Workshop Leader Résumé
on teaching "lifestyle design" to young people
FROM: Blake Boles
TO: The 21 participants (age 16-20) of the Unschool Adventures Patagonia Retreat
RE: My qualifications
Soon we’ll meet in southern Argentina, where you’ve agreed to attend four weeks of “lifestyle design” workshops led by me, Blake.
That’s 12 workshops, or 36 hours in total… mucho Blake time.
I’d like to tell you a little about what qualifies me to lead these workshops, and why you might want to pay attention to what I have to say.
I’m doing this because when I was in high school, I hated knowing so little about my teachers. Was my chemistry teacher an actual chemist? Had my English teacher written any books, essays, or poems? Why did they become teachers? Did they really care about their subjects?
I would have loved for these adults to begin their classes by candidly discussing their relationship to their subjects, why they became teachers, and what they really hoped we would gain as students (beyond curricular requirements). I wanted to trust my teachers and understand their motives instead of just experiencing them as authority figures.
So, here’s my introduction. I planned on doing it in Patagonia, but by doing it now, we can hit the ground running. And since this is probably a topic of interest for your parents, and perhaps others, I’m making it public. Vamos.
First, let’s remember what you signed up for. Here’s what it says on the Patagonia Retreat webpage:
As you move into adulthood, you face many choices. In each situation, you can either conform to the default path, or you can actively design a more alternative and individual path. But this is only possible if you are aware of your options and possess the confidence and encouragement to take an unconventional route.
As someone who has fueled his life with self-employment, long-term travel, and frequent adventures for more than 15 years, Blake will guide you through the world of unconventional approaches to work, education, housing, travel, and more.
The first question you might want an answer to: Do I have evidence for these claims? Have I really lived some kind of “unconventional” life?
Here are the facts.
I started Unschool Adventures in 2008 and became fully self-employed in 2010. I fund my life by running my teen trips, selling books on Amazon, and doing occasional workshops. Since finishing college at 22, I’ve been financially independent. I don’t have a trust fund or family money. I don’t take government support (beyond subsidized healthcare and one-time pandemic assistance). I never struck it rich on the stock market, never owned property, and don’t anticipate an inheritance. I have saved enough to stop working for multiple years, should the need arise.
LONG-TERM TRAVEL & UNCONVENTIONAL HOUSING
For virtually all of my adult life, I haven't lived in one place for more than 6 months.1 Previous habitations include rented rooms in shared houses, a mountain cabin, a tent, the back of my car, youth hostels, Airbnb rooms, friends and family (never too long), Couchsurfing, and an unfinished yurt.
Previous temporary homebases include Amsterdam, Ashland, Berkeley, Boulder, Buenos Aires, Crested Butte, Freiburg, Idyllwild, Medellín, Paradise, Paonia, Portland, San Francisco, Santa Cruz, South Lake Tahoe, Wanaka, and Xela.
I’ve backpacked parts of the Pacific Crest Trail, Te Araroa (New Zealand), Camino de Santiago (Spain), and Annapurna Circuit (Nepal). I’ve biked across multiple European countries and US states, trail run 30+ miles, and hiked off-trail for weeks in the High Sierra. I’ve solo traveled across South America, hitchhiked across New Zealand, climbed+slept in trees in Guatemala, road-tripped the Colorado River to understand its politics, taught windsurfing to kids, got paid to snowboard for an entire winter, and smuggled myself into Germany despite a pandemic travel ban. Plus all the Unschool Adventures trips I’ve run—22 and counting. Here’s a log of all my big adventures.
But I also don’t believe all “adventure” must be outdoor- or travel-related. I’ve attempted a 10-day silent meditation retreat, crowdfunded and self-published three books, gone on speaking tour, run a podcast for seven years, learned acroyoga and thrown myself into partner dance without previous experience or friends by my side—each an undeniable adventure.
In college I designed my own Bachelor’s degree in Alternative Education Theory, taught classes to other undergraduates, and lived for years in a strange, delightful, democratically-managed 125-student housing cooperative (officially known as Casa Zimbabwe, lovingly called Krackistan) where I cooked dinners for 100 and eventually managed a $60,000 food budget.
After college I considered graduate school, decided the real world was more appealing, and continued my education by devouring books/articles/podcasts, emailing strangers, attending conferences, and getting certified as a Wilderness First Responder and Emergency Medical Technician. I consider myself self-taught in many fields beyond my formal training (see my interests).
I love my work. I feel like I contribute meaningfully to the world, and I have friends everywhere. I make enough to pay my way and save for a rainy day. I enjoy lots of free time to learn new things, explore the world, move my body, and go on big adventures.
Now, the next question: Am I full of myself?
In response, I say:
Yes, I take pride in my path.
Please don’t assume you should live like me.
We’re all products of our genes and environment. And my environment, I’ve come to realize, was tilted toward “adventure,” for both better and worse.
I don’t think I’m better than anyone. I don’t believe I’m abnormally talented or courageous. And I certainly don’t assume you (or anyone) should follow in my footsteps. But I do believe that my somewhat non-traditional path (and others who have taken similar paths) offer a helpful counterpoint to the prevailing narrative about becoming a Successful Adult, which goes something like this:
Go to college (and probably graduate school) and get a degree in a safe, marketable field
Go straight into full-time work, and don’t take significant time off
Get your own place, start buying nicer products and services, go on fancy vacations, and otherwise match your spending to your income
Prioritize stability, attach yourself to large organizations, don’t take big risks, invest in property
Give up personal hobbies, adventures, and creative pursuits in the pursuit of financial security
Orient life around preparing for a comfortable retirement
Listen: I really don’t judge anyone who takes this path. I have friends who did all of this and have wonderful lives. And having parents on this path may be the only way you afford to join my program! So let’s not be hypocrites, or elitists, or spoiled brats—all paths are valid as long as they don’t trample others. Which is why I also wrote this on the retreat webpage:
This isn’t about knee-jerk rejection of everything “normal”—it’s about considering a multitude of life paths, understanding their implications, and honestly weighing the risks and benefits.
It’s important to note that my life doesn’t currently include long-term partnership, children, or home ownership—all of which give tremendous satisfaction and purpose to many people, and which radically shape the landscape of “lifestyle” possibility. I’ve also been fortunate with my own health and my family members’ health. I’ve experienced no major tragedies. (Luck plays a larger role in our “choices” than we like to admit, especially the victorious ones.)
So, as your workshop leader, I hereby promise to walk the tightrope of (1) being fair to traditional vision of success that prioritizes the safety & security that many of us want & need, while also (2) advocating for an alternative vision:
Success is waking without fear of the day to come.
Success is exhilarating stress, happy exhaustion.
Success is finding yourself by losing yourself.
Success is making someone else’s day better than it otherwise would have been.
Success is contributing to the human project.
Success is being missed if you don’t show up.
Success is feeling spaciousness, having options.
Success is being in control without minding the destination.
Success is doing little that you must, and much because you choose.
A poor person can be more successful than a rich person.
A bad student can be more successful than a star student.
The unemployed can be more successful than the employed.
You may even discover that these different versions of “success” aren’t as different as they first appear—and that embracing an alternative path as a young person may still lead you (or better lead you) to conventional success in later life.
Finally: Why do I care so much about this “lifestyle” stuff?
Why can’t we just hang out in Patagonia—go on some nice hikes, cook some nice meals, dance a little, learn a little Spanish—and call it a win?
The answer: Because I genuinely wish that, when I was 16- to 22-years old, someone had given me direct, no-bullshit advice on these topics.
This is why so many frustrated high school students ask themselves: “When are they going to teach us something real?”
Never in high school or college did I encounter a class entitled Alternative Approaches to Career and Lifestyle, Reconsidering Traditional Definitions of Success, or Adventurous Life 101. God, I wish!
Instead, I cobbled together my knowledge from books, conversations, experiments, and a dozen other sources. It was the rich, slow journey of self-directed learning… and I also wouldn’t have minded a nice, formal introduction to the subject.
“Write the book you want to read” and “Teach the course you want to exist.” That’s good advice, and it’s what I’m attempting. I want to share the best arguments, philosophies, and perspectives that shaped me as a young adult, in an organized and engaging fashion, with those who are willing to hear what I have to say.
If you’ll have me as your teacher,
I’m delighted to have you as my student.◾
I did have multi-year stint in Asheville (North Carolina) for a long-term relationship, but even then, I spent significant time away for work, travel, and adventure.