Teaching Adventure
on running the school of my dreams
BIKING THROUGH THE SUN-DRENCHED VINEYARDS of southern France in October 2021, caffeinated and high on life, I asked myself: What am I capable of teaching?
I was thinking of John Taylor Gatto, the award-winning schoolteacher who quit his post in New York City public schools after 26 years to write about the problems inherent in modern education—and who subsequently inspired me to design my own undergraduate degree in alternative education theory.
One of Gatto’s concrete suggestions for education reform—one that initially rubbed me the wrong way—was that no one under 40 should be allowed to teach. Young teachers lack sufficient perspective and experience, Gatto argued. Let’s waive the college degree requirement, decertify the profession, and let anyone with something of value offer it… as long as they’re over 40.
I can argue both sides of that proposition. But on this breezy morning outside of Vaison-la-Romaine, in the middle of a 6-week, 5-country bike tour, I was suspending judgement and accepting Gatto’s provocative challenge. Next year, I turn 40. If this is when I might be capable of teaching something valuable to young people, what is it?
The answer came quickly: travel, adventure, and entrepreneurship.
These were the pursuits I’d studied, lived, and shared with young people for 15+ years already. If there’s anything I can teach, that’s it.
Pedaling faster with excitement, I continued my internal dialogue: Yes! I have something to offer the world! But how?
I’d already made plans to visit a new corner of Argentina—El Chaltén, in far southern Patagonia—just a few months later. There, I suspected, I might find a hostel to rent. And in this hostel, perhaps I could run an educational retreat for American teenagers, as I’d done a few times before. Why not make it a “Travel, Adventure, Entrepreneurship” retreat? My mind flew into trip-planning mode, and before long I was cooking up a new program.
The concept took twists and turns over the following seven months. I did find a hostel to rent in El Chaltén. But soon after that exploratory trip, I walked away from the idea entirely, feeling the concept too limited and fearing it would become a one-man-show. Then in early summer 2022, upon learning that two good friends (and former co-workers) were available to join me for 4 weeks to teach their respective domains of expertise, partner dance and foreign language, the vision coalesced. The Patagonia Retreat was born. I threw together a trip page, put the word out, and by September it was fully enrolled.
I was creating the school of my dreams.
I’VE WANTED TO START A SCHOOL ever since college. It’s an ambition that has remained high on my goal list but never come to fruition because I have a commitment problem. It goes like this:
Regular schools are 10-month-a-year commitments!
And if you’re the founder… it’s more like a year-round commitment!
And… I love travel, adventure, and writing!
And… those take time!
This is why the prospect of a full-time position at even the coolest of schools has always felt like too much of a time-sink. (Same goes for a full-time position… anywhere!)
Settling down to commit to a single physical institution is something I may yet do when my body is broken but my mind remains sharp—but until then, the world is too big, interesting, and deserving of exploration to inhabit just one small corner.
Hence the 4- to 6-week framework for my Unschool Adventures trips: long enough to be life-shaping for the participants, and short enough to leave a feeling of spaciousness in my own life.
But I also love sharing big ideas with teenagers—even lecturing a bit—and travel-heavy programs offer limited time for that. So I’ve periodically stepped away from the travel format to offer more content- and creativity-focused retreats. I did this with four teen leadership programs in 2010-20121, five Writing Retreats, a 10-week Adventure Semester for 23 teens in 2015, and Self-Directed Learning 101, my 12-week online course (and pandemic project) for 25 teens.
Each of these programs gave me an excuse to collect my writing, research, and camp-counselor bag’o’tricks into a single, cohesive experience. Sometimes, the result felt like the best version of what a “school” could be: engaging, immersive, and attended exclusively by those who really wanted to be there (rather than being coerced into attendance by parents or an education system).
Now, at age 40, the Patagonia Retreat felt different—like I was offering something more substantive and original, not just the remixed concepts of my cherished mentors and favorite authors. Happily motivated by the 21 families who had placed non-refundable deposits, I sat down in late 2022 to begin cobbling together a curriculum.
WHAT’S WORTH TEACHING to young adults? The question is endlessly debated. The earliest schools were divinity programs for sons of the elite. The first public schools taught reading, writing, and arithmetic to farmers’ children. The explosion of schooling in the early 1900s turned middle schools and high schools into commonplace institutions for the first time in history, for a variety of reasons: as a replacement for unpalatable child labor, as preparation for a science- and knowledge-based economy, as a form of managerial control and social engineering (Gatto’s hypothesis), and as a kind of benign holding chamber that allowed two parents to work full-time jobs. “What's worth teaching” shifts constantly in response to evolving economies, politics, and communication technology.2
I see valid arguments for teaching standard academics, for teaching the Western canon, for teaching the non-Western canon. I see why the arts matter, why sports matter, why STEM matters. There are a thousand things worth teaching to young people; what we’re really talking about is a matter of prioritization and scarcity. What’s worth teaching to young adults that they can’t easily access elsewhere?
In an earlier post about the Patagonia Retreat, I hinted at my answer: unconventional life paths.
Now, having actually built the curriculum and delivered the workshops, I can be more specific. I believe it’s worth teaching young adults how to lead a life of adventure.
A “life of adventure” is one centered on novelty, uncertainty, and emotion. Travel, entrepreneurship, and the outdoors are classic flavors of adventure, but that’s not where it stops. A life of adventure is any life free from repetitious drudgery, replete with options, and rich with meaning, purpose, and connection.
You cannot lead a life of adventure without reconsidering conventional values, societal mores, and notions of “comfort” and “safety,” which is another reason I’m unlikely to get hired anytime soon as a traditional teacher. I want to teach the stuff that shakes up lives, challenges assumptions, and sometimes worries parents. That’s why I’m self-employed, and why I choose to work with unschoolers. Like John Taylor Gatto, I aspire to be saboteur and provocateur—and such educators cannot count on the goodwill of traditional schools, public or private.
Figuring out how to lead to a life of adventure is tricky. You can pick up bits and pieces here and there, from blogs and books and videos. You must range widely in your studies and meet lots of real people, accumulating a constellation of role models as you chart your own course. It’s a messy, complicated, self-directed process—and one that’s very much worth the trouble.
So, adventure it is. That’s what I’m qualified to teach, and what I think is worth teaching. And teaching it in a month-long, immersive retreat (in Patagonia, nonetheless) suits me well.
Now—what was the actual content?
ELEVEN WORKSHOPS, THREE HOURS EACH: that’s the time I gave myself to teach “lifestyle design,” by which I really meant, “how to lead a life of adventure.”
Each workshop combined slide presentations, videos, discussions, individual and small group activities, and games. I promised the group that I would lecture for no more than one total hour of any three-hour workshop (a promise I broke only once, with advance warning). Here’s a summary of what we covered:
Defining the conventional path. What are the assumptions behind the standard American lifestyle? What are the best criticisms of this path, and what are its best defenses? What’s the point of it all? Here I also introduced the library of 15 books (plus long articles) that I brought for participants to browse throughout the retreat.
Attention and distraction. Seeing “undivided attention” as an economic asset, spiritual wealth, and a form of love. Attending a “focus gym” with guided meditations, listening to long pieces of music, spoken word, and audio lecture. Watching the first 15 minutes of 2001: A Space Odyssey. Practicing reflective listening and open-ended questions.
Money, purpose, time. Asking “how do you create freedom, and then what do you do with it?” Understanding material abundance, Maslow’s hierarchy, and “first world problems.” Considering what money represents, common monetary fallacies, and what can be learned from the FIRE movement (e.g., the power of compounding interest). Beyond money, the vital importance of purpose and time wealth. “Dirtbag rich” and examples of those living with the ultimate trifecta of high hourly pay, high purpose, and high time-flexibility.
Goals. The value of classic goal-setting: dream it, write it, do it. Starting a “100 goals” list. Contrast to “stumble-upon” goals: following intuition, opportunities, and sense of meaning (with examples of journalist Bill Cunningham and my own journey into partner dance). Playing “Yes, and!”
$50/hour + need-finding. How to go from minimum wage to $50+/hour? Matching your unique background with an underserved audience who also has an ability to pay. Exploratory interviewing (“need-finding”) as a way to discover a “market.” Going into El Chaltén to interview locals and tourists about their unfulfilled needs.
Personality. Introduction to Myers-Briggs, Enneagram, and the Big Five (my favorite). Analyzing your Big Five results and how to interpret personality traits. Highlighting strengths instead of fixing weaknesses. Moral foundations as a form of personality (Jon Haidt TED Talk). What Couchsurfing teaches about Openness to Experience and being a good guest. Body language for meeting strangers.
Happiness, movement, connection. Understanding the research behind happiness and mental health. Learning from people who prioritize nature, movement, and friendship (like long-distance hikers, climbers, and dancers). Connections and solitudes. Playing Hot Seat.
College, housing, motivation. Alternative ways to get into college + alternatives to going to college. Alternative forms of housing. Dreaming up your own housing cooperative. Motivation without a boss/teacher. “Hell yes” productivity. Eliminating distractions. Pomodoro technique. What we can learn from Kickstarter and Stickk.com. What Would Odysseus Do?
Global privilege. Taking the Factfulness quiz. Understanding global development and the elephant curve. Power Shuffle to reveal local vs. global privilege. How to actually help, not just feel good about yourself. Checking your comfort addiction. The virtues of actively inviting discomfort into life.
Independent travel. Defining conventional travel. Independent travel planning tools (beginner, intermediate, advanced). Group travel research challenge. Nightmare situations. Vagabonding principles. Analyzing our personal spending habits here in El Chaltén. Low-Cost Good Times vs. Low-Cost Sad Times.
Mortality + hope for the future. Submitting retreat feedback + auctioning off the books. How to become okay with dying? Midnight Gospel final episode. Write your own eulogy. Maintaining hope and security, even with very little. If we met again in a year, one thing you might have accomplished / one way you might have changed? Writing gratitude postcards.
We also heard from many guest speakers who I found through local connections, Couchsurfing, dancing tango, and fliers I posted advertising “Free Dinner for Dirtbags” in a coffee shop and climbing gym. They included:
Juliana (a Brazilian poet, PhD student, and musician)
Jenni (an El Chaltén artist and clothing shop owner)
Frank (an American therapist, Army reservist, and hiking enthusiast)
Anouk (a Dutch doctor and Salsa dance school owner)
Matheu (a Brazilian dirtbag climber)
Dana (a French lawyer who moved to El Chaltén to play folklore music)
Jose (an Argentinian living her dream of fully supporting herself with her artwork)
The teens took regular Spanish classes, which helped them navigate day-to-day interactions and three language exchanges with local teens. They took partner dance workshops that dove into consent, communication, and comfort zones. They also cooked dinners, did the dishes, and collectively managed the hostel: adventures in themselves.
In their free time, many of the participants took advantage of El Chaltén’s extensive trail network; some hiked all the way to the foot of Mount Fitz Roy. And when the retreat ended, they all flew home independently (i.e., together but without a staff member) or stuck around Buenos Aires to do their own thing.
Each of these activities—Spanish, partner dance, communal living, free time in El Chaltén, and independent travel after the program—nicely reinforced the lessons I delivered in my workshops. The guest speakers offered different representations of a life of adventure. No one-man show here.
The Patagonia Retreat was a success. I got to run the school of my dreams!
And I’ll never do it again.
THE BEST ADVENTURES are momentary confluences of people, motivation, and opportunity. To attempt to replicate one exactly is to court disappointment. Better to live it fully and let it go.
The Patagonia Retreat was an adventure for me, my co-leaders, and the teenage participants. In all likelihood, this is the only time that my talented co-leaders will be available for a full month. But even if they were available, I suspect that they wouldn’t do it again—because like me, they saw this retreat as a special opportunity to develop their respective curricula. I harnessed their momentary enthusiasm, just as I harnessed my own. Now, the moment is gone. We move on, happily.
I recognize that institutions matter, and repeated practice matters. The two summer camps that shaped me—Deer Crossing Camp and Not Back to School Camp—were both long-running affairs. I undoubtedly benefited from the fact that each operated for more than a decade before I got involved.
I could attempt to institutionalize and replicate the Patagonia Retreat in order to offer this experience to more teens. I could do it a little better each year, keep hiring new staff, and create a long-running program on which families can count.
But I have so much more to learn! I don’t feel afraid of the challenge of settling down to start a school, but I do think I need (and want) some more time in the big wide world before I can confidently say, “Now I have something substantial to teach, year after year, in a full-time capacity.”
Just because you’re over 40 doesn’t mean you don’t have something valuable to teach. Just because you’re over 40 doesn’t mean you do. Arbitrary age deadlines are just that: arbitrary. Experience matters most. John Taylor Gatto expressed this idea vehemently in his writings, which is why I take his “age 40 rule” with a grain of salt—and why I feel no rush to institutionalize myself as an educator.
For 15 years I’ve delighted in running one-off teen travel programs, each its own little experiment. The only one I’ve repeated is the Writing Retreat, and even that I quickly handed off to a friend in order to create more space in my life for novelty, uncertainty, and emotion.
I’m very excited for this new curriculum I’ve developed and the associated writing project. I have all sorts of ideas for what comes next. Why not linger in the scheming, playing, and prototyping phase a while longer? It’s a beautiful place to be.
Another experiment complete. Now, back to gathering experience.
[Browse more photos from the Patagonia Retreat.]
My 2010-2012 teen leadership retreats were heavily influenced by Deer Crossing Camp’s Leader in Training program.
For more thoughts on the purpose of school, see my 2020 book, Why Are You Still Sending Your Kids to School?
Sounds like such an epic retreat! Everyone who participated was so lucky :)
love you, bro.