41. Flipping the Script on Wealth: Living Dirtbag Rich with Blake Boles
The ethos, economics, and bloodsport of choosing time, nature, and purpose over money
I asked Blake to “Make it sting to the corporate stiffs of us out there.” It was a flourish on my root question, which was an invitation to animate a week in the life of the Dirtbag Rich. Suffering a recent bout of freedom deficit syndrome myself, I was in need of a good swift kick in the soul pants.
Instead of rubbing his freedom salt in my 40-plus-hours-a-week-job wound, Blake offered me The Wednesday Test.
He served it up with this devilishly simple question.
“If it’s a particularly nice Wednesday, and you want to be out doing what you love in the outdoors in the middle of the day, can you do that? Can you make that happen?”
How’s that for a fucking litmus? For me, it was a nesting doll of contemplation. I thought, No, I don’t have that right now, but I’ve had it before. I mean, I could pull it off here and there, but not as much as I’d like. What would need to change in my life so I could have it again? And what are the tradeoffs?
Blake’s new book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, is full of the types of questions that can help us avoid sleepwalking through life.
I had Blake on Nature Junkie Radio recently and we delved into all of it. Beyond the juicy, life check-in provocations, I have mad respect for the fresh angle Blake took on the topic of dirtbagging it.
He ran the opposite direction of the Instagram trap. Instead of over-romanticizing it with idyllic photos and stories that reek of bullshit, he laid out the ethos along with a warts-and-all view of the tradeoffs that come with choosing free time and purpose over money and security. What emerges is a blueprint for an against-the-grain lifestyle that he describes as “Bloodsport.”
The thing that blew my mind was the seriousness with which he, or anyone successfully pulling off this way of living, approaches the economics of the enterprise. It’s no joke if you’re playing at the pro level, which Blake has for decades.
But it’s not all swim upstream grit.
There is a beautiful relief woven throughout this way of living. Part of it is the depth of connection with friends around the globe, and family, that the freedom affords. The other part is tilting the scales of life away from the rat race and toward nature.
Blake’s take on the role of nature in the life of the Dirtbag Rich was crystal clear. And it feels poignant in these often disconnected, expensive, and hollowed-out times.
“I think you need to have meaningful experiences that cost no money, or very little money. And that’s what being out in nature fundamentally promises people.”
I came away from this book and conversation realizing that one of Blake’s most powerful questions, “How are you spending the time of your life?”, is useful at any stage of life.
It’s been a nudge for me and my wife to plan better for whatever the hell retirement looks like. For my boys (both in the early adulting phase), I hope it will help them see that life has many potential pathways and that they’re free to carve their own. My dad even bought a copy too.
As always, episode notes and photos from Blake’s dirtbag life below.
Enjoy the ride,
Jeff
A Few Snaps of Blake Living Dirtbag Rich
Episode Summary
In this episode I sit down with writer, educator, and author Blake Boles to explore an unconventional question. What if wealth had less to do with money, and more to do with freedom, purpose, and plenty of stoke-filled play time in nature?
Drawing from his book Dirtbag Rich: High Freedom, Low Income, Deep Purpose, Blake shares the ethos and practical realities behind designing a life centered around nature, flexibility, doing meaningful work, and knowing what it means to have “enough.” We dive into the often hidden economic enterprise of alternative lifestyles, the social pressures that keep people trapped in the rat race, the tradeoffs required to prioritize freedom, and the role nature plays in the lives of the Dirtbag Rich.
We traverse a bunch of fun topics from trail running, backpacking in the Sierras, van-life mythology, retirement culture, community living, stoke, purpose, and the emotional tension between security and aliveness. Rather than romanticizing the dirtbag lifestyle, Blake offers a sober, nuanced, and deeply human examination of what it actually takes to build a life around freedom and connection.
This episode is for anyone who has ever taken a pause from the grind and quietly pondered Blake’s juicy, and often catalytic, question: How am I spending the time of my life?
Episode Links
Dirtbag Rich: High Freedom, Low Income, Deep Purpose
Blake’s Instagram @blaketotheboles
Unschool Adventures Instagram @unschooladventures
Blake’s Podcast - Dirtbag Rich
Blake’s Substack The Adventures of Blake
Brendan Leonard’s Instagram @semi_rad