Dirtbag Rich

Michael Hughes is a 37-year-old river guide, training director, and year-round rafting company employee who’s built a stable yet unconventional life around whitewater. (@northwest.rafting.company)His journey started at age 19 on a canoe float down the Rio Grande, where he realized that working on rivers could actually be a job. Michael spent his twenties chasing the guiding season between California and Oregon, stitching together odd jobs to keep returning to the water. He built chicken coops, worked wine harvests, lead students on a gap year program in India and Nepal, and never let a “real job” get in the way of summer river trips.Now he manages a seasonal crew, runs guide training, and leads a handful of multi-day trips each summer. He lives in a camper during the rafting season in Southern Oregon and then returns north to Hood River, where he and his fiancée recently bought a house in White Salmon (technically, she's the landlord). His role includes intense bouts of hiring and logistics, but also off-season flexibility: long trail runs on weekdays, powder days in the winter, a rafting trip in Bhutan each fall, and plenty of personal river time for kayaking.We talk about Michael's path to financial independence without family help, the tradeoffs of guiding life (like missing most summer weddings), and how he finds meaning in late-night Milky Way sightings, watching kids growing up on trips over the years, and seeing his mom jump into the river for the first time at age 60.Michael also contributes to Whitewater Guidebook.Full transcript: dirtbagrich.com/michael

Jack Schott is a 36-year-old summer camp consultant, former camp founder, and self-directed learning advocate who spends a lot of time thinking about money. (jackschott.com)Jack occasionally earns $1,500-$3,500 in a single day by running corporate trainings and camp staff workshops: work that doesn’t always light him up, but work that is very useful for buying time, freedom, and very possibly, another summer camp that he can direct.Jack describes the tension he feels between wanting to do meaningful work and not wanting to be tied down. At his most purposeful, he was co-running a camp in upstate New York with his ex, building cabins by hand and forming deep relationships with kids and staff—but he felt trapped. Now he’s trying to design a setup where he can direct a camp each summer without needing to live on site year-round.He also shares how he thinks about money strategically: not just for personal comfort, but as a tool for long-term impact, particularly in making camps more self-directed and less top-down. In this vein, he describes how an average 22-year-old could quickly build a high-flexibility career from scratch by cold-emailing lawn care companies (or a similarly "boring," everyday field of work).Jack is less focused on outdoor adventure than past guests, but he’s laser-focused on building a life of flexible work and purposeful contribution. His version of "dirtbag" is getting to play outside with kids, every single summer, for the rest of his life.Full transcript: dirtbagrich.com/jack

Morgan Sjogren is a 38-year-old environmental writer who has spent the last seven years living as a modern-day desert nomad, crafting a freelance journalism career while residing primarily in the remote wilderness of Utah's Canyon Country. (morgansjogren.com)After growing up in Southern California suburbia and spending her twenties pursuing a marketing career, Morgan left her more conventional life at age 30 to live full-time in the back of a Jeep, sustaining herself on dumpster-dived ingredients and gas station burritos. For the past seven years, she has made the Colorado Plateau her home, spending much of her time in solitude among the sandstone canyons and mesas, with just a fraction of her year in actual cities. She explains how nature became her true home rather than a playground, and how this relationship with the desert has shaped both her writing and her sense of purpose.We discuss her path from suburban trail runner to high desert hermit and how she cobbles together income through freelance writing, photography, public speaking, house cleaning, and modelling. Morgan describes her two books—the dirtbag cookbook Outlandish and the historical narrative Path of Light—and how retracing 1920s expeditions through Glen Canyon helped her find both community and her current partner Aaron. She explains why she feels called to advocate for public lands through her writing, and how the desert has repeatedly shown her that even in apparent solitude, she is never truly alone. For Morgan, being "dirtbag rich" means having clean water, clean air, healthy ecosystems, and places that are open and welcoming to all people.Full transcript: dirtbagrich.com/morgan

In this engaging conversation, Blake Boles, a writer and traveler known for leading self-directed adventures for teens, shares his journey and philosophy on freedom, purpose, and security. He discusses his love for minimalism and owning less, while emphasizing the importance of human connections formed through dance and travel. Blake critiques conventional lifestyle literature and reflects on his own influences from alternative communities. The duo also explores the transformative power of unschooling and wilderness experiences, highlighting the challenges and joys of a non-traditional path.

The host reflects on the balance between time, money, and purpose, all through the lens of outdoor adventures. Excitement bubbles over as they share updates on both the podcast and an upcoming book. Listeners are encouraged to suggest diverse guests to inspire richer conversations. It's all about embracing a lifestyle that values exploration and meaningful experiences!

Kaya Lindsay is a 32-year-old climber, filmmaker, vanlife veteran, and accidental gym owner in Moab, Utah. (onechicktravels.com / @onechicktravels)In her early twenties, Kaya fell in love with bouldering at a Santa Cruz gym, met a tattooed vegan woman with a Sprinter van, and realized she could climb full-time. She built out a van, hit the road, and spent four years chasing perfect weather and fleeting friendships from Bishop to Squamish to Indian Creek. Along the way, she hustled together a dirtbag media career: filming, blogging, scoring gear deals, and slowly building a name with her One Chick Travels YouTube series, which spotlighted the unseen women shaping the climbing world.Kaya talks about living on $1,000 a month, the hidden privilege of trust fund dirtbags, and the unspoken rules of social capital in the outdoor scene. She describes what finally pushed her off the road: constant vigilance, repeating the same small talk, and never knowing if her community would stick around when the rain came. Kaya also describes why settling down in Moab felt like upgrading to a bigger container, not a smaller one.We get into how a base jumper literally fell out of the sky and became her business partner, what it’s like running Moab’s first climbing gym, and how building a rooted, weather-independent community has changed her life. Kaya also opens up about the neurodivergent undertones of dirtbag culture, the bittersweet question of what happens to aging climbers, and how it feels to finally walk into the grocery store and see someone who knows your name.Full transcript: dirtbagrich.com/kaya

Peter Kowalke is a 45-year-old relationship coach, "half monk," and Bangkok-based nomad who has crafted a life of radical simplicity. (peterkowalke.com)Peter explains his life through multiple levels of understanding—from the simple "I help people have good marriages and travel around the world doing it" to the complex spiritual journey that led him to nearly become an ordained monk in the Vedanta tradition. He shares how he lives on as little as $9,000 a year while occasionally earning up to $200,000 through his three income streams: relationship coaching, content marketing, and freelance writing.We explore his nomadic lifestyle across Southeast Asia and Africa, his philosophy of distinguishing wants from needs, and his creative frugality, such as his airport food court "monk's bowl" approach to eating. Peter reflects on the challenges of his borderless existence during the pandemic, when global "tribalism" left him without a community safety net despite his carefully designed life of freedom.Peter discusses the apparent contradiction between his relationship coaching and monastic leanings, his unschooling background that taught him to question conventional wisdom, and how he builds community through his popular Bangkok dinner parties. Peter's story illuminates the rewards and challenges of crafting a life that prioritizes spiritual growth and human connection over material possessions and geographic roots.Full transcript: dirtbagrich.com/peter

Luke Mehall is a 46-year-old climber, writer, and self-described dirtbag who turned a one-time zine into a print publishing business and podcast. (climbingzine.com / @lukemehall_writer)After escaping a Midwest upbringing and mental health struggles in his early twenties, Luke found stability through poetry, climbing, and the encouragement of writing professors at a small liberal arts college. He spent a few years dirtbagging full-time—living under rocks, washing dishes, and following the ethos of Jack Kerouac and the Grateful Dead—before settling into a more balanced life.Today, Luke lives between Durango (Colorado) and Potrero Chico (Mexico). He runs The Climbing Zine, hosts the Dirtbag State of Mind podcast, and writes books. He supports himself through selling print subscriptions, ads, and merchandise.For Luke, climbing is still central, but now it fits into a sustainable routine that includes weightlifting, rest, and solid friendships. We talk about the modern flavors of dirtbagging, the myth of the four-hour work week, what purpose looks like without kids, and how exercise—not medication—became his lifeline. We also get into the logistics of running a niche print publication in a digital world, and why handing someone a printed zine still matters more than a Substack link.Luke also reflects on what it means to grow older in a lifestyle built for youth. He’s seen what happens when people cling to the dirtbag dream too long—loneliness, stagnation, the slow unraveling of purpose. For him, the goal was always evolution: building a life that still honors climbing and creative freedom, but with enough structure to stay grounded. He doesn’t envy tech workers or trust the illusion of job security, but he does believe in balance, community, and the kind of autonomy that lets you shape your own rhythm—and enjoy frequent midday climbing sessions.Full transcript: dirtbagrich.com/luke

Courtney Bierschbach is a 36-year-old nonprofit consultant and writer who calls a converted fire rig named Rigby her winter home. (thewanderingcourt.substack.com)Courtney tells the story of her unconventional path—from graphic design and incentive travel jobs that left her drained, to a joyful stint teaching Leave No Trace in national parks, to eventually launching her own consulting business that supports mission-driven nonprofits. She and her husband Nick, both self-employed with control over their time, spend Michigan winters chasing sunshine out west in their 4×4 ambulance, loaded with mountain bikes, paddleboards, and their dog.She describes how a cancer diagnosis tested her self-employment setup—and how her clients stepped up with care, flexibility, and even soup. We get into how she built a stable consulting income (~$60K/year on ~25 hours/week), her passion for outdoor education, and why she’ll never work under fluorescent lights again.Courtney also reflects on marrying young, skipping kids, and throwing a pancake-flipping, s’mores-filled wedding that included a Guinness World Record holder. Her version of a rich life? Flexible work, meaningful projects, solo bookstore trips in Scotland, and the freedom to hit the road whenever the snow starts piling up.Full transcript: dirtbagrich.com/courtney

Miya Tsudome is a talented outdoor photographer and climber based in Bishop, California, who transformed her life after a summer job in Yosemite. She candidly shares her journey from dealing with student debt to embracing a lifestyle prioritizing climbing and adventure. Miya discusses the balancing act between financial insecurity and creative freedom, and how her father's influence shaped her outlook. She also touches on the insecurities of freelancing and her passion for capturing nature’s beauty, blending her artistic pursuits with her love for climbing.