Education ➡ Adventure

on the origins of this project

Twenty years ago, I stumbled into the world of alternative education by discovering a few great books. This intellectual awakening led me to abandon my path in the sciences, design a major in education, and begin working face-to-face with self-directed teenagers. 

These teens, in turn, inspired me to continue reading, writing, and exploring the topics of motivation, productivity, college admissions, and alternatives to college, resulting in four moderately successful books (5000+ copies sold each), a fun podcast (~100 episodes), and little side-careers in public speaking and private coaching.

From the outside, it might seem like I’m highly invested in the world of education. But truthfully, I’ve always had one foot out the door. 

I’ve never worked full-time in a traditional school, alternative school, or self-directed learning center. I’ve dreamed about starting my own school but haven’t taken serious steps in that direction. I’ve never run more than one or two teen travel programs per year. 

I never became a full-time educator because one thing always felt more important to me: adventure. 

Outdoor adventures. Travel adventures. Entrepreneurial adventures. Writing adventures. Dance adventures. Every time I tasted a new kind of adventure—around age 11, 14, 20, and 25, to name a few milestones—I felt less content to lead a stable, predictable life. 

At the end of my twenties, I told myself that my lust for adventure would surely wane, and I would soon feel content sticking to a single place or single project.  That did not come to pass. Throughout my thirties, my appetite only increased. Now I’m almost 40, and I’m dreaming bigger than ever.

I’m addicted to the novelty and uncertainty of adventures. I love discovering new places (as I did on my European bike trip last autumn) and reconnecting with old favorites (like the Sierra Nevada). I love visiting old friends scattered across the world and making new connections at the same time. 

My Unschool Adventures trips help teenagers see the world and build independence, but I also use these trips to fuel my personal explorations—which explains why I’ve never run the same trip twice, despite how sensible it would be from a business perspective.

Even my educational beliefs, I recently admitted to myself, are heavily fueled by adventure. Why is school such a potentially destructive force in the lives of young people? Because it stifles adventure and promotes boredom, naturally! That was the thesis of my first book—and most of the other ones, too. All paths lead to adventure.

This lust for adventure affects my personal life. Full-time, year-round commitment to any job, place, or person has felt threatening to me, because any such commitment compromises my ability to migrate between the hemispheres, go on long backpacking trips, pop across the country for a few weeks, or immerse myself in a new creative project. While my life is rich with friendships and adventures, it is also noticeably lacking in stable employment, long-term relationships, children, and home ownership.

All of which makes me wonder: Where does this undying allegiance to the concept of “adventure” stem from? What makes it the driving force behind my life (and the lives of many others)? What’s the psychology of adventure? How does it overlap with other lifestyle choices, like minimalism and entrepreneurship? How did the modern concept of adventure evolve, and why is there such a romanticism about it? And what happens, in the long run, to those of us who chronically choose adventure over more traditional goals?

In short, I’m considering a sociological investigation into the world of “adventure,” writ large.  An investigation that shines light onto a popular modern phenomenon—and also, perhaps, my own life and choices.

Maybe this is the start of my next book. Maybe it’s another curiosity I’ll indulge and move on from. Maybe I’m just rationalizing my ongoing travels.

Regardless, the journey will be the reward—and I plan on documenting that journey here.

Stick around.