Dirtbag Rich

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/)