#108. One Man's Choice of an Unconventional Life

Blake Boles describes here his life of high freedom, low income, and deep purpose.

Dear friends,

I’m always interested in people who choose, very deliberately, to live quite differently from the societal norm. They epitomize, in a way, the theme of this Substack—Play Makes Us Human. They have chosen to maximizes their control over their own life, their own way of finding enjoyment and meaning. Each such story is unique, not something to be mimicked, but something that can inspire one’s own thinking about how one wants to live. I was delighted, therefore, to read a prepublication draft of Blake Boles’s new book, Dirtbag Rich, about the life he has chosen. After reading it, I invited him to write a précis of it for Play Makes Us Human, and here it is. If what you read here intrigues you, you should read the book. Here are some places where you can purchase it.

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Blake’s Story

Hi, I’m Blake.

I’m not wealthy or famous.

I don’t have a house, car, spouse, child, advanced degree, or prestigious title.

I lack many things that others my age possess.

What I do have is my own little version of the good life: one overflowing with freedom, nature, travel, adventure, romance, and friendship.

For almost two decades now I’ve worked just a few months each year. The rest of the time I spend reading, writing, hiking, biking, dancing, thinking, traveling, dreaming, and conversing.

I’m not subsidized by my family or the government. Nor did I sell a company, ride the stock market, go viral, traffic human organs, or take an online course revealing the one secret that will make all your financial dreams come true.

Rather, I found a form of work that I genuinely enjoy. Work that does good, pays well, and doesn’t monopolize my life.

“Found” isn’t really the right word. I stumbled, tinkered, and charmed my way into this work. Year after year, I do it all again. Nothing is guaranteed, but this fact energizes me.

I don’t have a permanent residence. At various points, all of my possessions have fit into a small storage unit, the back of a car, or a few plastic bins. When I tire of migrating, I settle down for a few months or longer. Then I pick up and move on, in pursuit of the people, nature, and activities I cherish most. No one place holds my heart. I am geographically polyamorous.

Relationships are my first safety net. Good health is my second. Savings are my third.

I may not earn much, but compared to how I spend, it’s a ton.

I’m not conventionally rich. I’m dirtbag rich.

Blake with teen unschoolers at Not Back to School Camp (2010)

To earn money, I take teenagers on international trips through my little travel company, give occasional talks for alternative schools and homeschool conferences, and publish books about self-directed learning.

Work is important to me. I never wanted to become a parasite or grifter. But a brutal, multi-year, quarter-life crisis showed me that normal employment simply wouldn’t suit me. Coming of age amidst the 2008 financial crisis, while my peers were happy to take any job, I found myself running hard in the other direction. Two decades later, I’m still running—but I’m running on a beautiful singletrack dirt trail, rather than a standard treadmill of wealth and status accumulation.

For me, becoming “dirtbag rich” is about finding a magical balance of time, money, and purpose:

• Time: I’m dedicated to remaining in control of my day, week, and year—which might look like working regularly but part-time, working intensely but seasonally, or having an otherwise normal job that allows significant breaks. The point is to remain flexible, autonomous, and far, far away from even the slightest whiff of eternal servitude.

• Money: I aim to earn a substantial amount relative to my efforts—whether through a high hourly wage, big payouts after big gigs, or some version of so-called passive income—in order to stay flexible. But this only works if I also keep my expenses low. By deliberately subsisting on a lower income, I can enjoy the spacious free time necessary to follow my passions. It feels paradoxical, but I’m “high pay” and “low income” at the same time.

• Purpose: Finally, I seek profound meaning in both my paid work and free time activities. I don’t make purpose wait for the weekend or retirement. I do what moves me, compensated or not, day in and day out. What better reason is there to carefully manage your time and money?

In a typical year I’ll run one or two programs, adding up to 4-8 weeks of intense, joyful face time with young people (plus a little laptop prep). I’ll spend two weeks working at Not Back to School Camp, give a few parent talks and teen workshops, and… that’s it! Averaged over the year, it’s something like 15 hours a week of dedicated “work.” (Here’s a full breakdown of how I’ve earned money, and how much.)

What do I do with the remaining hours of the day and weeks of the year?

• I go partner dancing, take long hiking adventures and bicycle tours, and go trail running.

• I read voraciously, write constantly, and learn more about history, economics, education, politics, psychology, sociology, and spirituality. (Sometimes this leads me to write books that earn money. Mostly it does not.)

• I visit family and friends, nurture new connections through dance and Couchsurfing, and generally assume the role of “the one who stays in touch.”

• I travel—no longer in search of novelty, but to revisit the places to which I’m deeply attached: the mountainous western USA, Argentina, New Zealand, and Western Europe. (It’s usually more about the people than the place.)

Hiking on Tahoe Rim Trail, 2021

Not everything is rosy. Relationships are challenging without a fixed address. I love working with other people’s kids but have deeply conflicted thoughts about raising my own. My body isn’t fully reliable. And envisioning the far future isn’t as simple as “retire comfortably in the house I own outright.”

This is one big reason I wrote Dirtbag Rich: to explain the conflicting pressures, anxieties, and trade-offs inherent in living this way. I also wanted to document the lives of the other “dirtbag rich”—including those with children, those who don’t particularly love dirt, and those with challenging upbringings—who have found magical balances of time, money, and purpose, without relying upon family money or neglecting the practical challenges of paying for housing, healthcare, childcare, or retirement. (In case you’re wondering: “dirtbag” is a term of endearment in the outdoor community for those who pursue their bliss, live on a shoestring, and reject the rat race.)

But a bigger reason is this: there are so many different ways to become an adult, and young people need role models. In my early twenties, I found few honest brokers to emulate. I desperately sought the voices of those living genuinely “alternative” lives, those willing to talk openly and honestly about escaping the conventional narrative. Now that I’ve accomplished this in my own, weird, idiosyncratic way, I’m ready to contribute.

Books aren’t as flashy or viral as a polished YouTube, TikTok, or Instagram account, but they still earn respect in our culture. And if you’re a young person trying to convince your friends or family that you can live far outside the norm—in the name of joy, authenticity, and your mental and physical health—handing them a book is the best way to go.

In Europe with first copy, 2025

In the end, it doesn’t really matter if you live “inside the box” or “outside the box.” What matters is the depth & quality of your relationships, how much good you do in the world, whether you can regularly pursue your bliss, and if you were hit by a bus today, you might die happily.

No matter which path you’re walking—happy trails.𖤓

Blake.

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Final Thought

Thank you, Blake. It takes courage to live a life outside the norm. But then, living well—whether inside or outside the norm or on the edge—always takes courage.

And now, readers, I’m interested in your reactions. Are the basic principles of how Blake describes his life—in terms of work, time, money, and purpose—relevant to how you would describe your life, however different your life might be from his? To me, the biggest general moral of Blakes story has to do with going about life consciously, in charge, making decisions about how we want to live and then courageously doing it.

Again, for alternative ways of buying Dirtbag Rich, go here.

With respect and best wishes,

Peter