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
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Julieta Duvall: flight attendant
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
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Michael Hughes: whitewater guide
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
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Jack Schott: summer camp lifer
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
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Morgan Sjogren: writer, desert rat
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
How do you build a life of freedom, travel, nature, and meaningful work?Join author Blake Boles (blakeboles.com) as he dives deep with working adults who have managed to strike that elusive balance of time, money, and purpose—without giving up on their wildest dreams.These vulnerable and provocative conversations reveal how everyday people create lives filled with wilderness adventure, creative expression, frequent exploration, and financial stability—no trust fund required.Each guest shares their unique flavor of "dirtbag rich": a way of living that prioritizes time wealth, personal relationships, and transformative experiences over luxury, comfort, and excess security.("Dirtbag" is a badge of honor in climbing and hiking communities, describing someone so devoted to their passion that they trade conventional success for the chance to do what they love, full-time.)Visit dirtbagrich.com for full transcripts and updates on Blake's forthcoming book, Dirtbag Rich: Low Income, High Freedom, Deep Purpose.
New Zealand