Blog 4: Why I’m Building Something Small on Purpose

If you read “The Higher I Climbed, the Less I Knew Myself,” you know what three decades of leadership cost me. Title by title, I traded the people who knew me for the people who only knew my position. By the end, I was the new dean, the latest associate provost, known by my CV before anyone had a chance to know me.

The Camino gave that back to me, and it did it through something almost absurdly simple: nobody knew my title.

For the first time in decades, I was just Rob. Not Rob the department chair, or Rob the dean, or Rob the provost. Just Rob, carrying everything I owned on my back. The other pilgrims didn’t know where I’d worked or what I’d accomplished or where I lived. They didn’t care. They got to know me for who I was right there on the road, and for why I was walking. There was nothing to manage and nothing to prove. It was the most literal kind of starting over I’ve ever experienced, and it turned out to be exactly what I needed.

I spent a lot of those walking hours thinking about the parts of my life that had brought me real joy, the roles I’d had before I started climbing. One of those was my time as a librarian. Another was travel, which I’ve loved for as long as I can remember. Somewhere around day five or seven, I put those two things together and landed on an idea: thematic, literature-based trips, similar to international programs I’d led at the universities where I’d worked.

It’s still a good idea. I’d enjoy doing it. There’s real value in bringing people together around books and places and ideas, and there’s nothing wrong with building something that’s both intellectually engaging and just plain fun for the people who join.

But it wasn’t the idea that resonated.

What I was actually looking for, without fully realizing it, was a way to be useful to someone going through something hard. Coaching is like teaching, like advising, like mentoring, all things I’d done for 36 years in education, just without the title attached to them. And I’d been struggling, for longer than I want to admit, to find my own way forward. I talked to people. I read the books, Bridges, Brooks, the ones that name what you’re going through better than you can name it yourself. None of it gave me the clarity I needed. It wasn’t until I had the quiet of the walk itself, the reflection, the meditation, the prayer, that I started to see who I actually was and what I was actually meant to do.

That’s the thing I wanted to give other people. Not just the walk itself, although the walk matters enormously. What I wanted to give them was the structure I’d built around it, coaching before they ever set foot on the Camino, presence and conversation during the days on the trail, and follow-up in the weeks after to help them process what surfaced and decide what to do about it. The literature trips would let me share something I love with people who’d enjoy it. Coaching lets me walk with someone through a moment that’s actually difficult, and help them come out the other side knowing more about themselves than when they started.

That felt like the more meaningful work. It still does.

I want to be honest about something. Ultreia was never meant to be my next career. I’m close enough to retirement that what I needed wasn’t another job to build. Rather; it was something I genuinely loved, something useful to the people who joined me, and something that could fit into the life I already have. One or two trips a year lets me do that now, before I’ve even left my day job. It’s not a stepping stone to something bigger. It’s the thing itself.

Going big, in business as in a career, means spreading yourself thinner. Bringing in other coaches, scaling the offering, growing Ultreia into something bigger than me would mean trading the very thing that makes it worth doing. I’d be managing a business instead of walking with people. I’d be climbing another rung of a different ladder, and I already know where that road leads.

Staying small means I can actually know the people I work with. Not their resumes. Not their professional narratives. Them, what they traded away, what they’re afraid to want, what makes them feel alive again when they stop performing long enough to notice.

That is not something you can do at scale.

Ultreia exists because I built a curriculum for my own Camino, a daily practice of reflection and questioning that turned a long walk into something more than a walk. I spent real time on it. I don’t think the people I guide should have to reinvent that process from scratch. They should be able to show up, put one foot in front of the other, and spend their energy on themselves and the path ahead, not on figuring out the framework.

That’s what I’m offering. Not a platform. Not a program with a waitlist and a funnel. A guide who has made this walk, who built the tools because he needed them, and who would rather enjoy this work than let it take over his life.

Small is not a limitation. It’s the whole point.

Rob is the founder of Ultreia, a coaching and pilgrimage practice for professionals at the threshold. Learn more at www.walkwithultreia.com.