Kaya Lindsay is a 33-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