Diana Grijalva is a 42-year-old outdoor educator, international guide, and almost-astrophysicist who hasn’t paid rent since 2008. (@diana.grigri)

Diana explains how she lives on seasonal wages, why she’d rather sleep in a van or hostel bunk than clock 40 hours a week, and how flexibility lets her drop everything to show up for family when it matters.

We get into her peak dirtbag years—dumpster diving, living on $7,000 a year, breaking ice off her tent in Joshua Tree—and how she’s sustained the lifestyle into her forties. Diana shares her favorite climbing hubs from Mexico to Turkey, the grind and charm of hostel life, and why she sees most jobs as “stealing people’s lives.”

She also talks about the unglamorous math behind dirtbagging: stretching cheap food and used gear, picking work that covers the basics, and saying no to anything that eats into her freedom. She lights up describing her rotation of winter haunts—Joshua Tree, Red Rocks, Moab, Potrero Chico, Greece, Spain, Sri Lanka, India, Morocco—each one a way of outsmarting the cold while deepening her love for new cultures.

Full transcript: dirtbagrich.com/diana

Julieta Duvall is a 42-year-old flight attendant, unschooling mom, and part-time poet who spent years chasing job security before realizing that freedom mattered more. (@the_unschooling_lifestyle)

Originally from Mexico, Julieta studied law, dropped out, and ended up taking the midnight shift as Spirit Airlines’ only Spanish-speaking reservations agent in Michigan. One year later, she joined the first class of flight attendants hired after 9/11. Today she works for Delta, earns top-of-scale pay, and chooses her monthly schedule based on her family’s needs, often dropping every assigned trip to rebuild the month from scratch.

She explains the hidden economics of flight attending—how pay is calculated, how to game the system, and why the swankiest layovers are hotly contested. Julieta also opens up about her family’s financial history: buying a $7,000 house, doing accidental landlording, weathering debt consolidation (twice), and how their motto became “spend less, don’t work more.”

We discuss how unschooling her kids changed everything—especially how she sees time, purpose, and money. She describes the shift from tiger mom to intentional parent, how her body reminds her when she’s over-pleasing, and why she’ll never again miss a family moment for the sake of someone else’s crisis at work.

We also get into her enduring love for bookstores, slow travel, and the trees of Michigan—and how she’s built a life that lets her say “no” to work, “yes” to crafting, and “maybe” to the chickens next door.

Full transcript: dirtbagrich.com/julieta

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

Blake Boles is a 42-year-old writer, cycle tourist, trail runner, partner dancer, and California-born temporary European expat who leads international trips for self-directed teenagers and young adults. (blakeboles.com)

In this special episode, former guest Jenny Abegg interviews Blake about what he's doing with his life, the Dirtbag Rich project, his early influences, and how he thinks about freedom, purpose, security, and more. Topics include:

• Freedom as “not being available for servitude”
• His view of long-term security and alternative retirement plan
• What the hard moments look like in a life on the road
• His undying love for the Deutschland Ticket (an unlimited travel pass covering all forms of public transport in Germany)
• How much stuff he actually owns (and the rules he sets for himself around possessions)
• Finding stability through extensive planning (and Google Calendar), and security through extensive friendships (his friend buckets include: dance, outdoors, college, and two summer camp communities)
• Why getting older is mostly awesome
• Who Dirtbag Rich is actually written for (and why it’s not 40/50/60-year-olds)
• His allergy to most "lifestyle" books (see: The 4-Hour Workweek) and how he's trying to do better
• The mysterious overlaps between unschooling, tiny houses, partner dance, love of wilderness, and the pursuit of dirtbag riches
• His biggest early influences: the Berkeley Student Cooperatives, Deer Crossing Camp, and Not Back to School Camp—yin and yang
• The magic of working your ass off, surrounded by people you deeply respect, in a beautiful natural environment
• How pointless school experiences led him to a deeper search for purpose, which he found in off-trail backpacking, reading alternative education theory, and independent foreign travel
• The flywheel of total aliveness, curiosity, enthusiasm, and positivity—and how keeping the flywheel going became his purpose
• What idolizing a dirtbag hiker (and failing to hike the Pacific Crest Trail) taught him at age 22
• His money situation
• How his life is currently not working

And finally, if you stick around to the very end: Jenny & Blake’s illicit scheme to create a "dark night of the dirtbag soul" OnlyFans.

Full transcript: dirtbagrich.com/blake

A quick update about the Dirtbag Rich podcast and book-in-progress.

Links:

• Dirtbag Rich: an update (The Adventures of Blake)
• Paul Millerd's episode appears on The Pathless Path
• Luke Mehall's episode appears on Dirtbag State of Mind
• Hike More, Work Less: the “Dirtbag Rich” Lifestyle (hiking-trails.com)

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