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?