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

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