James Brown is a 43-year-old traveler, relational coach, graphic designer, and lifelong seeker caught between the urge to roam and the desire to put down roots. (jameswonders.uk)After spending his twenties and early thirties working long hours in England’s gray corporate offices—commuting three hours a day to a job he genuinely loved but a life that left him drained—James finally broke free. He quit, bought a motorbike, and rode across Europe before taking an eight-month cycling journey through Asia with his girlfriend. The trip ended their relationship but sparked something else: a realization that he could live on very little, work remotely, and make his own rules.In the years that followed, James built a flexible, purpose-driven life as a freelance designer for nonprofits while living in Italy, Costa Rica, Spain, Morocco, and Colombia. His days alternated between deep creative focus and drifting—renting apartments in tiny towns, learning new languages, and building communities he would inevitably have to leave when visas expired or restlessness returned.At the heart of James’s story is tension: between adventure and stability, freedom and belonging. He dreams of having a home base, a dog, and his own cupboard full of clothes—but he also knows that at any moment, he could sell everything and ride into the horizon again. Lately he’s been trying to understand why through the practices of "circling" and "authentic relating."We talk about how childhood restlessness can become adult wanderlust, how travel can be both healing and escapist, and how to know when "freedom" starts to look like avoidance. James reflects on the comfort of drifting, the fatigue of constant choice, and what it might take to finally stop moving—not because he’s trapped, but because he’s ready to stay.Full transcript: dirtbagrich.com/james
--------
1:15:00
--------
1:15:00
Aisha Trent: seasonal worker, minimalist, car dweller
Aisha Trent is a 31-year-old seasonal worker, minimalist, and car dweller who’s spent the past two and a half years living out of her Toyota 4Runner—and doesn’t see herself going back. (@norent_trent)After losing both parents in a tragic car accident, Aisha decided life was too short to wait for permission. She downsized everything she owned, traded a Ford Fiesta for a 4Runner, and built a life centered on nature, healing, and independence. Now she sprays invasive weeds and algae from boats and shorelines each summer in Illinois, saving enough to take winters off for time with friends, or more recently, long solo road trips through Colorado, Oregon, and Arizona.We talk about why she prefers waking up surrounded by windows instead of walls, and how she and her boyfriend make “driveway living” work. Aisha also reflects on growing up insecure, her time in eating disorder treatment, and how outdoor simplicity became her therapy.She’s currently considering a short return to full-time work—just long enough to pay off her student loans and car debt and buy back even more freedom. But first she'll be collecting her inaugural passport stamps in Austria and the Philippines.Aisha's favorite quote: “It’s all lies. Back to nature—the only truth.” (from the music producer Rick Rubin)Full transcript: dirtbagrich.com/aisha
--------
57:27
--------
57:27
Diana Grijalva: climber, guide, dirtbag royalty
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
--------
1:03:46
--------
1:03:46
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
--------
53:39
--------
53:39
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
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