About

Dolomites 2024 by Nate Singer

[scroll down for a traditional bio]

About the temporary agglomeration of atoms known as Blake

I design adventures—for myself, for my friends, and for young people.

But designing is less than half the fun. You’ve got to take the adventure, too.

Computers were an early love, but I never wanted a desk job. Too much sitting, too many rules, too little fresh air.

I flirted with becoming a high school science teacher, but I never understood why most teachers just teach. What about the doing? Normal teaching positions (public or private) leave little time for doing the thing you propose to impart to students. Where’s the passion? Where’s the skin in the game? Young people can smell that stuff. They know when you’re just showing up, clocking in, and going through the motions. I wanted to become a different kind of teacher. So I quit my astrophysics major, designed my own course of study in alternative education theory, graduated from UC Berkeley with a degree no one ever heard of, and launched into the world without much of a plan.

I threw myself into adventure: travel adventures, wilderness adventures, entrepreneurial adventures, and creative adventures. Some alone, some with friends. These adventures brought me to new worlds and hidden communities, where I discovered yet more inspiration, motivation, and co-conspirators. The flywheel started spinning, and it never stopped.

At age 25 I started Unschool Adventures, a tiny travel company that let me earn money by exploring the world, sharing my passions and curiosities, and giving teenagers real-life freedoms and responsibilities. I hired my friends from the world of outdoor and alternative education. I almost never repeated a trip. And I only ran a few trips each year, ensuring that I’d have plenty of time left over to continue doing the thing I taught.

Around the same time, I wrote my first book, connecting the ideas of unschooling (full-time self-directed learning), adventure, and the “real world” (as symbolized by college admissions). A small Canadian publisher purchased the manuscript, and suddenly I was a published author. I started blogging, speaking for homeschool conferences and alternative schools, and making friends across the realm of self-directed education. Three more books on similar topics followed.

No one goes into education or writing for the money. Between the travel programs and book royalties, I earned enough to pay my way and save a bit each year—but only if I lived like a dirtbag.

“Dirtbag” is a term adopted by rock climbers, long-distance hikers, and others whose deep love for the outdoors leads them to take creative and extreme actions to minimize their cost of living and maximize their free time. Maybe you’ve met a dirtbag climber living out of their van or truck, given a ride to a scruffy thru-hiker along the Pacific Crest Trail or Appalachian Trail, or met someone who’s traveled around the world or lived on their bicycle for years on end. These are all dirtbags, and once I got to know a few, I realized that we’re cut from the same cloth. I’m not a hardcore climber, badass thru-hiker, or hobo hippy—but I am willing to live differently in order to avoid full-time servitude.

In my early 30s, after briefly considering the house/wife/kids trajectory, I resolved instead to double down on adventure: to have no fixed address, to migrate between the people and places I love most, and to continue reading, writing, exploring, nurturing relationships, moving my body, and working with young people in unique ways. I spent little on rent, never owned furniture, learned to cook inexpensive meals with universal ingredients, said “no” to many forms of entertainment, and said “yes” to shared housing, frequent transitions, and a minimal safety net. In 2020, I started writing about this way of living: a project that evolved into my next book, Dirtbag Rich.

In recent years I’ve dedicated my dirtbag riches to:

  • Fusion dance: a form of partner dance I mostly do in Europe, adorned with Argentine tango, contact improv, urban kizomba, contemporary, clowning, and whatever other dances I’ve encountered over the years.
  • Bicycle touring: very long bike rides, with or without camping gear, to visit old friends, make new friends, and experience the world at 10 miles per hour.
  • Epic hikes and runs: around Lake Tahoe and the Bay Area, to the Tahoe Crest, across New Zealand, and through the High Sierra.
  • Writing more vulnerably and provocatively: about my doubts regarding adventure, how I’ve made money, my conflicted thoughts about having kids, what matters in a romantic partner, worries for the far future, loving a mountain range, the beauty of trail running, and redistributing your privilege.

Now you know something about me!

2025 📸: Maria Kravchik

Traditional / third-person / educator bio

Blake Boles is the founder and director of Unschool Adventures and the author of Why Are You Still Sending Your Kids to School?, The Art of Self-Directed LearningBetter Than College, and College Without High School. He has delivered over 80 presentations for education conferences, alternative schools, and parent groups. Blake and his work have appeared on The New York Times, The Christian Science Monitor, BBC Travel, Psychology Today, Fox Business, TEDx, The Huffington Post, USA Today, NPR affiliate radio, and the blogs of Wired and The Wall Street Journal. From 2015-2022 he hosted the Off-Trail Learning podcast.

In 2003 Blake was studying astrophysics at UC Berkeley when he stumbled upon the works of John Taylor Gatto, Grace Llewellyn, and other alternative education pioneers. Deeply inspired by the philosophy of unschooling, Blake custom-designed his final two years of college to focus exclusively on education theory. After graduating he joined the Not Back to School Camp community and began writing and speaking widely on the subject of self-directed learning.

In his previous lives, Blake worked as a high-volume cook, delivery truck driver, summer camp director, Aurora Borealis research assistant, math tutor, outdoor science teacher, camp medic, ski resort market researcher, web designer, and windsurfing instructor. His biggest passion is sharing his enthusiasm and experience with young adults who are blazing their own trails through life. He was born in 1982.

For more backstory, see this 2019 interview, this 2016 profile, and the longer story (2017).

Speaking for a parent group in Sacramento, 2019.