Dirtbag Rich

Suzanne Roberts is a 54-year-old travel writer, memoirist, educator, and lifelong ski bum. (suzanneroberts.net) Ever since quitting her full-time job at 47, Suzanne Roberts has written books, published poetry, traveled the world, and skied every winter while living off a modest income with her semi-retired husband. We discuss Suzanne’s decision to not have kids, growing up with a family tradition of guilt, and her firm belief that education is the path to freedom. She talks about leaving her first marriage after realizing that her partner didn’t share her passion for long-term travel and backcountry skiing, how she built a life around friendship, and the appeal of quirky mountain towns (like South Lake Tahoe, California, where both she and I have lived) for those taking unconventional life paths. Suzanne openly discusses her recent brain tumor diagnosis, how it factors into her travel and outdoor pursuits, and why “safety is a superstition” that shouldn’t stop you from doing what you love. Finally, she names the many female travel and adventure writers who have inspired her own path. Suzanne’s Substack is 52 Writing Prompts. Shout-out to Lauren Lindley (@laurenlindleyphoto) for connecting us. Full transcript: dirtbagrich.com/suzanne

Hannah Bowley is a 32-year-old speech-language pathologist in Seattle who recently cycled across the world for a year and plans to do something similar every three years. (@hannahbowley) Hannah and I met when she hosted me, as a total stranger, at her apartment in Seattle. We later embarked upon a 5-week cycle adventure in Patagonia, where we experienced stunning landscapes, challenging gravel roads, and a shocking lack of empanadas. This was just one of many adventures for Hannah, who was in the middle of a 11-month cycling voyage through Europe, South America, and Asia. To make this trip possible, Hannah lived super frugally in Seattle—a superpower in itself—and took advantage of a hidden clause in her public school contract, allowing her to take a full year of unpaid time off every three years. She discusses the mental journey of long-term travel, how she convinced friends to join her along the way, the kindness of strangers, and how she relaxed about money throughout the trip. (She spent a grand total of $23,000, including flights.) Hannah considered recruiting a full-time travel partner, but she ultimately chose to go solo as a form of personal growth, becoming less obsessed with time and embracing her introversion. Back home in Seattle, Hannah enjoyed her 9-to-5 existence before the trip but couldn't see herself taking the next big steps that her friends were taking (house, marriage, kids). After the trip, she's still trying to find a new normal, struggling with an excess of consumer choice, and may be experiencing an existential crisis. We conclude with a discussion of our mutual friend and adventure partner, Vince, and how the three of us formed a lean, mean, Patagonia cycling team... even when the horseflies arrived. Full transcript: dirtbagrich.com/hannah

Brendan Leonard is a 45-year-old writer, illustrator, ultramarathon runner, new father, and former dirtbag who makes a living by sharing his love for the outdoors. (semi-rad.com / @semi_rad) After spending many years focused on running, climbing, skiing, cycling, hiking, and traveling, Brendan Leonard has settled down in Montana with his wife and young son. He explains the original meaning of the word "dirtbag," what his own dirtbag phase looked like, and how he cobbled together a multifaceted creative career in which he essentially gets paid to "go out, do interesting things, come back, and write about them." We discuss the nuances of making money from your hobbies, why Brendan tells stories of everyday adventure rather than epic expeditions, and his favorite way to measure his impact. He explains how having a child changed his life in deeply meaningful and entirely predictable ways, where exactly his money comes from, and how he and his wife (also a freelancer) managed to buy a house in a cute university town in Montana without family assistance. Brendan concludes by defining the core ethos of dirtbagging: enjoying the freedom to wake up each day and decide what you're going to do with your day—and by extension, your life. I highly recommend Brendan's most recent book, "Ultrasomething," and his "Friday Inspiration" newsletter. Full transcript: dirtbagrich.com/brendan

Brittany Goris is a 31-year-old nomad who lives in her van, works 15 hours a week doing graphic design, and spends the rest of her time as a professional rock climber. (brittanygoris.com / @gorisb) We discuss what Brittany learned from witnessing bankruptcy as a child, the guilt she feels when eating at restaurants, how her life truly began when she moved into her car, and the deep sense of belonging she feels among like-minded misfits in the climbing world. Much like me, Brittany feels listless whenever she stays in one place longer than three months; then she moves, and everything gets better. As a child, Brittany's dad nudged her toward a more high-achievement path, while her mom was an artistic dreamer—a combination she believes led to her ability to simultaneously manage money and live a passion-centered life. While Brittany has plenty of savings and pays her own way as an adult, she also acknowledges that her family safety net (which would provide a place to stay if she ever gets sick or injured) enables her lifestyle. Brittany observes how difficult it can be to sustain the dirtbag climber lifestyle over the long haul. Whether you’re a high-paid tech worker or a low-paid seasonal worker, stress and burnout are real threats, and maintaining romantic relationships is challenging. In the past, Brittany worried about whether she’d have a good social life on the road and if she could survive a vehicle breakdown in the middle of nowhere. Now, she doesn’t worry about either. Beyond her fully remote graphic design work, Brittany earns a little money from climbing sponsorships, public speaking, teaching climbing clinics, and working at a rock gym. Full transcript: dirtbagrich.com/brittany

What's this podcast about? What's a dirtbag, and what does it mean to be dirtbag rich? Who will you hear from, and what will we discuss? And if you followed me here from the alternative education world—what's the connection? So many questions, and so many answers. Welcome to Dirtbag Rich. Video & transcript: dirtbagrich.com/intro