What if It All Falls Apart?

I just launched two big new Unschool Adventures trip: a 6-week adventure in Spain for teens and a 2-week hiking trip in Spain for parents.

I put a lot of time, money, and research into these trips, and I’m super excited for them to happen.

I also know that, for any number of reasons, they might not happen:

  • The itineraries I chose don’t match what prospective applicants actually want
  • The price point is wrong for my demographic
  • My desire to fill trips early (6-8 months ahead of time) is unreasonable
  • Other excellent programs draw away prospective applicants
  • I don’t spread the world about the trips well enough
  • Some unforeseen world event makes travel to Spain unappealing
  • and on, and on…

This is the nature of entrepreneurial ventures, and especially very small operations like Unschool Adventures. Sometimes they just don’t happen.

What do I do if these trips don’t happen? Financially, these trips represent a significant portion of my potential income for the year. I’ve got savings to fall back on, though I prefer not to. But more importantly, how would the failure to fill these trips affect my sense of purpose, contribution, and accomplishment? What else would I do with my time to feel like I’m still “moving forward” in life?

When these nagging doubts creep up on me, I take out my journal and challenge myself to write down a large number of alternative life paths and scenarios. I force myself to get out of the “one right answer” mindset (i.e., run the Spain trips) and generate “second right answers” that would make me feel like I’m still making the most of my life.

In that spirit, here’s what I wrote this morning:

(Excuse the redacted bubble, it’s something I’m not at liberty to share.)

Each of these paths would feel like a good—or at least interesting—use of my time. Some would earn money, most would not. I’d really prefer to run the Spain trips. But lists like these help me feel reassured that, if it all fell apart, my world would not in fact collapse.

Who I Want to Be at Age 35

This September I turn thirty-five. Most age landmarks are arbitrary, but 35 is where I personally separate “young” adults from “adult” adults. So I’m taking this upcoming birthday as an opportunity for personal reflection as I move into the adult-adult, no-more-benefit-of-the-doubt, no-excuse-not-to-have-your-shit-together stage of life.

Here’s who I want to be at age 35:

a truth-teller. I want to pursue truth wherever it leads. If one of my cherished ideas (such as the efficacy of unschooling or self-directed learning) proves itself bankrupt, I’ll walk away from it. If I’m curious about something that’s politically distasteful to my community, I won’t stop looking into it.

a mentor and teacher for young adults. Nothing gives me more pleasure then helping a young adult (typically ages 13-21) to develop their skills and ideas. To see a new part of the world. To discover a new way of enjoying life. To take another step along their path—or make a radical course-correction. This will be my fifteenth year of working with young adults, and I only want more of it.

a skill-builder. I want to keep doing hard things that demand real skills and offer real chances of failure. Speaking Spanish. Partner dancing. Running long trails. Backpacking deep in the mountains. Writing and speaking for public audiences. Running my own business. To paraphrase Nietzsche, I want to to feel the happiness of my power increasing each year.

radiantly healthy. I want to avoid the gradual descent into frailty that seems to start around now. I want to be stronger, more flexible, less prone to injury and sickness than I was at age 34. This connects to who I want to be at age 70, which is “that grandpa still doing crazy backpacking trips” and “that old dude totally cutting up the dance floor.”

making new friends. As I continue meeting new people, I want to turn some of them into long-lasting friendships. Around my age, many people seem to simply stop making new friends; they accumulate acquaintances and “contacts,” but not deeper connections like they did in college or their mid-twenties. I’m going to continue investing energy in making friends without ulterior motives (i.e. romantic or business).

economically beholden to no one. I decided early on that I’d rather be poor and free than rich and trapped, and I bring that intention into my thirty-fifth year. I’m debt-free. I report to myself. I get to choose my clients, choose my obligations, and choose which sh*t sandwiches I eat. I make much less than my demographic peer group, but I feel secure, and I own the time of my life.

willing to reevaluate my identity. As I wrote this post, it was interesting to see one thing that didn’t make the list: travel. Because I’ve built travel into my personal identity, sometimes it’s something I feel like I need to keep doing—otherwise, who am I? But then I stop and think: okay, if I don’t travel, I won’t cease to exist. No one will disown me. And I might even be able to do some really cool stuff that travel prohibits. It’s truth-telling to myself, I suppose. At age 35 I don’t want to be afraid to kill my sacred cows, discard what’s no longer serving me, and reinvent myself.

My First Online Course: The Way of Adventure

Today I’m proud to announce The Way of Adventure, my first online course. It’s an advanced leadership course for ages 13-23, but you can participate at any age. The best part: it’s 100% free.

What’s the message?

One the big reasons I created this course was to better explain my idea of “adventure.” I consider myself an adventurer, but I’m not always off on dangerous outdoor trips or exploring far-flung corners of the globe like other adventurers I know. I prefer a more commonplace and accessible conception of adventure, which I started to define 8 years ago in College Without High School:

An adventure, specifically defined, is any challenge that requires a lot of learning in a small amount of time.

The passage continues: “Traveling cross-country to teach rock climbing at a summer camp is an adventure. Crafting an online marketing plan for your friend’s small business is an adventure. Spending three months on an organic farm in Italy to learn permaculture and the Italian language is an adventure. Walking into a physics professor’s office to get book recommendations, working nights as a veterinary assistant and volunteering at a disaster relief site are all adventures. And going to college, too, is an adventure.”

With this new course I share my updated definition:

At its core, adventure is about intentionally putting yourself into uncomfortable situations that lead to growth.

Continued: “It’s about designing a life instead of accepting the one you’re handed. It’s about living in such a way that, whether you die next week or at age 90, you will not regret your choices. You can still have safety, comfort, and approval with a life of adventure. Same with degrees, jobs, cars, houses, and spouses. But they’re byproducts of a life well-lived—not its ultimate purpose.”

I continue promoting “adventure” because it’s a universally popular idea with young people and an easy gateway to the ideas of self-directed learning and taking control of one’s education. I also think adventure is a good thing on its own, separate from any notions about education; I like pretty much every adventurous person I meet, regardless of their beliefs about the school system. These people are typically optimistic, courageous, conscientious, and forward-looking. It felt right to design my first online course around “adventure” rather than my time-worn banners of self-directed learning and unschooling. Continue Reading

2016 in Review

Welcome to my annual year in review! I’ve got lots of photos and stories to share with you from a very adventurous 2016.

This year I’m also doing something new: Instead of just recounting the past 12 months, I’m also doing a forward-looking review. I’m going to tell you now what I hope to have accomplished by the end of 2017.

The question I’m asking myself, as Chris Guillebeau puts it: “This time next year, what 3-5 things will have made the year amazing?”

By December 2017, I hope to tell you that I…

  • ran two impactful programs for self-directed young people that earned glowing feedback: the 12-week Argentina Semester and 7-week Southeast Asia trip.
  • gave presentations in England and Europe as part of a self-organized speaking tour meant to spread the ideas behind self-directed learning.
  • dedicated serious time to dance—tango and blues fusion—through festivals, private lessons, and social dancing.
  • built, tested, and launched my first online course.
  • spent at 30+ days hiking or backpacking.

I see this as a combination of new year’s resolutions, staying true to my goals, and fortune-telling. I’m not discounting the possibility or importance of serendipitous events; I’m just trying to go into 2017 with some clear intentions for how I’ll measure my success.

Alright—now back to 2016! I’ve divided the year into five parts:

  1. Guatemala
  2. New Zealand
  3. Argentina
  4. California
  5. On The Road

Part 1: Guatemala


On New Year’s day I woke in Xela, Guatemala, where I spent January escaping the winter, improving my Spanish, and reflecting on my nomadic lifestyle. I arrived on December 31st from Oaxaca (Southern Mexico) via a series of buses, taxis, and bicycle rickshaws. Traveling solo with a lingering lower back injury, I wasn’t able to walk very far, so I spent a lot of time working from my sweet top-floor apartment overlooking Xela (a.k.a. Quetzaltenango) which I rented for $550/month.

Xela, Guatemala

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Only beautiful things lead us out to join the world beyond our heads.

Matthew Crawford

The World Beyond Your Head is Matthew Crawford’s second book, following Shop Class as Soulcraft—one of my all-time favorites.

I enjoyed this book, but cannot say that I recommend The World Beyond Your Head to the casual reader. It’s much denser, more philosophical, and less accessible than Shop Class. But if you have a soft spot for sometimes-intractable political philosophy and social commentary with brief shining moments of illuminating truth (as I do), it may be worth your time.

What I took away was a powerful critique of the Enlightenment-driven concept of the autonomous individual which lies at the base of how I understand (and promote) unschooling and self-directed learning. Yet at the same time, Crawford reinforces the value of experiential education.

Here are my favorite quotes, all taken from the U.S. paperback version. All emphases are original; all typos are mine.

On silence and stimulation:

The benefits of silence [such as in an airport waiting area] are off the books. They are not measured directly by an econometric instrument such as gross domestic product, yet the availability of silence surely contributes to creativity and innovation. They do not show up explicitly in social statistics such as level of educational achievement, yet one consumes a great deal of silence in the course of becoming educated. (p. 11)

The media have become masters at packaging stimuli in ways that our brains find irresistible, just as food engineers have become experts in creating “hyperpalatable” foods by manipulating levels of sugar, fat, and salt. Distractability might be regarded as the mental equivalent of obesity. . . When we inhabit a highly engineer environment, the natural world begins to seem bland and tasteless, like broccoli compared with Cheetos. Stimulation begets a need for more stimulation; without it one feels antsy, unsettled. Hungry, almost. (pp. 16-17) Continue Reading