How To Be Dirtbag Rich (Guest Post by Blake Boles)
Time, money, and purpose on the pathless path
March 29th, 2026: Greetings from Taiwan. Today’s post is from an internet friend, Blake Boles, who has been hacking a living doing his things a bit longer than me.
He’s got a new book coming out, titled Dirtbag Rich, in which I play a very minor role, based on a convo we had on his podcast last year.
He pitched me on writing an essay for the newsletter and said, send me what ya got. I liked it. Especially this frame:
Where are the people who have found ample time, money, and purpose in their 20s, 30s, and 40s? What about those with children? What about those who don’t particularly love dirt? What about those with difficult upbringings, or constant anxiety, or, or, or… The stories are all there.
I also just love the title Dirtbag Rich pairing. It might be better than Pathless Path. The combo of “dirtbag,” a term often embraced by climbers who build their lives around bare minimum living, with rich, is nice.
Without further ado…
Time, money, and purpose
If you’re a Paul Millerd fan, I suspect you already think differently about time, money, and purpose.
Time: You try hard to remain in control of the hours of your day, week, and year. Perhaps you work regularly but part-time, intensely but seasonally, or possess an otherwise normal job that allows significant breaks. The time of your life does not belong to your employer, your clients, or anyone else—it is yours alone.
Money: You attempt to earn a substantial amount relative to your efforts, perhaps via a high hourly wage, big payouts after big gigs, or some version of (so-called) passive income. Paired with low expenses, you can subsist happily on a lower income—sometimes even “poverty wages”—and enjoy the spacious freedom necessary to do what you love.
Purpose: You really, truly attempt to “do what you love,” right here, right now, in your one life on Earth. Instead of making purpose wait for the weekend, you actively seek it, compensated or not, day in and day out. Because why else would you so carefully manage your time and money? What would be the point?
While the status quo tells you to earn money at the expense of time and purpose—two resources you’re supposedly meant to reclaim in retirement (a.k.a. the pre-death siesta)—you have resolved to take a different approach.
Some call this the pathless path, a label I quite enjoy.
For me, another term fits even better: dirtbag rich.
What’s a dirtbag?
The first dirtbags were hardcore rock climbers in Yosemite Valley who camped illegally, showered infrequently, and scavenged for meals. When they needed money, they’d leave the Valley to paint houses, wait tables, teach skiing, or even take a desk job: anything to refill their coffers and get back to the big walls. They lived like bums in pursuit of the good life.
Today dirtbags come in many flavors, not just “climber” and “white male.” Some are trail runners, mountain bikers, long-distance hikers, backcountry skiers, cross-country cyclists, or endless-summer surfers. Others are dancers, slackliners, or perpetual travelers. All are passionate. All are extreme. None are what the mainstream would describe as “balanced.”
Some dirtbags live in vans, trucks, or tents. Others couchsurf, hitchhike, or stay with friends. Some do pay rent: just not very much, and not for very long. For dirtbags, full-time, full-price rental contracts lie somewhere between a luxury and an obscenity.
Many dirtbags come from middle-class security. Some come from upper-class privilege. Others come from next to nothing.
All dirtbags revere nature, movement, and thrift. All struggle to fit into conventional society. All want to be left alone to do what they love, while they also yearn for membership in a tight-knit community of the similarly obsessed.
Many who lead such lives aren’t aware of the label “dirtbag.” Of those who are aware, many don’t welcome its associations. I understand their aversion, but I like the term.
To me, being a dirtbag simply means that you’re too busy following your bliss to worry about a little dirt under your nails. It means you’re doing something right.
Freedom = moving your body swiftly through nature
As I recount in my new book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, I never made a very good dirtbag.
My attempt to hike the Pacific Crest Trail at age 22 ended two weeks after it started, catapulting me into a multi-year crisis of commitment. I failed to live happily outdoors like a “real” dirtbag, yet I was also incapable of holding a “real” job like a normal member of society.
Three months of soul-seeking in South America revealed the first glimpses of an answer: I needed to take the middle path. I needed to craft a new way of living in the liminal space between hardcore dirtbagging and conventional wealth-seeking.
Because the truth was: I loved sleeping in the dirt, in a bag. I loved it when I was 22, and today at 43, I still do. Living like a hobo in the mountains is one of my “peak experiences,” and that’s not going to change.
Anytime I move my body swiftly through nature, in fact—whether backpacking, day hiking, trail running, bicycle touring, or swimming in alpine lakes—everything tastes, smells, sounds, and feels more intense. The same goes for international travel. Whenever I’m in motion, I remember more details, and everything feels more “real.” Daily life in cities, in contrast, is too easily forgettable and “unreal” (with the exception of social partner dancing: the one thing that keeps me circling back to big cities).
If you’re anything like me, then you, too, face a series of dilemmas:
You derive profound purpose from moving your body through nature, yet you’re not ready to live like a total dirtbag.
You won’t be a mere weekend warrior, nor will you drop out of polite society.
You crave wilderness immersion, long-term travel, retreats with friends, and other transformative experiences, while also desiring to put something away for the future.
You are an irrational, implacable, exuberant creature who wants it all—time, money, and purpose—with very few compromises. Heaven help you.
Impossible contradictions are fun
As I navigated these tensions throughout my twenties and early thirties, many questions remained. How could I earn enough while only working part-time? How would I manage without a home base? What if I wanted a family? And beneath them all: What if I was making a giant, life-shattering mistake by not swallowing my discomfort, burying these impossible desires, and getting on with a normal existence?
I knew that every path has trade-offs. If I lived for adventure, I might not have kids. If I had kids, I’d certainly take fewer adventures. Travel would change me, just as rootedness would change me. Working for myself might be the best thing I ever do, and turning my passion into a business might suffocate it.
No one can have it all. But maybe, just maybe, I could have more than the world promised.
And—spoiler alert!—I have.
I ended up creating a little travel company for unschooled teenagers: one that let me share my love of travel and nature with delightful young people while also earning decently in a brief period. I dedicated my newfound free time to nature, dance, travel, adventure, and writing books about self-directed learning. I did not start a family, but I did develop deep friendships across the world and find profound meaning in playing a unique role in the lives of other people’s children.
Attempting to live dirtbag rich means navigating a series of seemingly impossible contradictions. Some of these contradictions are very real—like balancing freedom and romantic attachment—while others are but smoke and mirrors. As with any serious attempt to live differently, fear of the unknown stops most from ever trying. Nor is it a mere privilege issue, as wealthy people are often the most chained to convention; the ideal setup may be moderate privilege + high idealism.
Yes, it’s possible. Yes, it’s hard. On any pathless path, it’s a question of what kind of glory you crave and what kind of difficulties you can face down.
How (and where) to begin
Ask yourself that age-old question: “If I suddenly had [ridiculous sum of money] in the bank, how would I live differently?”
If the answer is “not much differently”—if you’d reduce your working hours a bit, for example, but not change your work—then you’ve already struck a magical balance of time, money, and purpose. Keep it up!
If the answer is “VERY, VERY DIFFERENTLY”—if you’d pursue a whole new vocation or wander in the woods indefinitely—this indicates a need for change, and a possible new direction for your life.
There’s no silver bullet for this kind of stuff; distrust anyone who insists otherwise. Rather, you need a wealth of examples.
This is what Paul has achieved with his books and the Pathless Path Community, and it’s what I’m attempting with my dirtbag rich interview series (which includes Paul). Where are the people who have found ample time, money, and purpose in their 20s, 30s, and 40s? What about those with children? What about those who don’t particularly love dirt? What about those with difficult upbringings, or constant anxiety, or, or, or… The stories are all there.
To begin living differently, you need a bunch of role models. None will exactly match your background, values, risk tolerance, or other constraints. Each will have something to teach you. Listen to their stories: the long version, not the soundbyte. When one resonates, reach out and ask a few follow-up questions, as a 22-year-old adventurer from Chicago did with me yesterday. (Remember the promise of the early internet: You can just find interesting people and connect directly with them!)
This is how any pathless path—or dirtbag rich life—begins and evolves. Watching, thinking, feeling, researching. Getting honest, getting vulnerable, getting in touch. And at some point: making a big move. What that specific move is, I cannot say. All I know for sure is that at some point, you must stop gathering data—and act.
As for me, I’m going to keep dancing, cycle touring, working with unschooled teenagers, and losing myself in the wild places of the world. I’ll keep visiting friends and family, showing up for other people’s kids, writing for a small but engaged audience, and remaining open to the possibility of another big pivot.
This is a life I wouldn’t dream of trading away for a pile of money, the myth of retirement, or some other distraction. It’s far from perfect, it’s still fraught with uncertainty, and it could all end tomorrow. But we’re not here to win the game of life—we’re here to play progressively more interesting levels. Onwards.𖤓
It’s Paul Again. If you want to check out his book, it’s $4.99 on Kindle or on his website. I already grabbed one.
 | A guest post by
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I’m a self-described "dirtbag" who lives on a sailboat full-time with his husband & cat. We’ve lived this way for the past 10 months after exiting our upper-middle-class lives. We’ve sailed 4,000 miles in 3 countries with very few possessions or bells & whistles. Other sailors are super fancy, but we’re not. We don’t even have a working fridge. We still have constraints. But this is our version of rich, because we’ve chosen our constraints. This is our version of enough.
There are so many ways to be rich in this world – even on low wages & relatively small savings. We don’t need to give up all our money, time, & purpose for other people, "later," "maybe," "someday." How do I know? Because when we first considered this lifestyle, I thought it was impossible for people like us. That we couldn’t afford it. That there’s no way it could be possible, otherwise "wouldn't everyone do it?" Yes, it took a few years to save enough financial runway, a year to get that capable boat, & many months to become proficient sailors. But we now have a life that many people put off for decades. And the reality is way more people can do it than the number who initially think they can.
We still need to live "within society" though, to have *meaningful* work, to make *enough* money, to *contribute* in ways that are important. But for now, we're aiming to stay "dirtbag rich" on our terms (not anyone else's). And it looks like it WILL work.
As Blake (& Paul) talk about, many of us can do it now – or at least ASAP. Some of us just need to rebalance time, money, & purpose – even for a shortish amount of time. We also need better role models. And we need to apply our amazing work ethic toward our own version of success.