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PODCAST · education

Off-Trail Learning

by Blake Boles

Interviews with innovative educators, self-directed young people, and others who think differently about learning, teaching, and schooling. Hosted by Blake Boles (blakeboles.com), author of "Why Are You Still Sending Your Kids to School?" and founder of Unschool Adventures.

Publisher-supplied feed metadata · PodParley refreshed Sep 4, 2026 · Source feed

Episodes

  1. Introducing: Dirtbag Rich

    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...

  2. Blake Boles on Adventure

    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...

  3. Chris Balme on Finding the Magic in Middle School

    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…

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  4. Liam Nilsen on Reading

    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...

  5. Grace Llewellyn on The Teenage Liberation Handbook, 3rd Edition

    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...

  6. Takeru Nagayoshi on Walking Away from "Teacher of the Year"

    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...

  7. Jack Schott on Why Summer Camps Matter

    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...

  8. Nate Singer on Questioning Education at Berkeley and Learning through Entrepreneurship

    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,...

  9. Michelle Bruce on Boatschooling

    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…

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  10. Seth Frey on Self-Governed Youth Communities

    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…

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  11. Manue on The Homeschooling Situation in France

    Manue is a representative in the South of France of Les Enfants D’Abord (lesenfantsdabord.org), a home education advocacy association which is particularly committed to the rights of unschoolers. (The name translates to “Children First.”) We discuss the organization’s mission to promote…

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  12. Nick Bergson-Shilcock on the Recurse Center

    Nick Bergson-Shilcock is the CEO and co-founder of the Recurse Center (recurse.com), a self-directed and community-driven educational retreat for computer programmers. Nick describes his background as a lifelong unschooler (he’s the son of Peter Bergson, a recent podcast guest), as well as his...

  13. Anna Smith and Mara Donahoe on Home & Hybrid Education

    Anna Smith and Mara Donahoe are the co-founders (with Natasha Morisawa) of the National Association of Home & Hybrid Education (homeandhybrideducation.org), a new advocacy organization that hopes to bring together all members of the alternative education movement in the United States. We discuss...

  14. Lilli and Elena on Biking Through Europe at Age 19

    While biking through the south of France, I met Lilli and Elena, two 19-year-old German women who are also on a cycling adventure. (We shared the same Couchsurfing host.) We discuss their bike trip, their path through formal education in Germany, why they’re taking a gap year, how they spend less...

  15. Joel Malkoff on Joining The Circus

    Joel Malkoff (joelkmalkoffcircusartist.com) is a contemporary circus artist and 27-year-old grown unschooler from Indiana. We discuss Joel’s recent experience at the National Circus School of Montreal (“the Harvard of circus”), the job market for circus artists, and his new 3-person circus...

  16. Alfie Kohn on Progressive Education

    Alfie Kohn (alfiekohn.org) is the author of fourteen books and a well-known advocate of progressive education. Mr. Kohn discusses the purpose behind his 30+ years of advocacy, his critique of “grit” and “growth mindset”, and his take on the classic progressive school models...

  17. Catherine Fraise on Workspace

    Catherine Fraise is the founder of Workspace Education (workspaceeducation.org) and 100 Roads (100roads.org). We discuss Catherine’s background as a Montessori educator, the pivotal trip to Japan she took as a 12-year-old, the Workspace co-learning and co-working center she created in…

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  18. Peter Bergson on Open Education

    Peter Bergson is the co-founder of two self-directed learning centers in the Philadelphia area: Open Connections (openconnections.org) and Natural Creativity Center (naturalcreativity.org). We discuss Peter’s journey from creativity consultant to early childhood educator, his collaboration with...

  19. Pat Farenga on the Post-Pandemic Future of Homeschooling (Part 2) + the Harvard Homeschool Summit

    Pat Farenga returns to talk about the second half of Harvard’s “Post-Pandemic Future of Homeschooling” conference, after which we discuss a different, secret, *invite-only* Harvard summit (hosted by Elizabeth Bartholet and James Dwyer) that proposed extremely restrictive reforms to homeschooling...

  20. Pat Farenga on the Post-Pandemic Future of Homeschooling (Part 1)

    In this special two-part discussion, Pat Farenga and I discuss Harvard University’s ongoing 7-week conference, the “Post-Pandemic Future of Homeschooling.” This free online conference brings together researchers and academics in the field of homeschooling, and Pat and I are here to share what...

  21. Debbie Reber on Differently Wired Kids

    Debbie Reber (debbiereber.com) is the author of Differently Wired: Raising an Exceptional Child in a Conventional World and the founder of TiLT Parenting (tiltparenting.com), a podcast and online community. We discuss how Debbie coaches parents on issues of neurodivergence, the challenges that...

  22. Olivia Barnes on Self-Directing as a 16-Year-Old

    Olivia Barnes (blacklifeblueworld.wixsite.com/blbwofficialwebsite) has always had a somewhat unconventional education, but after a frustrating year at a well-regarded performing arts school, she decided to take the reins of her education. We discuss Olivia’s decision to spend her 10th grade year...

  23. Blake's Sabbatical Update

    Rivers and bike trips and workshops, oh my! A quick update from my somewhat-successful-sabbatical. Also: new podcast episodes coming soon!

  24. Blake Goes on Sabbatical

    Off-Trail Learning is on hiatus! In this brief personal update, I discuss my decision to go on sabbatical in 2021. Learn more at (newly redesigned) blakeboles.com.

  25. Kevin Currie-Knight on Self-Directed Learning in College

    Kevin Currie-Knight (kevinck.net) is a philosopher, historian of education, and Teaching Associate Professor at East Carolina University’s College of Education. Following a stint as a high school special educator, Kevin began training future public school teachers at the college level and...

  26. Martina Geromin on Self-Directed Learning in Europe

    Martina Geromin is the CEO and Co-Founder of School Beyond Limitations (school-beyond-limitations.com). Originally from Italy, Martina has lived and worked in Austria, Switzerland, and the United Kingdom. We discuss the state of self-directed education in Europe (including homeschooling and...

  27. Naomi Fisher on Whether Parents Matter

    Dr. Naomi Fisher is a clinical psychologist, mother of two self-directed learners, and the author of the forthcoming book, "Changing Our Minds: How children can take control of their own learning." In this deep-dive interview, Naomi and I dissect the modern culture of “intensive parenting” and…

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  28. Dev Carey on Helping Young Adults Grow Up with a Gap Year

    Dev Carey is the founder and co-director of the High Desert Center in Paonia, Colorado (highdesertcenter.org), where he’s been offering an adventurous, affordable, and highly alternative gap year program for more than six years. We discuss his approach to working with 16- to 23-year-olds, the…

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  29. Victoria Ransom on Prisma

    Prisma (joinprisma.com) is a brand-new company that’s attempting to combine the best parts of homeschooling with the best parts of online education. In this episode I speak with Victoria Ransom, who co-founded Prisma alongside her husband Alain Chuard, about the Prisma model, who it’s for, how...

  30. Alexander Khost on Education as a Political Act

    What does it mean to educate in freedom? What are the different flavors of “freedom” that appear in the self-directed education world? In this live interview (recorded in January 2020) I speak with Alexander Khost, Editor-in-Chief of Tipping Points, the online magazine of The Alliance for...

  31. Ethan Mitchell on Being a Polymath

    What’s it like to be someone who knows a little bit about everything? Or sometimes, a *lot* about everything? Ethan Mitchell (zemita.net) is a teacher and essayist who lives on a sheep farm in Vermont, attended just one semester of college, and writes an underground newsletter called the...

  32. Kristen Montesano on Giftedness in Self-Directed Education

    If you have a kid who has been identified as academically gifted, is a self-directed learning center a good place for them? Kristen Montesano, co-founder of EPIC Life Learning Community in Dallas, Texas (epiclifelearningcommunity.com), grew up in public school gifted programs, yet she was still...

  33. Elizabeth Bartholet And Rachel Coleman On Homeschooling’s Potential For Abuse

    In May 2020, Elizabeth Bartholet, a Harvard Law Professor, called for significant new regulations on homeschooling in the United States. In this extra-long episode, I interview Professor Bartholet about her ideas, research, and proposals. We are joined by Rachel Coleman, executive director of the...

  34. Aaron Eden on Re-humanizing Education

    Many teachers aspire to work at progressive schools that are more kind, individualized, and humane. But what do you do when even the “best schools” still treat kids with distrust and coercion? Aaron Eden has asked this question over his long career in education, ultimately leading him to his...

  35. Blake Boles & Kevin Currie-Knight on Why Are You Still Sending Your Kids to School?

    This special episode celebrates the release of Blake’s new book, Why Are You Still Sending Your Kids to School?, which is now available through local bookstores, Amazon.com, and other marketplaces. Joined by guest host Kevin Currie-Knight, Blake discusses how kids learn to work hard when given…

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  36. Jim Dwyer on Homeschooling Philosophy, Law, and Regulation

    James Dwyer is a professor of law at William & Mary Law School and the co-author of Homeschooling: The History & Philosophy of a Controversial Practice (University of Chicago Press, 2019). Following the arc of Jim’s excellent book (co-authored with historian Shawn Peters), we discuss some...

  37. Zoe Greenhouse on Hiking the PCT Instead of Going to High School

    17-year-old Zoe Greenhouse (zoegreenhouse.com) talks about her recent decision to stop going to school and attempt a thru-hike of the 2,650-mile Pacific Crest Trail (PCT). Zoe discusses her background as an unschooler and world-schooler, the handful of private and public schools she attended, her...

  38. Maya Landers on Postponing College (Perhaps Forever)

    Maya Landers (mayalanders.com) is a 22-year-old lifelong unschooler from Austin, Texas, who always thought she would go to college to study English. Yet at 17 she opted to take a gap year… followed by another gap year… which turned into another gap year…. and yet another! We discuss Maya’s...

  39. Matthew Gioia on Sudbury Ideals vs. Reality

    After teaching 6th grade reading at a tough school in Mississippi, Matthew Gioia discovered the Sudbury Valley School literature and quickly became enamored. Like many people (myself included) Sudbury represents an idyllic philosophy that leaves behind the baggage of conventional education. But…

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  40. Kerry McDonald on Entrepreneurial Education

    Kerry McDonald (fee.org/kerry) is the author of the 2019 book, Unschooled: Raising Curious, Well-Educated Children Outside the Conventional Classroom, as well as a regular contributor to Forbes, the Cato Institute, and the Foundation for Economic Education. We discuss Kerry’s faith in the private...

  41. Gina Riley on Self-Determination Theory

    Gina Riley, Ph.D., is an educational psychologist and Clinical Professor of Adolescent Special Education at Hunter College in New York City. She's also the leading researcher on the connection between unschooling and Self-Determination Theory. Gina discusses the three factors that generate...

  42. Ken Danford on Liberated Learners

    Ken Danford is the Executive Director of North Star (northstarteens.org), author of the new book "Learning is Natural, School is Optional", and the first guest to ever appear on this podcast. In this episode we discuss the Liberated Learners network through which Ken helps other people start...

  43. Lori Walker on Village Home

    What if there was a community college built just for homeschoolers? This may not exist yet, but Lori Walker has created the next best thing: Village Home Education Resource Center (villagehome.org). For 17 years Village Home has served young people (from pre-k through high school) in and around...

  44. Bill Deresiewicz on The Power and Peril of Self-Education

    What does it mean to “self-educate?” Are autodidacts made or born? Can one develop an intellect without formal higher education? In this special episode, Blake discusses these big questions (and many more) with Bill Deresiewicz (the author of Excellent Sheep) and guest facilitator Dev Carey. This...

  45. Antonio Buehler on Competitive College Admissions for Non-Traditional Students

    Antonio Buehler was the first person in his family to finish high school or attend college. After completing an MBA at Stanford he went into investment banking and private equity before becoming deeply impressed by homeschooling and creating his own self-directed learning center in Austin, Texas,...

  46. Blake Boles on the Future of Alternative Education

    Where is the alternative education movement headed, and how will we arrive there? In this special episode, Blake gives the closing keynote at the AERO (Alternative Education Resource Organization) conference in Portland, Oregon on June 29th, 2019. Themes of the talk include: embracing the growing...

  47. Margie Sanderson on Children's Rights

    What are "children's rights" and how do they overlap with the world of self-directed learning? Margie Sanderson, a 24-year-old board member of the National Youth Right Association (youthrights.org), talks with me about the different conceptions of children's rights (also called youth rights), the...

  48. Ted Dintersmith on Innovative Schools

    After a successful career as a venture capitalist, Ted Dintersmith (teddintersmith.com)dedicated himself to discovering highly innovative schools around the United States, leading him to produce the 2015 documentary, Most Likely to Succeed, and his 2018 book, What School Could Be. Ted and I…

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  49. Blake Boles on Quitting High School

    If conventional high school isn't a good fit for your kid, what should you do -- push harder, or try something new? Is high school mandatory for college, career, and a successful transition to adulthood? In this special episode, recorded live at the CHN Family Expo conference in southern…

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  50. Jerry Mintz on AERO

    Jerry Mintz founded the Alternative Education Resource Organization (AERO) over 30 years ago and has since helped start over 50 learner-centered schools. In this special episode, Jerry and I interview each other about the state of alternative education in the world and what makes us hopeful that...

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ABOUT THIS SHOW

Interviews with innovative educators, self-directed young people, and others who think differently about learning, teaching, and schooling. Hosted by Blake Boles (blakeboles.com), author of "Why Are You Still Sending Your Kids to School?" and founder of Unschool Adventures.

HOSTED BY

Blake Boles

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Frequently Asked Questions

How many episodes does Off-Trail Learning have?

Off-Trail Learning currently has 104 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Off-Trail Learning about?

Interviews with innovative educators, self-directed young people, and others who think differently about learning, teaching, and schooling. Hosted by Blake Boles (blakeboles.com), author of "Why Are You Still Sending Your Kids to School?" and founder of Unschool Adventures.

How often does Off-Trail Learning release new episodes?

Off-Trail Learning publishes regularly with 104 episodes available. Check the episode list for the typical release schedule.

Where can I listen to Off-Trail Learning?

You can listen to Off-Trail Learning on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Off-Trail Learning?

Off-Trail Learning is created and hosted by Blake Boles.
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