Blake Boles: writer, traveler, dancer, teen wrangler

May 26, 2025

In this engaging conversation, Blake Boles, a writer and traveler known for leading self-directed adventures for teens, shares his journey and philosophy on freedom, purpose, and security. He discusses his love for minimalism and owning less, while emphasizing the importance of human connections formed through dance and travel. Blake critiques conventional lifestyle literature and reflects on his own influences from alternative communities. The duo also explores the transformative power of unschooling and wilderness experiences, highlighting the challenges and joys of a non-traditional path.

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INSIGHT

Freedom as No Servitude

Blake defines freedom as "not being available for servitude," focusing on work, education, and relationships.
He values friendship as embodying perfect equality and full consent, key to his sense of freedom.

ANECDOTE

Living Out Of Carry-on Bags

Blake lives out of three or four carry-on-sized bags plus his touring bike while traveling in Europe.
He rents furniture and embraces not owning a permanent home or lots of possessions.

ADVICE

Google Calendar for Stability

Use tools like Google Calendar to maintain stability amidst a mobile lifestyle.
Extensive planning provides a sense of order and reduces stress while on the road.

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Blake Boles is a 42-year-old writer, cycle tourist, trail runner, partner dancer, and California-born temporary European expat who leads international trips for self-directed teenagers and young adults. (blakeboles.com)

In this special episode, former guest Jenny Abegg interviews Blake about what he's doing with his life, the Dirtbag Rich project, his early influences, and how he thinks about freedom, purpose, security, and more. Topics include:

Freedom as “not being available for servitude”
His view of long-term security and alternative retirement plan
What the hard moments look like in a life on the road
His undying love for the Deutschland Ticket (an unlimited travel pass covering all forms of public transport in Germany)
How much stuff he actually owns (and the rules he sets for himself around possessions)
Finding stability through extensive planning (and Google Calendar), and security through extensive friendships (his friend buckets include: dance, outdoors, college, and two summer camp communities)
Why getting older is mostly awesome
Who Dirtbag Rich is actually written for (and why it’s not 40/50/60-year-olds)
His allergy to most "lifestyle" books (see: The 4-Hour Workweek) and how he's trying to do better
The mysterious overlaps between unschooling, tiny houses, partner dance, love of wilderness, and the pursuit of dirtbag riches
His biggest early influences: the Berkeley Student Cooperatives, Deer Crossing Camp, and Not Back to School Camp—yin and yang
The magic of working your ass off, surrounded by people you deeply respect, in a beautiful natural environment
How pointless school experiences led him to a deeper search for purpose, which he found in off-trail backpacking, reading alternative education theory, and independent foreign travel
The flywheel of total aliveness, curiosity, enthusiasm, and positivity—and how keeping the flywheel going became his purpose
What idolizing a dirtbag hiker (and failing to hike the Pacific Crest Trail) taught him at age 22
His money situation
How his life is currently not working

And finally, if you stick around to the very end: Jenny & Blake’s illicit scheme to create a "dark night of the dirtbag soul" OnlyFans.

Full transcript: dirtbagrich.com/blake