How to Live an Unconventional Life of Adventure and Purpose by Becoming “Dirtbag Rich” with Blake Boles
What would it mean to stop measuring your life by the conventional yardstick and start building one that actually fits?
Blake Boles is a writer, experiential educator, and the founder of Unschool Adventures, a travel company for self-directed teenagers, which he has run since 2008. He is the author of several books on alternative education and self-directed learning, and his newest book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, was released in March 2026.
In this episode, Blake and I get into the philosophy behind "dirtbag rich" living, including what it really means to pursue a high-freedom, low-income lifestyle while still navigating the demands of modern capitalism. We also dig into the practical side of how to make a non-traditional financial model actually work, and talk about purpose, downward mobility, unschooling, outdoor adventure, and so much more.
If you've ever wondered whether there's a middle path between grinding toward a distant retirement and going full dirtbag with no financial safety net, this conversation is going to give you a lot to think about. Blake shares a lot of real practical substance in this one, alongside some genuinely fresh thinking about how to measure wealth, what freedom actually requires, and what gets in the way of most people finding their version of a dirtbag-rich unconventional life.
What does "enough" look like for you, whether that's money, time, adventure, or something else? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Tune In To Learn:
Why the original dirtbag culture offers a useful framework, even if you'll never live in Yosemite full-time
How Blake figured out a way to earn good money in short bursts and stay free the rest of the year
Why "how do you know when you're wealthy?" is a more useful question than you might expect
What the FIRE movement often gets wrong about making a clean break from work
How to think about "downward mobility" as a feature rather than a failure
Why having freedom from something isn't enough without also knowing what you're free to do
What the real risks of a dirtbag rich lifestyle actually are, and how to go in with clear eyes
How purpose shows up differently for different people, and why measuring it in "I get to" days works
Advice for attracting the ideal clients and building work that doesn't eat your life
Why getting your ideal client to feel genuinely excited to work with you is the job before the job
And so much more
Resources:
Sign up for our FREE newsletter
Blake’s website
Dirtbag Rich book
Unschool Adventures
Want More?
The Vagabond's Way: Meditations on Wanderlust, Discovery, and the Art of Travel w/ Rolf Potts
The 5 Best Hacks of “All the Hacks”: Travel, Money & Life Optimization with Chris Hutchins
Digital Detox: Downsizing Your Digital Life to Create Freedom + Reboot Your Lifestyle Business with Corbett Barr
Thanks To Our Sponsors
Become a Fora Advisor today at foratravel.com/zerototravel
Check out Morning Brew Daily for business news that's actually fun.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Blake Boles is a writer, experiential educator, and the founder of Unschool Adventures, a travel company for self-directed teenagers, which he has run since 2008. He is the author of several books on alternative education and self-directed learning, and his newest book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, was released in March 2026.
In this episode, Blake and I get into the philosophy behind "dirtbag rich" living, including what it really means to pursue a high-freedom, low-income lifestyle while still navigating the demands of modern capitalism. We also dig into the practical side of how to make a non-traditional financial model actually work, and talk about purpose, downward mobility, unschooling, outdoor adventure, and so much more.
If you've ever wondered whether there's a middle path between grinding toward a distant retirement and going full dirtbag with no financial safety net, this conversation is going to give you a lot to think about. Blake shares a lot of real practical substance in this one, alongside some genuinely fresh thinking about how to measure wealth, what freedom actually requires, and what gets in the way of most people finding their version of a dirtbag-rich unconventional life.
What does "enough" look like for you, whether that's money, time, adventure, or something else? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Tune In To Learn:
Why the original dirtbag culture offers a useful framework, even if you'll never live in Yosemite full-time
How Blake figured out a way to earn good money in short bursts and stay free the rest of the year
Why "how do you know when you're wealthy?" is a more useful question than you might expect
What the FIRE movement often gets wrong about making a clean break from work
How to think about "downward mobility" as a feature rather than a failure
Why having freedom from something isn't enough without also knowing what you're free to do
What the real risks of a dirtbag rich lifestyle actually are, and how to go in with clear eyes
How purpose shows up differently for different people, and why measuring it in "I get to" days works
Advice for attracting the ideal clients and building work that doesn't eat your life
Why getting your ideal client to feel genuinely excited to work with you is the job before the job
And so much more
Resources:
Sign up for our FREE newsletter
Blake’s website
Dirtbag Rich book
Unschool Adventures
Want More?
The Vagabond's Way: Meditations on Wanderlust, Discovery, and the Art of Travel w/ Rolf Potts
The 5 Best Hacks of “All the Hacks”: Travel, Money & Life Optimization with Chris Hutchins
Digital Detox: Downsizing Your Digital Life to Create Freedom + Reboot Your Lifestyle Business with Corbett Barr
Thanks To Our Sponsors
Become a Fora Advisor today at foratravel.com/zerototravel
Check out Morning Brew Daily for business news that's actually fun.
Learn more about your ad choices. Visit megaphone.fm/adchoices