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Blake Boles Podcasts

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Off-Trail Learning

Blake Boles

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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.
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Self Directed

Cecilie & Jesper Conrad

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Self Directed - A Podcast on Life, Learning, and Raising Free Thinkers. Hosts Cecilie and Jesper Conrad, full-time travellers since 2018 and parents of four, invite a new guest on the podcast every Thursday.
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The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hu ...
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Send us a text Blake Boles joins us to talk about his recent editorial, "I Don't Want a Nuclear Family, I Want a Galactic Commune - on the pursuit of quality conversation", which is about the decline of quality conversation and his resistance to the nuclear family model. We discuss the difference between daily logistics and real dialogue, why trave…
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In this episode, I talk with Dennis Owen about his journey from a long career in the airline industry to building a purposeful and active retirement in Chiang Mai, Thailand. Dennis shares how he intentionally “retired to” a new life filled with volunteering, consulting, and community involvement, rather than just leaving work behind. We discuss the…
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Send us a text Adolescence is often seen as something to endure — awkward years full of turbulence and struggle. But what if these years could be a time of discovery, adventure, and growth? In this episode, Jesper and Cecilie Conrad talk with Chris Balme on the launch day of his new book, Challenge Accepted: 50 Adventures to Make Middle School Awes…
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Send us a text How can we recover the essential human connections that make life meaningful and sustainable? How can we create a world where neighbors know each other's names, children play freely outdoors, and no parent faces the overwhelming challenges of raising children alone? Sarah van Gelder, founder of YES Magazine and author of "The Revolut…
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Send us a text In this episode, we talk with Ben Feliz (14) and Addison Harding (13), home-educated children and contributors to the anthology “Hidden Voices Speak.” Addison came up with the idea for the book, Ben designed the cover, and they worked together with others to publish it. Both care deeply about children’s rights and wanted to respond t…
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In this video, I talk with Rekha about Boundless Life and the idea of location-independent education. We cover her background, what led her to start Boundless Life, and how the program works for families who want a different approach to learning and community. For more: Boundless Life Boundless Education Rekha on LinkedIn Rekha on Instagram (00:00)…
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Send us a text We sit down with Andrew and Heidi Schrum, just three weeks away from starting their life as a full-time nomadic worldschooling family. They ask us direct questions about our seven years of unschooling and worldschooling. We discuss how the biggest changes happened in us as parents—not our children. We describe letting go of academic …
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In this episode, I interview my friend Pranab Saachi, and we get specific about the ideas and influences that have shaped his thinking. We talk about codependent origination from Buddhist philosophy, the concept of “quake books” that have shifted his worldview, and his own approach to “attentional co-piloting” as a practical alternative to traditio…
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Send us a text We sit down with Heidi and Andrew Schrum, who are about to leave home and begin travelling full-time with their two young children. They ask us what we wish we’d known at the beginning, and we talk through everything from reluctant kids and screen time to preparation that doesn’t help and the emotional crash that often comes six mont…
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In this episode, I'm pumped to welcome back Nick Maggiulli to the podcast (https://youtu.be/deMXbaI-Ir4). We dive into various topics about money and financial independence, with a focus on Nick's endorsement of the 'COAST Fire' strategy, something I accidentally embraced after quitting my job. Nick shares his personal stories of financial challeng…
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Luke’s conversation with Sam MacIlwaine, who contributed the poem “Dirtbag” to Volume 25 of The Climbing Zine, and is also featured on the back cover of that issue. Subscribe/ score some books/clothes/stickers: https://shop.climbingzine.com/ Our sponsors for Season 7: Kilter: http://settercloset.com (email [email protected] for more information…
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Send us a text Charles Eisenstein is an author and speaker whose books and essays explore themes of community, human connection, economics, and social change. He is known for works such as The More Beautiful World Our Hearts Know Is Possible. Charles joins us to explore how modern family structures have evolved and what's been lost in our transitio…
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Send us a text What if our traditional education system is fundamentally misaligned with how humans naturally learn? Jesper and Cecilie Conrad continue their conversation with Jamie Rumble, exploring the philosophy and practice of unschooling within a nomadic lifestyle. Jamie shares how his background, including influences from Paulo Freire and the…
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Lawrence is one of my favorite creators. He shares with passion, vulnerability and care. I chatted with Lawrence Yeo about his new book, 'The Inner Compass,' exploring themes of self-reflection, creativity, and the journey of writing and self-publishing. We discuss the importance of engaging with the world to gain a deeper understanding of oneself,…
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To kick off Luke’s summer climbing road trip, he stopped in Moab, Utah for this conversation with Mary Eden, also known as the Trad Princess. Our sponsors for Season 7: Kilter: http://settercloset.com (email [email protected] for more information) Scarpa: www.scarpa.com Osprey: https://www.osprey.com/ Subscribe/ score some books/clothes/sticker…
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Send us a text We got an email from Jamie Rumble... "I’m a Master of Education student at Cape Breton University, Nova Scotia, Canada. For my thesis, I’m researching how digital nomads are adapting their lifestyles in response to climate change, and what insights their experiences might offer for future education and planetary citizenship." We thou…
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In this episode, I have a conversation with my friend Jack Moses. Three years ago, Jack emailed me after reading my book, declaring he was dropping out of college. Over time, I've been amazed by his life's actions, from embracing hustle culture to diving deep into spirituality. Recently, Jack led a retreat in Thailand, inspiring me with his courage…
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Send us a text What happens when a single mom chooses to reject conventional norms, embraces van life, and takes her daughter out of traditional education? Vanessa Woozley joins us to share her inspiring story of courage, resilience, and transformation. Vanessa’s adventure began with short trips, gradually evolving into full-time worldschooling in …
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Send us a text When Jack Stewart turned off the internet, he discovered that digital connection often acts as a “social appetite suppressant”—satisfying on the surface, but not deeply nourishing. In this conversation, Jack explains how removing online distractions led him to seek out in-person connection, from literally knocking on neighbors’ doors…
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Send us a text Sociologist Jennie Germann Molz joins the podcast to discuss her book The World Is Our Classroom: Extreme Parenting and the Rise of Worldschooling. Jennie is a professor at the College of the Holy Cross whose research explores mobility, technology, and alternative forms of family life. Drawing on both academic insight and her own exp…
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Send us a text After her eight-year-old son was expelled from school in the UK, Corianda Shepherd and her partner Joel left behind a life that no longer worked. They moved to rural Spain, bought the first house they saw, and slowly built Shepherd’s Rest—a worldschooling community where families live together, learn in nature, and reject the idea th…
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Personal updates about life, including his recent move back to Asia, reflections on work and career paths, parenting experiences, and insights into education and self-publishing. I share the challenges and joys of parenting, how I think about decisions in regards to kids, and evolving thoughts on publishing and creative projects. Topics 00:00 Intro…
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Send us a text What if the real magic happens not when you push harder, but when you let go? We explore surrender as a powerful, often misunderstood key to living a fuller life. Kute Blackson is a transformational teacher and bestselling author of The Magic of Surrender. Known for his dynamic presence and multicultural background, he’s guided thous…
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Send us a text In this episode, we explore how modern culture has stripped childhood of the freedom it needs to thrive—and what can be done to bring it back. Our guest is Lenore Skenazy, author of Free-Range Kids and co-founder of the nonprofit Let Grow, launched with Jonathan Haidt, Peter Gray, and Daniel Shuchman to champion independence, resilie…
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Send us a text What happens when your child simply won't fit inside society's educational box? When Anna Vestlev Sandfeld realized her son didn’t fit into the structure of kindergarten—and likely never would fit into traditional school—she and her husband chose unschooling. In this conversation with her cousin Cecilie and co-host Jesper, Anna refle…
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Hello! I'm back! Expect a slow ramp, but there are new episodes coming! I talked with Nat Eliason about his journey as a writer, from early experiments with ideas to fully embracing writing as a career. We discussed the challenges and rewards of moving from nonfiction to fiction, the trade-offs between traditional and self-publishing, and the impor…
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Another conversation where Luke is the guest. This episode is from the “Dirtbag Rich” podcast, hosted by Blake Boles. Our sponsors for Season 7: Kilter: http://settercloset.com (email [email protected] for more information) Scarpa: www.scarpa.com Osprey: https://www.osprey.com/ Subscribe/ score some books/clothes/stickers: https://shop.climbing…
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Send us a text Outschool founder Amir Nathoo explains why education built on passion—not curriculum—may be the only way to truly prepare kids for a rapidly changing world. We talk about his shift from traditional schooling in the UK to building Outschool, how becoming a parent deepened his beliefs, and why interest-led learning offers more than jus…
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The tables are turned on our host, Luke Mehall, as we share this episode of his appearance on The Struggle Climbing Show, hosted by Ryan Devlin. Our sponsors for Season 7: Kilter: http://settercloset.com (email [email protected] for more information) Scarpa: www.scarpa.com Osprey: https://www.osprey.com/ Subscribe/ score some books/clothes/stic…
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Send us a text Ever wondered what life could look like if you broke free from the conventional 9-5? David Cole and his family sold their home in Chicago in 2019 and haven’t stopped moving since. Cecilie and Jesper talk with him about how they made the shift from occasional travellers to full-time nomads. "I think what stopped us the most was mindse…
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Send us a text Dr. Cam joins us to discuss parenting teenagers and why efforts to control them often create more distance. She explains how control can undermine trust and why focusing on connection leads to better results. We discuss the difference between respect and obedience, and how letting teens say “no” builds confidence and self-trust. Jesp…
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Send us a text In this conversation with author and speaker Jacob Nordby, we explore the paradox of freedom in modern life. Is it simply doing whatever we want—or does real freedom require something deeper? While many consider freedom to be about doing whatever they want without constraints, Jacob challenges this perception. "A lot of people assume…
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Send us a text Yasmin and Andy left a comfortable life in the UK to join a small off-grid community in the jungles of Belize. Fifteen years after cycling through Central America, Yasmin and Andy returned—this time with three kids and a desire for a different kind of life. What began as a plan to visit intentional communities in Europe shifted durin…
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Send us a text In this episode, we speak with Amanda Diekman about how her parenting changed when her six-year-old son went into autistic burnout. He lost verbal communication, stopped eating most foods, and couldn't follow basic routines. Faced with a crisis, Amanda chose to stop trying to fix him and instead removed demands to create safety. She …
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Send us a text Luz and David from Evolving Education left careers in biotechnology to explore and document alternative education models worldwide. Frustrated by rigid schooling systems, they traveled to over 170 learning centers to understand how children learn best outside the traditional classroom. In this episode, we talk about how compulsory sc…
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Send us a text Iris Chen, author of Untigering: Peaceful Parenting for the Deconstructing Tiger Parent, shares how she shifted from a strict, high-expectation parenting style to a trust-based approach. Raised in a Chinese-American household, Iris grew up with academic pressure and obedience as the norm. She carried those expectations into her own p…
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Links: Podcast Blake Boles Dirtbag Rich Site: https://www.blakeboles.com/dbr/ Episode Desription Paul Millerd is a 39-year-old writer, ex-consultant, and advocate for ditching the default path in favor of what he calls “the pathless path.” (pmillerd.com / @p_millerd) Paul walked away from a promising corporate consulting career—think McKinsey, pres…
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Send us a text The moment you carve, knit, bake or start folding paper, something remarkable happens in your brain. The anxious spiral of thoughts quiets, stress hormones recede, and you enter a state that Dr. Anne Kirketerp calls "meaningful self-forgetfulness." Dr. Anne Kirketerp is a psychologist, researcher, and craftsperson who pioneered Craft…
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