Adventures

Since age 20, I’ve organized my life around the pursuit of adventure. (Thanks, Jim.)

2002, Desolation Wilderness

As I wrote in The Way of Adventure:

Adventure isn’t always about climbing mountains or traveling the world. At its core, adventure is about intentionally putting yourself into uncomfortable situations that lead to growth.

All the adventures

For all my big adventures in one handy list, check out my adventure log.

Trip reports

These blog posts share the detailed stories of some of my favorite adventures:

2007, Argentina

A few memories

Running away to South America for 3 months—more or less my quarter-life crisis. Surfing and hiking in Peru, Carnaval in Bolivia, searching for killer whales on the Valdez Peninsula with Matt and Patrick, biking around Bariloche, falling in love with Buenos Aires.

Starting Unschool Adventures and leading trips in Argentina, New Zealand, Peru, Chile, Nepal, Australia, Oregon, North Carolina, and Colorado: more than 100 weeks of my life.

All the backpacking trips in the California High Sierra. Bathing in mountain lakes, sleeping under the Milky Way, forever rediscovering the unique ecstasy of silent granite cathedrals.

Working harder than ever in my life at Deer Crossing Camp. Serving as instructor, assistant director, cook, and interim director. So many Desolation Wilderness trips. LIT Quest and the Tahoe ascent in 2004. Almost getting fired my first week.

The tree-climbing expedition in northern Guatemala with Jim, Julie, and Vince. Waking up in a tent in the high canopy, watching howler monkeys swing past.

Starting a thru-hike of the Pacific Crest Trail, my first big adventure after college. The stark beauty of California’s desert hills. Quitting after two weeks and dealing with the feeling of failure.

Couchsurfing in New Zealand, India, Peru, Europe, and the United States. Hosting Couchsurfers at my cabin in South Lake Tahoe. Here’s my profile.

Writing three books. Having the first one magically picked up by a publisher from a direct email. Independently publishing and financing the other two.

Starting a podcast as an excuse to interview some of my favorite thinkers in education.

Hiking the Camino Primitivo in northern Spain. Discovering a magically welcoming community of fellow walkers.

Short-term international living experiments with friends: Amsterdam, Xela, Medellin, Barcelona, Wanaka.

Hitchhiking across New Zealand’s South Island, over and over again. Never failing to get where I needed to go.

Organizing and teaching a class to other undergraduates at UC Berkeley, at age 21, about alternative education theory. Helping revive Democratic Education at Cal (DeCal) with Nate and others.

Backpacking around Western Europe for 5 weeks at age 19 with Mehar, Bryan, Sam, and Dave. Tasting the freedom of international hostel-hopping.

Trail running epic distances. 32 miles on the John Muir Trail & 27 miles on the Seven Summits with Hannah. 34 miles on the Tahoe Rim Trail. Those long solo runs on the Kepler, Routeburn, and Abel Tasman tracks in New Zealand.

Snowboarding in British Columbia during college breaks with Bryan. Spending an entire winter getting paid to snowboard at Heavenly Ski Resort. Pure bliss at Termas de Chillán.

Spending at a month in Chile at age 14 with a host family. Total immersion Spanish. “Varvala”.

Changing my major from astrophysics (impressive / socially validated / vaguely employable) to alternative education (fringe / hippie / no clear career path) half-way through college. Designing my studies from the ground up, taking full ownership. Writing the crappy 40-page senior thesis paper.

The 10-day Tibetan Buddhism retreat that actually weakened my feelings for Buddhism. Meeting another international trip leader, sneaking onto the roof to talk with her for hours each night, falling for her, getting my heart broken.

Spending an unplanned night in the north rim of the Grand Canyon in December, wearing only canyoneering gear. Good times, Bailey.

Learning to dance Argentine tango beginning with the very first Unschool Adventures trip. Classes in dark, rainy Portland. Running the U.A. tango trip and NBTSC tango project. The private lessons with Alejandro and Zoe. Finally feeling confident in milongas.

Dancing fusion. The first awkward, wonderful festival in the High Sierra. Micro in Seattle. Vail Pass with Unschool Adventures. The Spain Recess. The Green River raft-recess.

Taking part in a German startup competition, in which I helped a group of students to create a concept for a new business. This was mostly a ploy to get myself into Germany during the pandemic, but as a team, we ended up winning the “Social Impact” award and a €2000 prize! Go figure.