If you enjoyed Off-Trail Learning, check out my new podcast, Dirtbag Rich, where I dive deep with working adults who have managed to strike that elusive balance of time, money, and purpose—without giving up on their wildest dreams. Find Dirtbag Rich wherever you subscribe to podcasts, or visit dirtbagrich.com ..read more

Guest host Zen Zenith returns to interview Blake about his obsession with adventure. What exactly makes an adventure? How is adventure connected to self-directed learning? Is adventure just for privileged people? Why can’t Blake just settle down and lead a normal life? How do Unschool Adventures trips create a sense of adventure for both teens and trip leaders? Does adventure become harder as one grows older? Does Blake even have a retirement plan?! And what comes next? Read Blake’s “Notes on Adventure” here: https://blakeboles.substack.com Zen Zenith is a grown unschooler, musician, guitar te ..read more

Chris Balme (chrisbalme.com) is the founding head of school of The Millennium School and the author of Finding the Magic in Middle School. After briefly flirting with public school teaching, Chris ran an apprenticeship program for middle schoolers for a decade before creating The Millennium School in San Francisco, where he served for seven years. We discuss Chris’ early infatuation with democratic free schools, how the Millennium School takes the developmental needs of middle schoolers seriously, the life-changing power of peer advisory groups, learning through quests, authentic audiences, an ..read more

Liam Nilsen (https://liam.media) is a designer and educator based in Åårhus, Denmark. He’s a former member of the LEGO Idea Studio, the founder of an Agile Learning Center, and a life-long unschooler who didn’t start reading until age 9 — at which point he fell in love with the written word. Liam and I discuss our lives as readers, including the books that have changed our lives, how we discover new things to read, books vs. articles vs. newspapers vs. social media, old favorites that now embarrass us, writing inside books, and keeping books vs. giving them away. We also discuss the virtues of ..read more

Grace Llewellyn is the author of The Teenage Liberation Handbook, the founder of Not Back to School Camp, a one-time middle school English teacher, and a luminary in the unschooling movement. In this episode we discuss the third (and final) edition of The Teenage Liberation Handbook, released in late 2021. Grace talks about writing the original book in 1991, how it became an underground classic, how her views on education (and her relationship to her 26-year-old voice) evolved over three decades, and how the book was updated for the 21st century. I had the pleasure and honor of serving as Grac ..read more

Takeru “TK” Nagayoshi was an AP English and Research teacher for seven years. In 2020 he was named Massachusetts Teacher of the Year—yet after winning the award, he decided to leave the classroom in 2021. We discuss Takeru’s early school experiences in Japan and New Jersey, how he become an educator through Teach For America, the daily realities of teaching in a “turnaround school,” the amazing AP classes he offered, the Teacher of the Year nomination, pandemic burnout, and the decision to leave his teaching position. We also speak more broadly about the purpose of education, schooling’s conne ..read more

Shortly after college, Jack Schott hit the road for two years to visit over 200 summer camps across the United States. He then co-founded a children’s sleepaway camp in upstate New York, Camp Stomping Ground (campstompingground.org), designed to inspire “radical empathy.” After co-directing Stomping Ground for many years (with Laura Kriegel) and consulting for other camps, Jack possesses a wealth of knowledge about the power and possibility of sleepaway camps. We discuss the unique magic that camps create, what kind of camps exist in the United States, how they promote self-directed learning ..read more

Nate Singer is the Managing Director of Mission Holdings, a father of two, and the guy who first got me interested in alternative education. We discuss his early struggles at boarding school, getting rejected to UC Berkeley (but successfully appealing the decision), working hard as a math major, second-guessing conventional teaching methods, creating a class about educational television (where he and I met), John Taylor Gatto, and encouraging Berkeley students to question mainstream pedagogy. After college Nate moved into the world of finance in a quest for broader impact and understanding the ..read more

Michelle Bruce is a mother of 4 who (along with her husband John) has been “boatschooling” since 2013. We discuss the evolution of her eclectic homeschooling approach, the family’s slow travel philosophy, the boat’s life-support systems and operating expenses, her kids’ “rollercoaster” social life, her impressions of the worldschooling community, what happened during the pandemic, and the judgment she received from other parents for raising her family at sea. Recorded on the boat in Sant Carles de la Rápita, Spain, Oct 31, 2021 ..read more

Seth Frey (enfascination.com) is a professor of Communication at UC Davis who focuses on the science of self-governance. We discuss our shared history in the Berkeley Student Cooperatives, Seth’s experience living in communities ranging from 4 to 400 members, his research on Minecraft and World of Warcraft communities, why benevolent dictators are surprisingly common, why children (and adults!) are surprisingly bad at self-governance, the Lord of the Flies stereotype, and how we might grant young people more genuine opportunities to manage their own worlds. Learn more about the Unschool Advent ..read more