Episode Details

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