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.

Diana Proemm is a 54-year-old ski bum, adaptive sports professional, dual US-German citizen, and lifelong wanderer who has spent three decades saying yes to unlikely opportunities. (dianaproemm.com)

Diana describes leaving Ohio in the mid-1990s, bouncing between ski towns, remote lodges, and outdoor jobs, and building a life through curiosity, persistence, and conversations with strangers. From working in Alaska’s grizzly bear country to hitchhiking through Chile, volunteering on organic farms in New Zealand, and repeatedly selling nearly everything she owns, Diana’s story never really settles down.

Along the way, she became a certified recreation therapist and adaptive sports director, helping people with disabilities access the outdoors while slowly piecing together enough financial stability to keep chasing freedom. We discuss seasonal work, Workaway gigs, online income, living cheaply abroad, why she believes many women underestimate what they're capable of, and the social dynamics of working with wealthy clients at the Yellowstone Club.

Now living in the Austrian Alps, Diana reflects on getting laid off, starting over in a new country, and maintaining faith that the next opportunity will appear when she needs it. At an age when many people are planning retirement, Diana doesn't know where she'll be next year—but that's never stopped her before.

Madeline Hryse is a 28-year-old traveler, climber, and cyclist who spent four years moving overland across Latin America and Asia—sometimes alone, sometimes with friends and strangers she met along the way—before cycling 14,000 kilometers from China to Sweden. (@very__odd)

Madeline grew up in a family that treated adventure as a normal part of life, but her father was the biggest influence. A mountaineer, bicycle tinkerer, and dirtbag before dirtbagging had a name, he spent his youth hitchhiking to the Rockies and disappearing into the mountains for weeks at a time. Although he died when Madeline was sixteen, she reflects on how much of her own wandering life feels connected to his example.

After studying fashion merchandising and selling women’s shoes at Nordstrom, Madeline escaped on what was supposed to be a six-month trip through Central America during the pandemic. Instead, she spent the next four years traveling. She taught English in South Korea, saved $10,000 through extreme frugality, trekked through Nepal, climbed her way across India and Sri Lanka, and continued through Pakistan and Southeast Asia while stretching her savings far beyond what most people would think possible.

Along the way, Madeline became increasingly drawn to overland travel and the freedom of moving through places slowly. Rather than chasing famous sights, she sought out climbing communities, stayed with locals, camped whenever possible, and built friendships that carried her across continents. She explains why having a purpose while traveling made her happier than following the standard backpacker trail and how she often spent less than $500 per month while on the road.

Eventually, a fascination with maps, Central Asia, and the Silk Road inspired her biggest adventure yet: a year-long bicycle journey from China through Kazakhstan, Kyrgyzstan, Tajikistan, Uzbekistan, the Caucasus, Turkey, and Europe. We discuss the realities of long-distance bike travel, the experienced Austrian cyclist who helped shape her approach to the road, and why she gradually became more interested in lingering somewhere beautiful than covering huge distances each day.

We also talk about returning home after years abroad, resisting the pressure to pursue graduate school and a conventional career, the modest family support that helped make her travels possible, and her growing desire to spend more time with family and build deeper relationships. Madeline is currently preparing to ride the Continental Divide before relocating to Spain, where she’ll attempt to balance adventure with something that has become increasingly important to her: putting down roots.

Full transcript: dirtbagrich.com/madeline

In this wide-ranging conversation, Ryan Jordan of BackpackingLight.com interviews Blake about Dirtbag Rich. Topics include:

• The historical meaning of “dirtbag” in climbing, thru-hiking, and outdoor culture
• How dirtbag culture has traditionally balanced freedom, poverty, adventure, and insecurity
• The risks and trade-offs of choosing flexibility over conventional career advancement
• Housing strategies that support a dirtbag-rich lifestyle, including roommates, small homes, van life, travel, and shared living
• How cultural expectations around home ownership, status, and consumption shape lifestyle decisions
• Why relationships, community, and the ability to show up for others may be overlooked forms of wealth
• The role of privilege in pursuing a dirtbag rich lifestyle
• How to pursue outdoor freedom without romanticizing irresponsibility, poverty, or precarity

Find the original episode (including a fairly critical discussion thread) here: https://backpackinglight.com/episode-146-dirtbag-rich-with-blake-boles/

This conversation was originally published on May 1st, 2026.

Eric Darby is a “deeply blue-collar” builder, off-grid tinkerer, helicopter pilot, and grandfather who has spent most of his life avoiding normal jobs.

Eric never made much money—his lifetime average income is about $7,500 per year—but he still managed to buy 16 acres in western Colorado and fill it with Earthships, tiny houses, workshops, kinetic sculptures, and other hand-built structures. He describes his pride in being able to weld, wire, plumb, and frame his own buildings, and why waking up with a construction problem to solve feels more meaningful than any paycheck ever could.

Although Eric lives an extraordinarily sustainable life—collecting rainwater, generating his own solar power, charging his electric car at home, and building with salvaged materials—he arrived there through thrift and curiosity, not environmental ideology. As he puts it, his connection to nature is often less about hugging trees and more about “cutting down a tree in my way” or trapping the squirrel that burrowed into one of his tire walls.

We discuss his stint as a teenage garbage collector, the dirtbag motorcycle years, flying helicopters in Vietnam and Alaska, and the freedom that comes from needing very little money. Eric says his strongest sense of purpose comes from building things for his children and grandchildren, not from trying to set an example for the world—though many young visitors leave his property inspired by what they see.

At the heart of Eric’s story is a simple conviction: he would rather be homeless than spend his life in a conventional job fixated on making money. For anyone who suspects there must be another way to live, Eric offers a powerful and deeply practical example.

Full transcript: dirtbagrich.com/eric

Claire Pomykala is a 26-year-old bike tourer and accidental influencer who walked away from a $115,000 tech job because it made her feel physically and mentally unwell—and replaced it with a loose mix of guiding, bikepacking trips, and independent projects. (livingbybike.com / @livingbybike)

Claire traces her path into cycling back to a campus bike co-op that offered an unexpected sense of belonging. Soon after graduating college, she skipped the traditional next steps and biked from Atlanta to Baltimore, then spent nearly six months riding solo across Europe. What began as an escape from jobs and expectations turned into a long-term way of life, including later trips across the U.S. and New Zealand.

She explains what makes bicycle touring distinct from other forms of travel, why it creates a more immersive and uncomfortable experience, and how her social media following grew at the exact moment she stopped traveling. We talk about her brief time in tech, where she jumped from $15/hour jobs to a six-figure salary despite having little background in the field: a position she describes as largely meaningless and difficult to tolerate, but financially useful, as it allowed her to save money, quit, and return to a more flexible lifestyle.

Now, Claire earns money through a combination of leading occasional luxury bike tours for a company, organizing her own smaller (and shockingly affordable) bikepacking trips, and occasional brand partnerships. At the same time, she’s trying to maintain distance from social media, even as it remains her primary source of clients.

We also discuss her essay “I’d rather be kind of poor than work most jobs,” the tradeoffs between stability and autonomy, and her preference for time-rich, flexible living over a consistent paycheck, even as she acknowledges the uncertainty that comes with it.

Full transcript: dirtbagrich.com/claire

Scott Stillman is a 53-year-old writer, backpacker, and desert wanderer who built his life around walking canyon country instead of working full-time. He’s the author of I Don't Want to Grow Up and seven other books. (scottstillmanblog.com)

Scott traces his evolution from skateboarding teenager to normie bank employee in Ohio to full-time freedom seeker in Colorado. Along the way, he explains why he’s always prioritized time over money, how he and his wife built a life around working as little as possible, and why most people are asking the wrong question when it comes to careers.

We get into the specific ways he pulled this off, from compressing an insurance sales job into two days a week to negotiating a car sales role down to weekends only. Now living in Durango, Scott earns a living from his books—spending about two hours a day on social media—and spends the rest of his time hiking, backpacking, and disappearing into canyon country. He also explains how writing accidentally became his path to freedom, the role a good editor plays, and why he ditched photography to start documenting his experiences with words.

We also get into the philosophy behind his work: why “this reeks of privilege” is the most common critique he hears from young people on TikTok, why he thinks that’s missing the point, how starting with a beat-up car and a few hundred dollars can still lead to a life outdoors, and why you don’t need to have your whole life figured out—you just need to go.

Full transcript: dirtbagrich.com/scott

In this special episode, Blake talks with his old friend, summer camp co-leader, and High Sierra backpacking partner, Fred.

Born and raised in Valencia, Spain, Fred brings a European perspective to the question of whether it's possible to become dirtbag rich in a place with different cultural norms and a lower income than the United States.

Fred also discusses how professional trail runners transition away from 20-something dirtbag lives and the (positive) challenge of being spoiled by purposeful work—including deeply meaningful professional relationships—early in life.

Finally, Fred asks Blake about his new book, released today: Dirtbag Rich: High Freedom, Low Income, Deep Purpose. What did it take to write it? How much did it cost to publish? What comes next? And where can people find it?

Dave Whitson is a 40-something high school history teacher and Camino de Santiago guidebook author who has crossed the United States on foot, spent six of the past twelve months traversing Italy, and taken countless student groups on long-distance walking adventures. He has no phone plan, gym membership, or anything resembling a vice. He writes powerful travel narratives, adores the challenge of working with sharp teenagers, struggles with relationships, thinks frequently about death, considers himself a sort of “parasite” on conventional society, and knows more about the Camino (and other modern pilgrimage routes) than pretty much anyone on earth. (davewhitson.com)

Full transcript: dirtbagrich.com/dave

Ryan Van Duzer is a 46-year-old adventurer, filmmaker, and bike-powered storyteller who has spent the past two decades turning his obsession with movement into a full-time career. (duzertv.com)

After a two-year Peace Corps stint in Honduras, Ryan skipped the flight home, bought a $700 bicycle, and pedaled 4,000 miles back to Boulder, Colorado—a trip that changed his life and set him on a path toward sharing human-powered adventures with the world. What followed were years of scraping by as a travel-channel hopeful, living with his mom, chasing production gigs, and refusing to quit when every practical voice said he should.

At age 36, he walked away from TV and started over on YouTube. Now he earns a six-figure income through ad revenue, Patreon, bike-design royalties, and public speaking—but he still rides everywhere, owns no car, and keeps his expenses low.

We dig into the years when he lived on almost nothing, the slow grind toward creative control, and the constant tension between documenting life and living it. Ryan opens up about how his “get off the couch” mantra evolved from personal fitness to something broader: a way of rebuilding social fabric in an age of isolation.

We also discuss the doubts that creep in as he ages out of being the “young, spunky YouTube adventurer,” the exhaustion of constant content creation, and why the freedom he fought for still feels worth it.

Full transcript: dirtbagrich.com/duzer