Blake Boles: live at Maria's Bookshop in Durango, Colorado

In this live talk, delivered at Maria’s Bookshop in Durango, Colorado on May 19th, 2026, Blake introduces the mountain-town question that has long obsessed him: How do you build a life with enough time, money, and purpose to fully enjoy the outdoors while your body still works?Blake shares his own path from suburban California kid to outdoor educator, unschooling travel entrepreneur, and writer—and explains how he gradually built a lifestyle where he works relatively little, spends lots of time in nature and community, and measures wealth less by money than by freedom, meaningful work, relationships, and unforgettable experiences. He also explains why both classic dirtbagging and the standard American dream eventually lead to burnout, and why the people most drawn to this path tend to be “moderately privileged and highly idealistic.”Throughout the talk, Blake shares stories from his many Dirtbag Rich interview subjects, all of whom have found radically different ways to balance work, adventure, security, and freedom. He also discusses modern economic pressures, “greedy jobs,” social comparison, and why outdoor dreams are often difficult to postpone until retirement.At the end, Blake takes three audience questions: one about balancing personal freedom with service to others, another about the guilt and social tradeoffs of living cheaply and unconventionally, and a final question about overcoming the fear of leaving a stable full-time job to pursue a more dirtbag rich life.