Dirtbag Rich

Blake Boles
Dirtbag Rich

How do you build a life of freedom, travel, nature, and meaningful work? Join author Blake Boles (blakeboles.com) as he dives deep with working adults who have managed to strike that elusive balance of time, money, and purpose—without giving up on their wildest dreams. These vulnerable and provocative conversations reveal how everyday people create lives filled with wilderness adventure, creative expression, frequent exploration, and financial stability—no trust fund required. Each guest shares their unique flavor of "dirtbag rich": a way of living that prioritizes time wealth, personal relationships, and transformative experiences over luxury, comfort, and excess security. ("Dirtbag" is a badge of honor in climbing and hiking communities, describing someone so devoted to their passion that they trade conventional success for the chance to do what they love, full-time.) Visit dirtbagrich.com for full transcripts and updates on Blake's forthcoming book, Dirtbag Rich: Low Income, High Freedom, Deep Purpose.

Episodios

  1. Alastair Humphreys: author, father, round-the-world cyclist

    HACE 4 DÍAS

    Alastair Humphreys: author, father, round-the-world cyclist

    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

    57 min
  2. Russell Max Simon: climber, marketer, post-nomad

    15 DIC

    Russell Max Simon: climber, marketer, post-nomad

    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

    1 h y 8 min
  3. Kelsey Shipman: expat, ghostwriter, mom

    8 DIC

    Kelsey Shipman: expat, ghostwriter, mom

    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/)

    51 min
  4. Suzanne Roberts: writer, teacher, ski bum

    1 DIC

    Suzanne Roberts: writer, teacher, ski bum

    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

    49 min
  5. Hannah Bowley: long-term cyclist, public school educator

    24 NOV

    Hannah Bowley: long-term cyclist, public school educator

    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

    55 min
  6. Brendan Leonard: writer, runner, father, ex-dirtbag

    17 NOV

    Brendan Leonard: writer, runner, father, ex-dirtbag

    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

    1 h y 12 min
  7. Brittany Goris: climber, nomad, graphic designer

    10 NOV

    Brittany Goris: climber, nomad, graphic designer

    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

    59 min
  8. Introducing: Dirtbag Rich

    1 NOV

    Introducing: Dirtbag Rich

    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

    12 min

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How do you build a life of freedom, travel, nature, and meaningful work? Join author Blake Boles (blakeboles.com) as he dives deep with working adults who have managed to strike that elusive balance of time, money, and purpose—without giving up on their wildest dreams. These vulnerable and provocative conversations reveal how everyday people create lives filled with wilderness adventure, creative expression, frequent exploration, and financial stability—no trust fund required. Each guest shares their unique flavor of "dirtbag rich": a way of living that prioritizes time wealth, personal relationships, and transformative experiences over luxury, comfort, and excess security. ("Dirtbag" is a badge of honor in climbing and hiking communities, describing someone so devoted to their passion that they trade conventional success for the chance to do what they love, full-time.) Visit dirtbagrich.com for full transcripts and updates on Blake's forthcoming book, Dirtbag Rich: Low Income, High Freedom, Deep Purpose.

Información

  • Creador
    Blake Boles
  • Años de actividad
    2 k
  • Episodios
    8
  • Clasificación
    Apto
  • Mostrar sitio web
    Dirtbag Rich

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