The Subtle Art of Provoking Teenagers

on devising a new online community

At the end of the Unschool Adventures Berlin trip in October, I took a long trail run to decompress from the stressful final 12 hours, during which three teens began spontaneously vomiting just before their return flight to New York.

Relieved that the vomiting ceased, the flight departed, and the trip stayed within budget, I allowed myself to begin daydreaming "what comes next?" while bouncing along the soft brown humus trails of the Grunewald.

Unlike in my twenties or early thirties, when I felt the need to offer one program after another to stay financially afloat, I now felt a sense of lightness thanks to my long savings runway and low monthly expenses. It was a moment where I could genuinely ask: "What kind of work do I want? What am I good at? What's worth doing at all?"

One answer clearly surfaced: I should coach self-directed teenagers to take bigger, bolder, and more calculated risks in their lives. To go forth and explore rather than stay home and play it safe. To put away the phone or computer for a while—or at least, to put them to more interesting use. To make the most of their precious freedoms.

I’ve long admired those who do this. John Taylor Gatto embodied this spirit when he sent his middle school students into New York City to survey swimming pools, interview business owners, and lobby politicians. When students at a democratic free school spontaneously decide to build something ridiculous like a trebuchet, or a teen unschooler attempts to learn a new programming language in a single weekend, they too embody this spirit.

All my Unschool Adventures trips have attempted something similar. The Berlin trip, for example, was about voyaging into a big foreign city to discover its mysteries and delights, every day for a full month. The two summer camps to which I've dedicated years of my life (Deer Crossing and Not Back to School Camp) each nurture this ethic in their own, powerful ways.

What if—I asked myself while dodging roots and branches—I could remove the financial and geographic barriers to participating in camp and travel programs, and offer a highly distilled version of the “do big adventures now” ethic? What if I created an online community that focused exclusively on nurturing this spirit—one that supported adventure-hungry young people, wherever they may live?

I'm skeptical of most online communities. Real life is where it's at. But doing something online does permit access to a much larger applicant pool, which means that one can bring together a group of extremely well-matched individuals. What if—my self-interrogation continued—I only recruited teens ready to radically push their boundaries? Those thirsty to be provoked and incited? Those for whom the risk of excess safety now outweighs the risk of trying and failing?

Now that would be an online community I could get behind.

“Coaching teenagers to push themselves is what you’re good at.” (I believe I actually spoke these words out loud to myself on the run.) “What if you reconsidered your skepticism? What if you gave an online community a shot?”

Practically speaking, I envisioned a lightweight commitment, meeting just once a week. I envisioned a community focused exclusively on doing, one in which everyone had skin in the game. And I envisioned a culture in which we both wholeheartedly support and provocatively egg each other on.

Did such a community already exist? My friend

Chris Balme

created something similar called Argonaut for middle-schoolers. But what about a community just for older teens, especially the unschooley types who already think differently and possess serious time-wealth? Nothing existed of which I was aware.

In the days following the run, I compiled a list of 81 adventure challenges for young people. I posted it on Facebook, and it struck a positive nerve—perhaps the community could revolve around this list? I ran the idea past a handful of teens and then threw it on the backburner while cycling in South America.

Over the past week I whipped together a simple website, created a simple-yet-challenging application process (teenager: go do a new adventure, and then tell me about it!), and chose dates for a March-April-May pilot program, ones that fit with my upcoming travels across six countries. Now I’m throwing this thing out there and seeing what happens.

It’s another entrepreneurial gamble and a two-thirds baked idea, but one leavened by the fact that this is what I’ve been doing for 20 years. If even just a handful of teens show up in the beginning, I think it will be a good time. Interesting, meaningful, different. How else do cool things start?

If you know a teenager who might be interested in the Unschool Adventures Club, please point them in the right direction.

a moment of spontaneous adventure, UA Berlin 2023