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Off-Trail Learning

103 EpisodesProduced by Blake BolesWebsite

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

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Blake Boles on Adventure

September 11th, 2022


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 …

Chris Balme on Finding the Magic in Middle School

August 15th, 2022


Chris Balme ( is the founding head of school of The Millennium School and the author of Finding the Magic in Middle School. After …

Liam Nilsen on Reading

July 13th, 2022


Liam Nilsen ( is a designer and educator based in Åårhus, Denmark. He’s a former member of the LEGO Idea Studio, the founder of an …

Grace Llewellyn on The Teenage Liberation Handbook, 3rd Edition

June 10th, 2022


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, …

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

May 13th, 2022


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 …

Jack Schott on Why Summer Camps Matter

April 18th, 2022


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 …

Nate Singer on Questioning Education at Berkeley and Learning through Entrepreneurship

March 17th, 2022


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 …

Michelle Bruce on Boatschooling

February 7th, 2022


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 …

Seth Frey on Self-Governed Youth Communities

January 12th, 2022


Seth Frey ( 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 …

Manue on The Homeschooling Situation in France

December 13th, 2021


Manue is a representative in the South of France of Les Enfants D’Abord (, a home education advocacy association which is …

Nick Bergson-Shilcock on the Recurse Center

November 7th, 2021


Nick Bergson-Shilcock is the CEO and co-founder of the Recurse Center (, a self-directed and community-driven educational retreat for computer programmers. Nick describes his background as a lifelong …

Anna Smith and Mara Donahoe on Home & Hybrid Education

October 20th, 2021


Anna Smith and Mara Donahoe are the co-founders (with Natasha Morisawa) of the National Association of Home & Hybrid Education (, a new advocacy organization that hopes to bring together …

Lilli and Elena on Biking Through Europe at Age 19

October 12th, 2021


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 …

Joel Malkoff on Joining The Circus

September 11th, 2021


Joel Malkoff ( is a contemporary circus artist and 27-year-old grown unschooler from Indiana. We discuss Joel’s recent …

Alfie Kohn on Progressive Education

August 23rd, 2021


Alfie Kohn ( 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 …

Catherine Fraise on Workspace

August 1st, 2021


Catherine Fraise is the founder of Workspace Education ( and 100 Roads ( We discuss Catherine’s background as a Montessori educator, the pivotal trip to Japan she took as a …

Peter Bergson on Open Education

July 19th, 2021


Peter Bergson is the co-founder of two self-directed learning centers in the Philadelphia area: Open Connections ( and Natural Creativity Center ( We discuss Peter’s journey …

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

June 25th, 2021


Pat Farenga returns to talk about the second half of Harvard’s “Post-Pandemic Future of Homeschooling” conference, after which we discuss a …

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

June 1st, 2021


In this special two-part discussion, Pat Farenga and I discuss Harvard University’s ongoing 7-week conference, the “Post-Pandemic Future of …

Debbie Reber on Differently Wired Kids

May 26th, 2021


Debbie Reber ( is the author of Differently Wired: Raising an Exceptional Child in a Conventional World and the founder of TiLT Parenting (, a podcast and online community. We discuss …

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

May 5th, 2021


Olivia Barnes ( has always had a somewhat unconventional education, but after a frustrating year …

Blake's Sabbatical Update

April 24th, 2021


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

Blake Goes on Sabbatical

December 13th, 2020


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) …

Kevin Currie-Knight on Self-Directed Learning in College

December 10th, 2020


Kevin Currie-Knight ( is a philosopher, historian of education, and Teaching Associate Professor at East Carolina University’s College of …

Martina Geromin on Self-Directed Learning in Europe

November 20th, 2020


Martina Geromin is the CEO and Co-Founder of School Beyond Limitations ( Originally from Italy, Martina has lived and …

Naomi Fisher on Whether Parents Matter

October 25th, 2020


Dr. Naomi Fisher is a clinical psychologist, mother of two self-directed learners, and the author of the forthcoming book, "Changing Our Minds: How …

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

October 1st, 2020


Dev Carey is the founder and co-director of the High Desert Center in Paonia, Colorado (, where he’s been offering an …

Victoria Ransom on Prisma

September 11th, 2020


Prisma ( is a brand-new company that’s attempting to combine the best parts of homeschooling with the best parts of online education. …

Alexander Khost on Education as a Political Act

August 12th, 2020


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, …

Ethan Mitchell on Being a Polymath

July 25th, 2020


What’s it like to be someone who knows a little bit about everything? Or sometimes, a *lot* about everything? Ethan Mitchell ( is a teacher and essayist who lives on a sheep farm in Vermont, attended just one …

Kristen Montesano on Giftedness in Self-Directed Education

June 25th, 2020


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 …

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

June 6th, 2020


In May 2020, Elizabeth Bartholet, a Harvard Law Professor, called for significant new regulations on homeschooling in the United States. In this …

Aaron Eden on Re-humanizing Education

May 27th, 2020


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” …

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

May 15th, 2020


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 …

Jim Dwyer on Homeschooling Philosophy, Law, and Regulation

April 19th, 2020


James Dwyer is a professor of law at William & Mary Law School and the co-author of Homeschooling: The History & Philosophy of a …

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

March 21st, 2020


17-year-old Zoe Greenhouse ( talks about her recent decision to stop going to school and attempt a thru-hike of the 2,650-mile …

Maya Landers on Postponing College (Perhaps Forever)

February 17th, 2020


Maya Landers ( is a 22-year-old lifelong unschooler from Austin, Texas, who always thought she would go to college to study English. …

Matthew Gioia on Sudbury Ideals vs. Reality

January 23rd, 2020


After teaching 6th grade reading at a tough school in Mississippi, Matthew Gioia discovered the Sudbury Valley School literature and quickly became …

Kerry McDonald on Entrepreneurial Education

January 8th, 2020


Kerry McDonald ( is the author of the 2019 book, Unschooled: Raising Curious, Well-Educated Children Outside the Conventional …

Gina Riley on Self-Determination Theory

December 10th, 2019


Gina Riley, Ph.D., is an educational psychologist and Clinical Professor of Adolescent Special Education at Hunter College in New York City. She's …

Ken Danford on Liberated Learners

November 13th, 2019


Ken Danford is the Executive Director of North Star (, author of the new book "Learning is Natural, School is Optional", and the …

Lori Walker on Village Home

October 3rd, 2019


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 …

Bill Deresiewicz on The Power and Peril of Self-Education

September 4th, 2019


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 …

Antonio Buehler on Competitive College Admissions for Non-Traditional Students

August 9th, 2019


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 …

Blake Boles on the Future of Alternative Education

July 14th, 2019


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 …

Margie Sanderson on Children's Rights

June 20th, 2019


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 …

Ted Dintersmith on Innovative Schools

May 29th, 2019


After a successful career as a venture capitalist, Ted Dintersmith ( himself to discovering highly innovative schools …

Blake Boles on Quitting High School

May 5th, 2019


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 …

Jerry Mintz on AERO

March 5th, 2019


Jerry Mintz founded the Alternative Education Resource Organization (AERO) over 30 years ago and has since helped start over 50 learner-centered …

Ned Johnson on The Self-Driven Child

February 2nd, 2019


What’s the sense and science behind giving kids more control over their lives? Why do they deserve autonomy? Ned Johnson answers these questions in …

Kate Friedman on Promoting Self-Direction in Public Education

January 2nd, 2019


If you’re in love with the principles of self-directed learning but don’t want to abandon the public school system, how can you still make an impact? …

A Brief Introduction to North Star: Self-Directed Learning for Teens

December 5th, 2018


North Star ( is an alternative to middle school and high school in Western Massachusetts, and it's a highly inspiring model of …

T.K. Coleman on the Best Arguments Against College

November 11th, 2018


What are the best and worst arguments for going to 4-year college today? On today’s episode I debate this question with T.K. Coleman, the Education …

Matt Sanderson on Not Back to School Camp

October 28th, 2018


If you’re a teenager who (1) doesn’t go to conventional school and (2) wants to make new, open-minded friends — then get yourself to Not Back to …

Cassidy Younghans on Building a Career in Self-Directed Education as a Twenty-Something

October 11th, 2018


If you want to get involved in alternative education in your twenties, what steps can you take to make it possible? Cassidy Younghans, age 27, is …

Pat and Chandra Montgomery on Clonlara

September 22nd, 2018


What was it like to start an alternative school—especially one that supports “homeschoolers”, a hitherto unknown term—back in the sixties and …

Blake Boles and Zen Zenith on Unschool Adventures

August 11th, 2018


In this special episode, Zen Zenith interviews Blake Boles about the past, present, and future of Unschool Adventures (, …

Joel Hammon on Quitting Teaching

July 26th, 2018


After a decade of teaching at public and private schools, Joel Hammon quit. Despite being on track to earning a six-figure salary with full benefits, …

Peter Gray on the Evidence for Self-Directed Education

July 5th, 2018


Does self-directed education really “work,” and how can we prove it? In this episode I speak with Peter Gray, Ph.D., about the evidence (and lack …

Jade Rivera on Neurodivergence

June 22nd, 2018


Gifted, twice-exceptional, autistic, ADD, dyslexic: each of these labels falls under the umbrella of “neurodivergence”, and each has served to inspire thousands of families to consider self-directed learning options. …

Gabe Cooper on Starting a Public “Unschool”

June 7th, 2018


Many dream of combining the principles of unschooling with the resources of public school — and Gabe Cooper is one of those few who has actually done …

Bryan Caplan on the Value of Conformity

May 19th, 2018


How much of school is about skill-building and how much is about signaling, i.e., proving to employers that you’re intelligent, diligent, and can …

Jim Wiltens on Deer Crossing Camp

April 23rd, 2018


Jim Wiltens is a modern-day Indiana Jones, an incredibly powerful teacher, and a huge figure in my life since age 11. I’m honored to finally get him …

Wes Beach on Building a One-Man High School

March 31st, 2018


Frustrated as a public high school teacher in Santa Cruz, California, Wes Beach started his own one-man high school, Beach High School (

Lisa Betts-LaCroix on Micro-schooling in the San Francisco Bay Area

March 16th, 2018


Lisa Betts-LaCroix, a homeschooling mother of two and co-founder of Bay Area Gifted Homeschoolers (, talks with Blake about the huge …

Blake Boles on What It Means to Be Educated

May 16th, 2017


On this special episode, I read from my new long-form article published by the Alliance for Self-Directed Learning ( In it I share my definition of …

The Argentina Semester on Living Abroad

March 30th, 2017


On this special episode, young adult participants on the Unschool Adventures Argentina Semester 2017 talk about the challenges of living and learning …

Tam Pham on Reaching Out to People

March 9th, 2017


Tam Pham ( is a 21-year-old college dropout, marketer in Silicon Valley, and author of How to Network and How to Land Your Dream …

The Unbearable Lightness of Being Victor Saad

February 7th, 2017


Victor Saad ( talks with host Blake Boles about the 12 apprenticeships that he did in 12 months instead of pursuing an MBA, the …

Catherine Gobron on Promoting Inclusivity in Self-Directed Learning

January 24th, 2017


Catherine Gobron, co-director of Lighthouse Holyoke (, a self-directed learning center for teenagers in western Massachusetts, …

Nathen Lester on the Challenges of Total Freedom

January 10th, 2017


Nathen Lester, a long-time advisor at Not Back to School Camp and soon-to-be-licensed Couples and Family Therapist, discusses the challenges that …

Mikala Streeter on Exposure

December 27th, 2016


Mikala Streeter, founder and principal of The LIFE School ( in Atlanta, Georgia, talks about her ambitious new progressive school …

Kevin Snavely on Unschooling in Alaska and Traveling the World

December 17th, 2016


23-year-old Kevin Snavely (skyping in from Bangkok) talks with Blake about being raised unschooled in Alaska, going back to public high school, the …

Caitlyn Scheel on Convincing Your Parents to Homeschool

December 1st, 2016


15-year-old Caitlyn Scheel talks with Blake about being bored in middle school, wanting to homeschool, and the summer she spent convincing her …

Sean Ritchey on Learning Through Work Instead of College

November 15th, 2016


29-year-old grown unschooler Sean Ritchey talks about his discussion to skip college in favor of starting his own design/build company. We discuss …

Milla von Tauber on Explaining Yourself as an Unschooler

November 2nd, 2016


18-year-old Milla Von Tauber talks with Blake about explaining yourself as a teenage unschooler, missing high school rites of passage, defining your …

Xander Macswan on Video Games

October 22nd, 2016


Xander Macswan, a 19-year-old grown unschooler, talks about growing up with unrestricted video game access. When do games hurt us, and when do they …

From Unschool to School to Unschool: A Conversation with Nikiah Childs

October 16th, 2016


Nikiah Childs grew up in elementary school, unschooled for 6 years, went back to a performance arts charter school, and then left school again to …

Steve Krouse on Dropping Out of College to Live the Silicon Valley Dream

October 9th, 2016


22-year-old Steve Krouse, co-founder of The Coding Space in New York City (, talks about his decision to leave his Computer …

Who Should Unschool and Who Shouldn't? A Conversation with Liam Nilsen

September 24th, 2016


Lifelong unschooler Liam Nilsen talks with Blake about the habits and mindset required for successful unschooling in the teenage years. And Liam asks …

Emma McCann on Going Back to School as an Unschooler

September 6th, 2016


23-year-old grown unschooler Emma McCann talks about making the decision to attend Buxton School, a progressive boarding school, instead of …

Grace Llewellyn on Not Back to School Camp

August 25th, 2016


Grace Llewellyn, author of The Teenage Liberation Handbook and executive director of Not Back to School Camp (, talks with Blake about her …

Dev Carey on the Perils of Goal-Setting

August 3rd, 2016


To be an effective self-directed learner, you have to be really good at setting goals...right? Maybe. Maybe not. In episode 21 of the Off-Trail Learning podcast, Dev Carey ( talks with Blake about the …

Help, I Don’t Know What I’m Doing With My Life! - A Conversation With Seraphina Mallon-Breiman

July 28th, 2016


Grown unschooler and recent college graduate Seraphina talks with Blake about deciding what to focus on after college, balancing money and meaning, …

Patrick Farenga On Self-Directed Learning

August 26th, 2015


Patrick Farenga, president of HoltGWS (, talks with host Blake Boles about homeschooling vs. unschooling vs. self-directed learning, …

Tomis Parker And Nancy Tilton On Agile Learning Centers

August 11th, 2015


Tomis Parker and Nancy Tilton talk with host Blake Boles about the Agile Learning Center framework (, Nancy’s school in …

Liam Nilsen On The Endor Initiative

July 28th, 2015


Liam Nilsen, founder of the Endor Initiative (, talks with host Blake Boles about his innovative program for self-directed …

Japhy Dhungana on The Value of Global Education

July 14th, 2015


Japhy Dhungana, program director at Where There Be Dragons (, talks with host Blake Boles about international semester …

Amy Milstein, Maya Milstein, And Maddy Platt On Unschooling in NYC

June 30th, 2015


Amy and Maya Milstein, mother and 14-year-old daughter of a New York City unschooling family, and Maddy Platt, their 16-year-old friend from Canada, …

William Deresiewicz On Excellent Sheep

June 16th, 2015


William Deresiewicz, author of Excellent Sheep and former English professor at Yale University, talks with host Blake Boles about the reaction to his …

Lucas Isakowitz On Unschooling, High School, And Alaskan Fishing

June 2nd, 2015


Lucas Isakowitz, a 24-year-old grown unschooler, college graduate, and part-time Alaskan fisherman, talks with host Blake Boles about his young life …

Ben Paul on Dropping Out of Law School in Germany

May 26th, 2015


Ben Paul, founder of the German social movement Anti-Uni (, talks with host Blake Boles about his decision to leave a prestigious law …

Misha Golfman on Wilderness Semesters

May 19th, 2015


Misha Golfman, founding director of Kroka Expeditions (, talks with host Blake Boles about leading unconventional semester-long wilderness …

Sophia Pink on Taking a High School Sabbatical

May 12th, 2015


Sophia Pink, a high school senior in Washington, DC (, talks with host Blake Boles about her decision to leave school for 10th grade …

Ivo Degn on Knowmads

May 5th, 2015


Ivo Degn, co-founder of Knowmads Spain (, talks with host Blake Boles about what it means to be a “knowmad”, stories from his time at the …

Ethan Knight on Gap Years

April 28th, 2015


Ethan Knight, executive director of the American Gap Association (, talks with host Blake Boles about the value of taking intentional …

Erik Werner On International Teen Travel

April 21st, 2015


Erik Werner, executive director of Global Works (, talks with host Blake Boles about creating service-focused international …

Isaac Morehouse on Praxis

April 14th, 2015


Isaac Morehouse, founder of Praxis (, talks with host Blake Boles about his 10-month program for 18- to 25-year-olds that combines …

Alan Webb And Sarah Jane Bradley On Creating Your Own Master's

April 7th, 2015


Alan Webb and Sarah Jane Bradley, organizers of the Open Master’s community (, talk with host Blake Boles about designing meaningful …

Michelle Jones on the Wayfinding Academy

March 31st, 2015


Michelle Jones, associate professor of Organizational Behavior and Leadership at Concordia University and founder of the Wayfinding Academy …

Will Richardson on Learning in the Internet Era

March 24th, 2015


Will Richardson, author of “Why School?” (, talks with host Blake Boles about information abundance, Minecraft, helping young …

Carsie Blanton on Unschooling

March 17th, 2015


Carsie Blanton, a singer-songwriter, blogger, and lifelong unschooler (, talks with host Blake Boles about making a living as a …

Kenneth Danford On Thriving Without School

March 12th, 2015


Kenneth Danford, executive director and co-founder of North Star: Self-Directed Learning for Teens (, talks with host Blake Boles …

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