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 / @nursesinvestingforwealth

Full 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/)