Dirtbag Rich

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

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

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

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

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