What It Means to Finish Something Hard With the Person Who Knew You Before Any of This

My best friend Michael Whalen has known me since college, long before Dalton Johnson Media existed, long before any brand client, long before a decade of photography and filmmaking across seven continents shaped who I am professionally. Finishing our five-day paddleboard circumnavigation of Lake Tahoe with him specifically, rather than solo or with a professional crew, meant something that's taken me a while to fully articulate. Here's what I've landed on.

Why the Person Matters as Much as the Accomplishment

Seventy-two miles is seventy-two miles regardless of who you paddle it with. The physical accomplishment doesn't change based on your company. But the meaning of that accomplishment changes completely depending on who's standing next to you when it's done, and finishing with Michael carried a specific weight that finishing alone or with someone I'd just met professionally never could have.

What Michael Knew That No One Else on This Trip Could Have

Michael knew me before any of the identity I've built professionally existed. He knew me as a college kid who loved surfing, before the van, before the seven continents, before any of the credentials that now define how most people who meet me understand who I am. Finishing something this physically and logistically demanding with him meant finishing it with someone who could see past all of that context to something more fundamental and longer-standing.

How This Differs From Finishing With a Professional Crew

A professional crew, however skilled and however good the working relationship, relates to me primarily through the lens of the current project and my current professional identity. Michael relates to me through fifteen-plus years of actual friendship, most of it having nothing to do with photography, filmmaking, or brand partnerships at all. That difference shaped every part of the trip, from how we made decisions together to what we actually talked about during the quieter stretches.

What Almost Finishing Without Him Taught Me

For about twenty-four hours in the middle of the trip, when it looked like Michael might need to leave early, I got a preview of what finishing this without him would have actually felt like. Logistically, I could have managed it. Emotionally, it would have been a completely different project, closer to the solo expeditions I've done throughout my career than to what 72 Miles of Blue actually became. That near miss clarified, more than anything else on the trip, exactly how much his specific presence was contributing to what this project meant to me.

Why This Kind of Friendship Is Increasingly Rare in Adult Life

Most adult friendships, mine included, run on a schedule of infrequent check-ins, work and family responsibilities crowding out the kind of extended, uninterrupted time together that this trip required. Finding someone willing to commit five days to something this physically demanding, someone who's known you long enough to still relate to you outside your professional identity, is genuinely rare once you're a decade or more into building a career and a life. That rarity is part of what made finishing with Michael specifically feel significant.

What This Trip Changed About How I Think About Old Friendships

Since finishing 72 Miles of Blue, I've thought more deliberately about which relationships in my life have this same quality, people who knew me before any current version of my identity, and how rarely I actually make space for real, extended time with them. This trip was, among other things, a reminder that those relationships need active investment, not just goodwill, to stay meaningful across years and distance and the demands of building a career.

What This Realization Changed About How I Plan Future Projects

Since finishing this trip, I've become more intentional about who I invite into demanding projects, weighing not just professional competence but also the depth and history of the relationship itself. Some future expeditions will genuinely call for a professional crew, and I'm not suggesting every project should be built around old friendships instead. But I'm no longer treating that choice as automatically obvious, and I think more carefully now about what kind of relationship I actually want at the center of a given project before defaulting to whichever arrangement is most logistically convenient.

What I'd Tell Someone Weighing This Same Decision

If you're planning something demanding and have the option to bring either a more qualified stranger or a less experienced old friend, sit with what you actually want the project to produce beyond the physical accomplishment itself. If the relationship and what it might deepen matters as much to you as the outcome, that's worth weighing seriously against pure logistical efficiency. Michael and I finished 72 Miles of Blue with something neither of us could have gotten from a more efficiently executed version of the same trip with someone else.

What Michael Has Said About What the Trip Meant to Him

Michael and I have talked since about what this trip meant to each of us individually, and while our specific reflections differ in the details, the through line is the same for both of us, gratitude for having made the time, for having actually done this rather than continuing to talk about doing something like it someday. That gratitude, more than the mileage or the physical accomplishment, is what I expect will stay with both of us longest, long after the specific memory of any single mile or crossing has started to fade.

What I'd Say to Someone Hesitant to Ask an Old Friend for This Kind of Commitment

Asking someone to give up five days for something physically demanding can feel like a big ask, especially with a friend whose life is as busy and complicated as your own. I hesitated before asking Michael, worried it was too much to request. What I've learned since is that most people, when asked sincerely, are more willing than you expect to make room for something meaningful, and the worst outcome of asking is simply hearing no, which costs far less than never asking at all and living with the regret of that silence instead.

Before You Close This Tab

Why did finishing a seventy-two-mile paddle with a college friend matter more to you, hypothetically, than finishing it solo would have?

Who in your own life knew you before your current professional identity existed, and when did you last spend real, extended time with them?

What would it take for you to commit several full days to something demanding with an old friend, given the current shape of your life?

How does finishing something hard change depending on who you're finishing it with, in your own experience?

Dalton Johnson is a photographer, filmmaker, and brand storyteller based in South Lake Tahoe, California. Over the past decade he has worked with brands including Patagonia, GoPro, Arc'teryx, Four Seasons, Nike, Rivian, and Ford Bronco across all seven continents. He is the creator of the Follow The Journey distribution framework, which has produced over one million organic views per 30-day cycle without paid media. His work includes two published books, an award-winning documentary that aired on PBS, and more than fifty commercial spots directed. He runs Stories by Dalton on Substack, read by more than 34,000 subscribers.