John Winsor has lived many lives: setting an FKT on Kilimanjaro before the term existed, surviving an avalanche in the Selkirks, building and selling companies, serving on Black Diamond's board, and now researching organizational innovation at Harvard. In this conversation with Steve House, he traces the thread connecting these experiences—what he calls "the explorer's mindset." Whether pioneering bike-sharing programs as an ad agency or asking "why not?" instead of "why?" in academic research, Winsor has spent his career venturing beyond the horizon and bringing discoveries back to his community.
The conversation moves into profound territory when Steve asks about Winsor's wife Bridget, who struggled with late-onset bipolar disorder and took her own life after 32 years of marriage. Drawing on Stephen Colbert's perspective about experiencing the full spectrum of human emotion, Winsor reframes tragedy not as something to be walled off but as an honor to witness and integrate. This openness extends to his recent prostate cancer diagnosis—another experience he approaches with curiosity rather than fear, asking "what does this feel like?" rather than retreating from difficulty.
The episode culminates in Winsor's surprising answer to how he wants to be remembered: he doesn't. Inspired by Hindu traditions, he longs to become "a ghost in the machine"—present, curious, connected, but freed from the burden of maintaining identity or legacy. It's a vision of equanimity that, as Steve notes, doesn't contradict the desire to bend the arc of history, but somehow completes it.
Special Offer to Listeners: Receive free four week samples of our most popular training plans, visit uphillathlete.com/letsgo
Write to us at coach@uphillathlete.com
