from different industries, different parts of the country, different perspectives — yet they share a willingness to listen, to learn, and to support each other.

And I learn from every single one of them. Sometimes it’s an insight shared quietly after the hike or the aerial course. Sometimes it’s a reflection offered around the campfire, or a look across the table that says, Yeah, that makes sense now. Other times it’s a suggestion scribbled on a survey form (yes, we read every one), or a perspective I’d never considered, or a question no one had ever asked me before.

That constant exchange — giving and receiving, teaching and learning — is one of the things that keeps me coming back.

Why – Legacy

One of the leadership lessons we teach in the closing module is about legacy, not necessarily the legacy you leave behind when you leave this earth, but the legacy you leave behind in your team, in your teammates, when you transition to a new role or a new job. What do you hope they carry with them? 

I have grown so much through the program, sometimes taking to heart the very lessons I am teaching, perhaps in a different way. Like celebrating victories. As the facilitator, I too, need to celebrate victories, like the successful conclusion of another cohort. 

I have been thinking a lot about legacy as I approach the end of my career, as I move into the final chapter of life. What do I want to leave in the hearts and minds of others?

Family, of course. My wife Carmen — my partner in all things. Good times — tough times, through it all, I want her to carry my love in her heart. My sons, Jeremy and Brad. I see pieces of me in them — different pieces, similar pieces. Yet, they are their own men, teaching me each and every day. My grandkids  — Braxton, Jordan, Jasper, and Hayden, step grandkids Ari, Avery, and Henry, and step grandkids from a son’s prior marriage, Donny and Charity. Legacy.

The Indiana CIO Network. A group of IT professionals across Central Indiana and beyond. What started as five colleagues having lunch has grown into a group with over 400 members. Each member brings their insights and expertise  —  and their willingness to share and support each other. A new group of leaders have taken the reins and the group is thriving! Legacy. 

The Lewis and Clark Experience: A New Way Forward. There will come a time when I no longer serve as a guide for the program. Having the program on a solid foundation is one of the reasons I have poured my heart and soul into it. It is why we fine-tune it almost every time. That’s why I rehearse until I can forget the script and speak straight from the heart. Legacy.

The Journey

When Carmen and I first set out to follow the Lewis and Clark Trail, we had no idea what we’d discover. It became the theme of our life, the shape of my career, and the heart of my next book — Uncharted Moments Along the Lewis and Clark Trail – A Love Story.

I suppose that’s my real why: to keep the story alive — for the people in the room, for the people I love, and for the people I’ll never meet.

— Jeff

P.S. Over the next few months, I will be sharing more from my upcoming book, Uncharted Moments Along the Lewis and Clark Trail – A Love Story. If you want to be in the know as it proceeds through the publishing process, sign up for my newsletter in the side panel of this page!