Dirtbag Rich

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

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

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

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 planWhat the hard moments look like in a life on the roadHis 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 awesomeWho 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 betterThe mysterious overlaps between unschooling, tiny houses, partner dance, love of wilderness, and the pursuit of dirtbag richesHis biggest early influences: the Berkeley Student Cooperatives, Deer Crossing Camp, and Not Back to School Camp—yin and yangThe magic of working your ass off, surrounded by people you deeply respect, in a beautiful natural environmentHow 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 travelThe flywheel of total aliveness, curiosity, enthusiasm, and positivity—and how keeping the flywheel going became his purposeWhat idolizing a dirtbag hiker (and failing to hike the Pacific Crest Trail) taught him at age 22His money situationHow his life is currently not workingAnd 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 PathLuke Mehall's episode appears on Dirtbag State of MindHike 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

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 32-year-old outdoor photographer and climber who turned a summer job in Yosemite into a whole new life. (miyatsudome.com)She grew up in New York’s Hudson Valley, studied English, and had $30,000 in student loans when she decided to skip the New York City career path and head west. A one-way ticket to San Francisco led her to a service job in Yosemite Valley, where she earned $124 her first week—and got hooked on the lifestyle.Miya spent five years living and working in Yosemite, climbing, guiding, and building a life around the outdoors. She eventually picked up a camera, sold her first photos to Patagonia, and landed an internship that helped launch a career in adventure photography.Now based in Bishop, California, Miya splits her time between freelance photo and video work—often for outdoor brands and environmental nonprofits—and climbing as much as possible. Her low overhead and years of dirtbag training let her work every other day and climb the rest. She’s not chasing huge paychecks, but she is saving money and doing work that feels meaningful.We talk about the tension between freedom and financial insecurity, how her Japanese dad’s example shaped her sense of possibility, and how she still lives with the classic freelancer dread: “What if the phone stops ringing?”Full transcript: dirtbagrich.com/miya

Tracy and Andy Duncan are a couple living full-time aboard Another Summer, a boat they call home with their five children. (linktr.ee/SVanothersummer)Leaving behind suburban life in Atlanta, the Duncan family embraced a life of adventure, spending their days on the open water and learning to balance work, family, and self-sufficiency. Tracy shares how COVID pushed them to rethink their lifestyle, how their time together during the lockdown led to a deeper connection and a desire for more freedom, and how homeschooling was a natural fit for their children, particularly those with special needs.Living on a boat has its own set of challenges, from organizing a floating home with limited storage to managing basic repairs in a remote location. Andy and Tracy reflect on how their lives have become more organized than ever, driven by the necessity of dealing with the logistics of boat life—whether it’s finding the right part for a repair or packing food in small spaces. Their financial setup is unconventional, relying on adoption stipends for day-to-day expenses, while Andy’s remote IT work supports big-ticket items like boat repairs and upgrades.The Duncan family has found an unexpected rhythm in their nomadic life, with their children thriving in an environment where they have constant access to each other and the natural world (complete with “roving pirate gangs” of teenagers). Tracy talks about how their kids have formed tight-knit relationships not only with each other but also with the broader boat community, which is a small, interconnected world of its own. Andy and Tracy also share how they balance the close quarters of boat life with the need for individual space and reflection, and how their family’s adventures continue to shape their values and sense of connection.Full transcript: dirtbagrich.com/tracyandandy

Jonathan Kalan is a 37-year-old photojournalist-turned-entrepreneur who built his career reporting from the front lines of revolutions, refugee crises, and emerging tech scenes across Africa and the Middle East. (jonathankalan.com)Publishing in outlets like The New York Times and The Atlantic, he covered the sharp edges of globalization—until the stress, financial instability, and nonstop travel burned him out. Tired of chasing deadlines and scraping by on freelance checks, he walked away from journalism without a clear plan, except that he wanted more control over his life.That decision led to Unsettled, a company offering travel experiences designed for professionals who weren’t ready to settle into a single career, city, or routine. Jonathan describes the chaotic early days of launching the business—testing ideas in borrowed villas, running trips on razor-thin margins, and figuring out how to sell something as intangible as “structured uncertainty.” The demand was immediate, and Unsettled quickly expanded to destinations across Latin America, Europe, and Southeast Asia, attracting mid-career professionals looking for something between a vacation and a career change.But growth didn’t mean stability. Jonathan talks about the financial rollercoaster of running a business dependent on global travel, how the pandemic nearly destroyed everything overnight, and the brutal decisions he and his co-founder had to make to keep Unsettled alive. He breaks down the economics of the business—why they never took venture capital, how they priced trips to be profitable but accessible, and what it took to rebuild after their revenue went to zero in 2020.These days, Jonathan works as a startup consultant, helping founders navigate early-stage growth, branding, and business strategy. He shares how his experience building Unsettled shaped his approach to entrepreneurship, why he’s skeptical of venture-backed business models, and the biggest mistakes he sees new founders make. We also get into the time he nearly bought a failing surf lodge in Nicaragua, the strangest place he’s ever worked from, why "hustle culture is bullshit," and our shared experience of cycling the Carretera Austral in Patagonia.Full transcript: dirtbagrich.com/jonathan

Halle Homel is a 27-year-old outdoor guide, van dweller, and questioning nomad who built her life around travel, adventure, and seasonal work—and now asks herself whether the road still feels like home. (@halletreks)After graduating college a year early with a degree in creative writing, Halle hit the road in her Kia Soul and spent three months visiting all 48 contiguous states alone. That trip turned into six years of van life, guiding rock climbing, backpacking, and canoeing trips across the U.S. while living on public land and making seasonal wages stretch through the winter. But as she and her partner juggle life in a van with a six-day-a-week climbing schedule, the absence of a real home base is starting to feel more like survival mode than freedom.We discuss the economics of seasonal guiding: how she makes $200 a day on average, relies on tips for daily expenses, and stretches her summer paychecks to last all year. Halle shares the reality of van life in 2024, from Walmart parking lots to the mental toll of constantly moving, and why she’s now searching for a mountain town where she can return year after year. She also talks about breaking into the guiding world as a woman, the sexism she’s faced in climbing, and how she’s using her new Single Pitch Instructor certification to carve out a long-term career in outdoor leadership.She opens up about her evolving relationship with social media after going viral on TikTok, her role in environmental advocacy, and the tension between craving stability and chasing big, audacious goals—like summiting all 15 of California’s 14,000-foot peaks before October.Full transcript: dirtbagrich.com/halle

Daphné Robichaud is a 32-year-old outdoor travel leader who makes her living guiding hiking and biking trips across the world. (@thewanderingdaph)Daphné spends her summers leading back-to-back adventures in places like Patagonia, Iceland, and the French Alps: solving problems on the fly, adapting to new groups every week, and spending long days on trail. We talk about what it’s like to build a life around seasonal work, the thrill and exhaustion of constantly resetting with new teams, and how she structures her year to maximize both income and time off.Daphné breaks down the financial realities of trip leading: why she saves nearly 40% of her earnings despite an unpredictable schedule, how free housing and food change the equation, and why she feels more financially stable now than she did working a salaried government job.Earlier in her life, Daphné studied criminology and international development, struggled with anxiety throughout her 20s, and deeply questioned whether she was on the right path. Now she doesn’t worry about what comes next—just whether her next winter will be spent in the mountains or by the sea. Despite the constant movement, she’s found ways to maintain deep friendships and a committed relationship, proving that stability doesn’t have to come from staying in one place.Full transcript: dirtbagrich.com/daphne

Jenny Abegg is a 40-year-old mountain athlete, writer, and business co-founder who has built her life around spending extended time in the mountains. (@jabegg)Jenny describes how she went from a religious upbringing that emphasized self-denial and sacrifice to a life fully dedicated to climbing. She recalls the moment she left the church, the deep personal transformation that followed, and how moving into her van and chasing vertical adventure became her form of self-discovery.We discuss her evolution from mountaineering, to climbing, to her current obsession: long, technical mountain linkups in running shoes, where she combines her climbing background with ultra-distance endurance. Jenny reflects on why she’s more anxious in everyday life than when she's committing to an alpine traverse, the feeling of absolute freedom that comes from moving fast in the mountains, and what it’s like to be the "crazy lady in running shoes" on a glacier.We also get into the financial side of her dirtbag years—living in a van, earning just enough as a freelance writer and guide, and later using smart real estate moves to build long-term security. Jenny now co-runs BetterTrail, an outdoor gear review site that blends sustainability with practical advice.Finally, Jenny opens up about turning 40, grappling with the question of long-term purpose, and wondering what life will look like when her body no longer lets her run across the mountains she loves.Full transcript: dirtbagrich.com/jenny

Ed Gillis is a 49-year-old teacher, writer, and bike tourist who, along with his 44-year-old wife Jocelyn, has spent the last 16 years enjoying long cycle trips with their two sons. (yukon4explore.com)From hiking Patagonia with a newborn to biking 10,000 kilometers across Europe as a family of four, Ed breaks down how they made adventure a non-negotiable part of parenting. He shares how they kept the trips affordable—living without a car, cobbling together gear, and taking full advantage of the generosity of strangers. We discuss the financial trade-offs of choosing time over money, the long nights spent juggling freelance work and childcare, and how their Yukon-based careers as a teacher and naturopath allow them to take summers (and sometimes half-years) off for extended bike tours.Now that their teenage sons plan the routes and carry most of the gear, Ed jokes that his days of being the strongest rider are over. We also get into the magic of Warmshowers hosts, why New Zealanders love inviting traveling families into their homes, and what happens when your only roadtrip soundtrack is One Direction.Ed’s books, Bike Touring with Kids: the Oceania Odyssey and Bike Touring with Kids: the Europe Epic, document the family’s adventures.Full transcript: dirtbagrich.com/ed

Artec Durham is a 39-year-old ICU nurse, property investor, and former dirtbag who only works two shifts a month—and still manages to cover his living expenses through strategic real estate choices. (@artec_rn)Artec shares his unconventional path, from a childhood spent unschooling, guiding wilderness trips, and discovering a passion for nursing through wilderness medicine. He breaks down how he buys fixer-uppers and turns them into rental income, with YouTube as a teacher. Today he maintains his properties with just a few days of work each year, spends his summers hosting outdoor athletes at his Colorado property, and uses his time for adventures like bikepacking across Death Valley and packrafting the Grand Canyon. His primary vehicle is a totaled minivan, which he uses to retrieve abandoned building supplies from the side of the road.We discuss the thrill and toll of ICU nursing, why Artec never wants full-time employment again, and how his dirtbag upbringing led to a lifelong commitment to maximizing freedom and community over traditional metrics of success. Artec also opens up about how pushing his physical limits through ultra-distance bike races led to heart complications, forcing him to reconsider intensity and refocus on connection, community, and the joy of playing outside.Full transcript: dirtbagrich.com/artec

Emily Pennington is a 37-year-old freelance writer, former Hollywood assistant, and full-time outdoor nerd who once lived in a minivan for a year to visit every U.S. national park. (@brazenbackpacker)In her 20s, Emily bounced between creative careers—first as an actress, then as a circus performer, then as a film producer’s assistant. The job paid okay, but the work felt meaningless, and after losing several friends to sudden deaths, she started questioning the whole plan. She cut her expenses, saved aggressively, and quit in 2020 to hit the road full-time.That trip, which started as an attempt to reboot her life, turned into a book (Feral) and a new career as a freelance adventure writer. But the realities of making a living as a writer are far from glamorous. Emily breaks down exactly how much she made from her Outside Magazine column and book advance, how she cobbles together an income from travel writing and gear reviews, and why she still occasionally wonders if the whole industry will collapse. Emily also discussed the burnout of monetizing your passions, the constant anxiety of freelance work, and how she preserves time for hikes that aren’t “content.”Now based in Boulder, Colorado, she’s finally settled into a routine that gives her the freedom she was looking for—working Monday to Thursday, keeping her weekends sacred, and skiing in the middle of the week whenever she wants. And because she can’t stop picking up new creative projects, she’s also fronting a folk-punk band called Trouble's Braids.Full transcript: dirtbagrich.com/emily

David Six is a 40-something-year-old software developer, Triple Crown thru-hiker, and lifelong travel addict who has spent the last two decades figuring out how to work as little as possible while hiking, biking, and exploring the world. (@walkacrossoregon)David breaks down how he built a life that lets him disappear into the wilderness for months at a time without running out of money. He explains how he went from high school drop-out to self-taught programmer, how he co-founded a ticket sales software company that now funds his adventures, and why he sometimes mails himself a laptop just to keep his business running while on trail. Unlike most thru-hikers, who treat long-distance hiking as a one-time adventure, David turned it into an ongoing way of life, balancing the need for income with his desire to spend as much time as possible moving through the world under his own power.We discuss what draws people to thru-hiking, why long hikes feel like time travel, and the transition shock that hits hard when the journey is over. David reflects on his anti-authority streak, his deep-seated resistance to full-time work, and why, despite having a near-perfect job setup, he still resents it. He also shares how he and his wife (a nurse) use travel hacking and careful planning to fund their adventures, including multiple round-the-world trips.Finally, David talks about his next big project: walking across the entire state of Oregon, from the Pacific Coast to the Idaho border, in the middle of winter.Full transcript: dirtbagrich.com/david

Adrianna Nine is a 28-year-old freelance writer, newsletter author, and desert enthusiast who once traded freedom for a high-paying corporate job—and lived to regret it. (adriannanine.com)Adrianna breaks down her escape from corporate trust and safety, where she made great money but had no time to spend it, except on gadgets and overpriced appetizers. She describes hitting rock bottom, ignoring everyone who told her writing wasn’t a real career, and slowly building a life of creative independence.Adrianna does freelance tech and science writing, as well as running a boutique copywriting agency. She averages 25 hours of work per week—leaving plenty of time for baking, gym sessions, desert conservation work, and personal writing projects, including a novel in progress. We get into financial habits that made her transition possible, the realities of self-employment, and why she feels more secure juggling multiple clients than working a single full-time job.We also discuss her deep love for the Arizona desert, the tattoos to prove it, and how a coyote made her cry in Joshua Tree. She talks about the themes of her newsletter, Creativity Under Capitalism: protecting your time, resisting the urge to monetize everything, and creating what matters.Full transcript: dirtbagrich.com/adrianna

Paul Millerd is a 39-year-old writer, ex-consultant, and advocate for ditching the default path in favor of what he calls “the pathless path.” (pmillerd.com / @p_millerd)Paul walked away from a promising corporate consulting career—think McKinsey, prestige, and six-figure salaries—to pursue a life of writing, experimenting, and global wandering. He describes how he initially struggled with unlearning his achievement-oriented mindset, why the idea of good work (work that energizes) became his guiding principle, and how his first self-published book, The Pathless Path, briefly and unexpectedly earned six figures.We discuss the philosophical basis of work and money, how to avoid the traps of both scarcity and overachievement, and how the value of exercising your freedom is limited by how others exercise their own freedom. (In other words: if you're free to hike on a sunny Wednesday afternoon, and no one's available to go with you, are you really free?)Paul and his wife have a young daughter, and they struggle to find and live near other, like-minded families. We talk about how online communities help Paul stay connected while living nomadically between Texas and Taiwan and how online self-education was invaluable to his success. We conclude with a discussion of navigating fear and uncertainty on the pathless path.Throughout the conversation, Paul stays refreshingly honest about the tensions between freedom and stability, the allure of easy money, and the ever-present temptation to fall back into old habits of achievement and validation. Energized by this conversation, I ended up talking more than usual about the tricky balance of factors that leads to a Dirtbag Rich existence. Full transcript: dirtbagrich.com/paul

Emma Hayward is a 30-year-old sailor who splits her time between an Antarctic research vessel, Rhode Island, and living on a boat that she fixed up. (@emmastoryhayward)Growing up on Cape Cod with parents who worked on boats, Emma never wanted an office job or predictable life—which is why she keeps building a life at sea, even as her friends settle down and start families.Emma describes her journey from a “schooner bum” to a dirtbag rich captain and boat owner who works 3-4 months/year to cover her costs and accumulate savings. Crucial to this journey was securing a position on a 300-foot Antarctic research vessel, where she launches scientific gear as part of climate-related projects.How do people make money with boats? Emma walks us through the options, from crewing fancy yachts (lucrative but not so purposeful) to charter day-trips (lucrative and somewhat purposeful) to outdoor education on tall ships (very purposeful but horribly paid). She touches on power and gender dynamics at sea, dealing with boredom and monotony, and the challenge of maintaining friendships and romantic partnership when spending so much time away.Emma also tells the story of her gap year (and a half) when she sailed from Hawaii to San Diego with her dad, as well as a recent voyage from Rhode Island to Ireland that ended with a week of dodging container ships amid thick fog.Full transcript: dirtbagrich.com/emma

Tim and Angel Mathis are married nurses and lapsed Christians who enjoy hiking, running, and traveling very long distances. Tim is the author of The Dirtbag's Guide to Life (timmathiswrites.com) and Angel teaches investment skills to fellow nurses (learn.nursesinvesting.com).Tim begins by sharing his feelings about me stealing the term "dirtbag rich"—which he coined in his 2019 book—and transforming it into a larger concept that emphasizes purposeful work.Tim finds his own purpose as a mental health nurse and book writer. He tells the story of losing his dad in the middle of a Pacific Crest Trail hike, the period of hedonistic dirtbag drifting that followed, and how he went from evangelical Christian, to Episcopal minister, to fully leaving the faith. He describes how ultrarunning and thru-hiking offered a quasi-religious new community, sense of belonging, and positive emotions. "Nature is my spirituality now," Tim says—and this is a "deeply American thing."We then hear from Angel—the financial brain in the marriage—who shares the story of getting laughed at by a financial advisor early in their careers. The couple ended up doing everything the advisor didn't think possible: buying a house, getting graduate degrees, making work optional after age 35, and traveling 3-6 months each year.Angel's sense of financial security comes from taking a hard look at the numbers each month, using the same method that she teaches to other nurses. As a nurse practitioner, she enjoys helping many patients in a short amount of time—just as long as she's working part-time. Raised Catholic and later baptized Protestant, Angel laughs about enjoying a diversified spiritual portfolio, even as nature-oriented rituals have replaced the religious ones (e.g., long runs on Sundays instead of church). She reflects on how easy it was to build new friendships in their thirties through long-term traveling hiking, where low time pressure allows deep relationships to blossom.Find Tim and Angel on Instagram: @dirtbagguide / @nursesinvestingforwealthFull transcript: dirtbagrich.com/timangel

Justin Riley is a 40-year-old dance teacher, wilderness junkie, and organizer of alternative-culture partner dance events. (justindance.com)Justin has spent nearly two decades designing events that blur the line between art, dance, and wilderness immersion. His festivals are more than just places to dance—they’re cultural experiments that challenge people to step outside their comfort zones and co-create something meaningful. Whether it’s a week-long floating dance party on Utah’s Green River or a countryside retreat in Spain, Justin’s spaces are deliberately messy and wildly participatory. (He’s also responsible for helping me fall in love with fusion dance in 2016.)We discuss Justin’s early years as a dirtbag wanderer living on $5,000 a year while chasing dreams as a photojournalist and political activist and the joy he finds in solving life’s problems without money. Today he earns money through a combination of event organizing, dance teaching, and converting buses and vans. When work feels so much like play, Justin observes, “I feel like my whole life is filled with free time.”Justin explains his "high risk, low consequence" design philosophy, his commitment to wilderness exploration (a vital counterbalance to his hyper-social work), and his belief that meaningful experiences don’t come from perfection but from trust, collaboration, mutual joy, and the willingness to let things break—and then building something new together.Find Justin’s next events at unboundfusion.com.Full transcript: dirtbagrich.com/justin

Victoria Bruce is a 39-year-old writer, adventurer, and single mom who hiked New Zealand’s 3,000-kilometer Te Araroa trail with her seven-year-old daughter, Emilie. (@adventures_with_emilie)Victoria’s journey stemmed from a desperate need to escape the crushing stress of city life and heal from complex post-traumatic stress disorder, a legacy of her difficult childhood. Through six months of hiking, she discovered a deeper connection with her daughter, her country’s wild landscapes, and herself.We discuss the physical and emotional trials of walking the length of New Zealand, including nights spent battling windstorms and Emilie’s determination to hike 30 kilometers for the promise of ice cream. Victoria reflects on the economic and lifestyle trade-offs that allowed her to make this leap, and how hiking transformed her parenting, career, and mental health.Victoria shares her post-trail life, including her move to a 100-year-old cottage on New Zealand’s west coast, a part-time freelance writing career, and ambitious new goals like thru-hiking the Continental Divide Trail. She also opens up about her unconventional and challenging young adulthood, navigating foster care and addiction recovery.Finally, we explore the delicate balance of adventuring as a parent: considering your child’s needs, avoiding the pitfalls of neglect, and embracing a lifestyle that prioritizes time, connection, and wilderness over material wealth.Victoria’s award-winning book is Adventures with Emilie, available everywhere.Full transcript: dirtbagrich.com/victoria

Alastair Humphreys is a 47-year-old British adventurer, author, and speaker who has cycled around the world, rowed across the Atlantic, busked with a violin across Spain, and made a career from telling his stories and encouraging others to live more adventurously (alastairhumphreys.com).Alastair talks about the “push” and “pull” factors that drive certain people toward lives of wanderlust and adventure. At age 24, he couldn’t imagine becoming a science teacher and decided to embark upon a very long bike trip instead. Four years later, his round-the-world cycle tour only deepened his thirst for adventure, prompting him to turn it into a career: one he sustains through writing, speaking, filmmaking, podcasting, and brand sponsorships.What motivates Alastair? Initially, it was the desire to make the most of life—it drove him crazy to see how many privileged people squandered their opportunities. Now he’s less manic and more fired up about thorny environmental problems. Most consistent is Alastair’s “complete aversion to a high-stress life.”Is adventure only for privileged people? Alastair takes a nuanced position, both admitting the reality and encouraging a proactive, opportunity-focused mindset. He also discusses how adventures are different from vacations—because they necessarily involve uncertainty, risk, and discomfort—but emphasizes that they come in all sizes, and it’s not useful to compare your own adventures to those of others.In the early 2000s, Alastair scraped together £7000 for his round-the-world trip and made it last for four full years by living like a total dirtbag. He then set himself a goal of earning as much from adventure as he might as a teacher. Now that he’s achieved a reliable income, he works less and spends more time as a stay-at-home dad. Eventually he hopes to earn his living entirely from writing.Alastair’s passions have mellowed with age, but he still finds himself yearning for raw, uncertain adventure at times: impulses that he channels into a curiosity for his local area (a “mundane, suburban corner of England”) and discovering unexpected pockets of wildness and solitude. His advice for adventure-curious young people is almost always “Go!”, even if it doesn’t make sense or fit neatly into a life plan.Spiritually, Alastair describes growing up Christian-curious but finding “no evidence of higher powers” on his cycle journey. Now he’s an atheist with a deep interest in awe, grace, and mystery.Find Alastair Humphreys on every online platform except TikTok. He’s currently finishing up a children’s book about the Lewis & Clark expedition.(I was looking forward to interviewing Alastair for a very long time. You may detect this in my gushing praise and rambling questions.)Full transcript: dirtbagrich.com/alastair

Russell Max Simon is a 42-year-old climber, marketer, and “post-nomad” who splits his time between a derelict house in Spain and an old farmhouse in New Hampshire. (russellmaxsimon.com)After living many years as a digital nomad, Russell settled down in New Hampshire during the pandemic and rediscovered the virtues of place and community. Now he owns (and constantly renovates) two old properties, each strategically located next to prime climbing areas, where he plays host to the dirtbag climbers who reliably arrive each season.We discuss Russell’s early career in Washington, D.C., his work in politics and environmental advocacy, and his gradual loss of community and purpose. Now his days consist of reading and writing in the mornings, climbing and building in the afternoons, and spending time with friends and family in the evenings. To pay the bills, Russell does 5-10 hours of content marketing per week.Although he no longer seeks meaning from his paid work, Russell appreciates the clarity and honesty of his freelance gigs and how they empower him to do what he loves, be close to his people, and support the climbing community. He explains why he’s careful to not earn too much, how he says “no” to his clients, and why he doesn’t try to expand his business.Russell emphasizes how digital nomads consistently “over-index on freedom” and neglect the importance of deeper friendships and relationships. He shares how the climbing and kitesurfing communities offer such depth to him, and how merging one’s love life with an activity group presents both threats and delights. Russell is also the father of a 14-year-old son, and we discuss how his dual-continent, climbing-focused life intersects with his role as a co-parent.Finally, Russell shares one of the big reasons he adores southern Europe: sitting outside with friends at a cafe or bar for multiple hours is completely normal.Russell’s excellent newsletter is Post-Nomad.Full transcript: dirtbagrich.com/russell

Kelsey Shipman is a 39-year-old writer, mom, former teacher, and ambivalent expat living in San Miguel de Allende, Mexico, while escaping the heat, politics, and high cost of her home state of Texas. (kelseyshipman.com / @kelseyerinshipman)Kelsey is the weirdo world traveler from an otherwise conventional Texas family who ended up living in Ghana, Bolivia, the Czech Republic, and Uzbekistan over the course of two decades. Now she’s come to accept that living abroad is key to “doing her life’s work” and raising her young daughter with sanity.Kelsey mostly works as a ghostwriter, focused on memoirs and cookbooks. Her husband does remote IT work and schoolteaching. Together they work a combined 40-50 hours a week and earn $5-6k/month, which is more than enough to live well in a beautiful, expat-friendly city in Mexico. Previously they were earning twice that in Austin, Texas, where they lived on the city outskirts, drove everywhere, and felt deep financial stress.Finding affordable, high-quality childcare in Mexico changed everything. Previously they paid $1300/month to send their daughter to a preschool in Austin that didn’t even cover the full day. Now, their daughter goes to a preschool within walking distance and has a wonderful, caring nanny.We discuss the ethics of living abroad, bringing US dollars into lower-income countries, and contributing to the cultural change that rapidly transforms places like San Miguel de Allende. Kelsey reveals the irony that while she may be “part of the problem,” she and her husband were also priced out of Austin by Californians who migrated there during the pandemic.Finally, Kelsey offers advice for behaving well as an expat—namely, keeping your voice down and not talking about “how cheap everything is.”Kelsey’s Substack is White People School (https://kelseyshipman.substack.com/)

Suzanne Roberts is a 54-year-old travel writer, memoirist, educator, and lifelong ski bum. (suzanneroberts.net) Ever since quitting her full-time job at 47, Suzanne Roberts has written books, published poetry, traveled the world, and skied every winter while living off a modest income with her semi-retired husband. We discuss Suzanne’s decision to not have kids, growing up with a family tradition of guilt, and her firm belief that education is the path to freedom. She talks about leaving her first marriage after realizing that her partner didn’t share her passion for long-term travel and backcountry skiing, how she built a life around friendship, and the appeal of quirky mountain towns (like South Lake Tahoe, California, where both she and I have lived) for those taking unconventional life paths. Suzanne openly discusses her recent brain tumor diagnosis, how it factors into her travel and outdoor pursuits, and why “safety is a superstition” that shouldn’t stop you from doing what you love. Finally, she names the many female travel and adventure writers who have inspired her own path. Suzanne’s Substack is 52 Writing Prompts. Shout-out to Lauren Lindley (@laurenlindleyphoto) for connecting us. Full transcript: dirtbagrich.com/suzanne

Hannah Bowley is a 32-year-old speech-language pathologist in Seattle who recently cycled across the world for a year and plans to do something similar every three years. (@hannahbowley) Hannah and I met when she hosted me, as a total stranger, at her apartment in Seattle. We later embarked upon a 5-week cycle adventure in Patagonia, where we experienced stunning landscapes, challenging gravel roads, and a shocking lack of empanadas. This was just one of many adventures for Hannah, who was in the middle of a 11-month cycling voyage through Europe, South America, and Asia. To make this trip possible, Hannah lived super frugally in Seattle—a superpower in itself—and took advantage of a hidden clause in her public school contract, allowing her to take a full year of unpaid time off every three years. She discusses the mental journey of long-term travel, how she convinced friends to join her along the way, the kindness of strangers, and how she relaxed about money throughout the trip. (She spent a grand total of $23,000, including flights.) Hannah considered recruiting a full-time travel partner, but she ultimately chose to go solo as a form of personal growth, becoming less obsessed with time and embracing her introversion. Back home in Seattle, Hannah enjoyed her 9-to-5 existence before the trip but couldn't see herself taking the next big steps that her friends were taking (house, marriage, kids). After the trip, she's still trying to find a new normal, struggling with an excess of consumer choice, and may be experiencing an existential crisis. We conclude with a discussion of our mutual friend and adventure partner, Vince, and how the three of us formed a lean, mean, Patagonia cycling team... even when the horseflies arrived. Full transcript: dirtbagrich.com/hannah

Brendan Leonard is a 45-year-old writer, illustrator, ultramarathon runner, new father, and former dirtbag who makes a living by sharing his love for the outdoors. (semi-rad.com / @semi_rad) After spending many years focused on running, climbing, skiing, cycling, hiking, and traveling, Brendan Leonard has settled down in Montana with his wife and young son. He explains the original meaning of the word "dirtbag," what his own dirtbag phase looked like, and how he cobbled together a multifaceted creative career in which he essentially gets paid to "go out, do interesting things, come back, and write about them." We discuss the nuances of making money from your hobbies, why Brendan tells stories of everyday adventure rather than epic expeditions, and his favorite way to measure his impact. He explains how having a child changed his life in deeply meaningful and entirely predictable ways, where exactly his money comes from, and how he and his wife (also a freelancer) managed to buy a house in a cute university town in Montana without family assistance. Brendan concludes by defining the core ethos of dirtbagging: enjoying the freedom to wake up each day and decide what you're going to do with your day—and by extension, your life. I highly recommend Brendan's most recent book, "Ultrasomething," and his "Friday Inspiration" newsletter. Full transcript: dirtbagrich.com/brendan

Brittany Goris is a 31-year-old nomad who lives in her van, works 15 hours a week doing graphic design, and spends the rest of her time as a professional rock climber. (brittanygoris.com / @gorisb) We discuss what Brittany learned from witnessing bankruptcy as a child, the guilt she feels when eating at restaurants, how her life truly began when she moved into her car, and the deep sense of belonging she feels among like-minded misfits in the climbing world. Much like me, Brittany feels listless whenever she stays in one place longer than three months; then she moves, and everything gets better. As a child, Brittany's dad nudged her toward a more high-achievement path, while her mom was an artistic dreamer—a combination she believes led to her ability to simultaneously manage money and live a passion-centered life. While Brittany has plenty of savings and pays her own way as an adult, she also acknowledges that her family safety net (which would provide a place to stay if she ever gets sick or injured) enables her lifestyle. Brittany observes how difficult it can be to sustain the dirtbag climber lifestyle over the long haul. Whether you’re a high-paid tech worker or a low-paid seasonal worker, stress and burnout are real threats, and maintaining romantic relationships is challenging. In the past, Brittany worried about whether she’d have a good social life on the road and if she could survive a vehicle breakdown in the middle of nowhere. Now, she doesn’t worry about either. Beyond her fully remote graphic design work, Brittany earns a little money from climbing sponsorships, public speaking, teaching climbing clinics, and working at a rock gym. Full transcript: dirtbagrich.com/brittany

What's this podcast about? What's a dirtbag, and what does it mean to be dirtbag rich? Who will you hear from, and what will we discuss? And if you followed me here from the alternative education world—what's the connection? So many questions, and so many answers. Welcome to Dirtbag Rich. Video & transcript: dirtbagrich.com/intro