Episode 146 | Dirtbag Rich with Blake Boles
Episode Summary
Ryan Jordan interviews Blake Boles, author of Dirtbag Rich, about redefining wealth through time, purpose, flexibility, and outdoor freedom. They explore dirtbag culture, careers, housing, relationships, risk, and the pursuit of a life built around adventure, simplicity, and meaningful time outside before retirement.
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Show Notes:
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If you crave nature, freedom, adventure, and work that matters—rather than just paying the bills for a life you never chose—then you might be ready to become dirtbag rich.
Drawing from the “dirtbag” tradition of pursuing outdoor bliss through creative self-sufficiency, this book charts an unconventional way of living that includes both security and flexibility, connection and independence, and service and self-actualization.
Whether you’re jettisoning a life that’s not working or just getting started, the message of Dirtbag Rich is clear: You don’t have to play the same game as everyone else. You can have a life where you wake up and decide what you want to do, every day. You really can.
Through personal stories and candid interviews with people who’ve made it work—from nurses and trail runners to graphic designers and relationship coaches—Blake Boles shows how to build a life rich in time, purpose, and freedom.
Main Topic Bullets
- The historical meaning of “dirtbag” in climbing, thru-hiking, and outdoor culture
- How dirtbag culture has traditionally balanced freedom, poverty, adventure, and insecurity
- Blake Boles’ definition of the “Dirtbag Rich” lifestyle
- Why time, money, and purpose should be treated as coequal forms of wealth
- The difference between traditional financial wealth and time wealth
- How outdoor adventure changes the way people think about work, money, and lifestyle design
- Why many people defer freedom, travel, and outdoor experience until retirement
- The role of career flexibility in creating more time for hiking, backpacking, climbing, cycling, and travel
- How living in outdoors-oriented towns can support a lower-overhead, higher-adventure lifestyle
- The risks and trade-offs of choosing flexibility over conventional career advancement
- Housing strategies that support a dirtbag-rich lifestyle, including roommates, small homes, van life, travel, and shared living
- How cultural expectations around home ownership, status, and consumption shape lifestyle decisions
- The relationship between simplicity, minimalism, and freedom in both backpacking and everyday life
- Why relationships, community, and the ability to show up for others may be overlooked forms of wealth
- How to pursue outdoor freedom without romanticizing irresponsibility, poverty, or precarity
Links, Mentions, and Related Content
- Issues: On Wilderness and Flourishing
- Essays: How Much Does Backpacking Really Cost?

Discussion
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Companion forum thread to: Episode 146 | Dirtbag Rich with Blake Boles
Ryan Jordan interviews Blake Boles, author of Dirtbag Rich, about redefining wealth through time, purpose, flexibility, and outdoor freedom. They explore dirtbag culture, careers, housing, relationships, risk, and the pursuit of a life built around adventure, simplicity, and meaningful time outside before retirement.
Hi Ryan, your voice is muted on the podcast
Hi David,
This has been fixed with the podcast file on the Website. It should be updated with Apple Podcasts, Spotify, and the other podcast apps shortly, but this can take up to 72 hours.
Cheers,
Chase
He who spends the most days outdoors wins.
If you’re a trust fund baby who doesn’t have to work, no worries, you can have it all. But for the vast majority of true dirtbag hikers everything’s a tradeoff.
Marriage and children are going to be virtually impossible because of the time, money and stability needed to maintain a solid family. If you’re a male, romance and intimacy are something you’ll probably have to mostly forgo unless you’re a 1 out of 1,000 stunning Giga-Chad. In our society women generally don’t go for broke dirtbaggers who haven’t showered for days. It’s easier for women to find love in the backcountry and please don’t try to give me a PC narrative on why that’s not true.
Dirtbag hikers work just enough to save enough money for the next thru-hike, typically 3 to 6 months, and preferably at a job where the employer matches their 6.2% social security input. Main thing is to have 40 quarters of SS paid in at 65 to get Medicare and at least some SS income later on. The bar is pretty low on getting that done. You’ll need to be on Medicaid before age 65 and income must be kept low enough to qualify….THAT”S HUGE! And stay away from non Medicaid expansion states which are mostly in the Southeast US.
Blake is so right, the rent monster is what enslaves people more than anything, so when it comes time to work again a dirtbag hiker has to find low rent and that can usually be done in most parts of the US. Just go on craigslist and run an ad for “Rooms Wanted” or look for ads saying “rentals to share”. But NEVER sign a lease for an apartment because that will take up 40% plus of your income and you’re committed. When not working there are millions of acres of BLM and National Forest lands in the west where you can camp for up to 2 weeks until you need to move again. Get a 27 dollar a month Planet Fitness black card membership so you can take showers….they are located everywhere.
Food should be number 1 expense. Practice minimalism on all levels. It might be necessary to rent a 5′ X 5′ storage unit to place your worldly possessions (maybe 50 to 70 dollars per month).
Americans are brainwashed into the materialist consumer culture that keeps them on the plantation, a veritable treadmill that makes them working stiffs, slaves if you will. And why are Americans so overweight and unhealthy? I say it’s because they simply don’t walk enough. What did humans do for more than 100,000 years before civilization when they were hunter-gatherers? They walked for about 8 to 12 hours a day. Now when I drive by a fast food restaurant I see cars lined up 10 to 20 deep with motors running and fat a** Americans who are too lazy to park the car and walk inside where there might only be 1 or 2 people in line.
That buddy you may depend on for shelter is now married and has two kids. When you’re gone for a long time, life goes on without you. When you return your head is in a different place from what’s considered normal in structured society. Your values change. It becomes hard to accept the posturing that accompanies emerging yourself totally into a world created by others. You see past the structure, back into the woods where you left reality behind until your next visit.
Actually, I thought it was glossed over quite a bit.
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