I just cancelled another Unschool Adventures teen trip.
I needed 12 early applicants to move forward with confidence. I received just four.
This isn’t a total surprise. Roughly two-thirds of the programs I’ve offered since 2008 haven’t received sufficient interest to move forward. But because every trip is a unique offering, every cancellation also means watching a whole bunch of planning and marketing efforts evaporate. I also had high hopes for this 4-week, US-based retreat, as similar programs have been popular in the past.
This is a small price to pay to sustain a business that’s allowed me to travel the world alongside fun, good-natured, and non-entitled teenagers, offer any “curriculum” that seems worthwhile, hire my trusted friends as co-leaders, earn decently without monopolizing my life, and create experiences that give young people genuinely high (and rare) levels of freedom, responsibility, and permission to explore.
It’s also given me a satisfying personal elevator pitch: I take teenagers on unconventional international adventures through my own little company. 🫦🔥🚒
All of which makes Unschool Adventures scary to walk away from. But that’s exactly what I think I need to do.
To be clear, I’m not closing the company—I’m just putting it on ice. No trips for a good, long while. And when it returns, it may not look the same.
Thanks to the savings I’ve accumulated by trip-leading (plus speaking, writing, and dirtbag rich thriftiness), I can afford to do this. I also want to live in Europe again, which complicates things when teenagers need to be escorted on group flights from North America, or when I want to obtain a foreign residency permit that says I shouldn’t be working from abroad.
Practicalities aside, I want to take a leap. Starting Unschool Adventures at age 25 felt like a leap, especially as it aligned with my first book and the beginning of my public speaking career. What might a similar leap look and feel like now, at (almost) 44?
Stepping away from a safe and familiar crutch—even one as empowering and non-intrusive as Unschool Adventures—seems essential to answering this question. I want to allow the idea of Unschool Adventures to evolve, rather than continuing to run programs out of habit and familiarity.
Pull the ripcord. Invite the evolution. Create the conditions required for change.
I may seem calm, but this is scary.
The other night, I fell asleep with these words in my brain:
You’re not going to go hungry.
The next morning, on a run, I heard these words:
You’re only free to the extent that you’re not afraid.
I keep chewing on this nugget from Friedrich Nietzsche:
For believe me, the secret for harvesting from existence the greatest fruitfulness and the greatest enjoyment is to live dangerously! Build your cities on the slopes of Vesuvius! Send your ships into uncharted seas! Live at war with your peers and yourselves! Be robbers and conquerors as long as you cannot be rulers and possessors, you seekers of knowledge!
And these words from my former tango teacher (turned Buddhist monk), Alejandro:
What defines us is not our identities—it’s how courageous we are, and how much risk we’re willing to take.
Is the world telling me something? Am I telling myself something? What’s the difference?
I discussed all this with a personal coach who pointed out that Unschool Adventures has provided connection, freedom, and growth to both teenagers (as participants) and myself (as organizer, trip leader, and business owner). By stepping away, I’m entering the “teenager” role: exploring the unknown, leaving a place of safety and familiarity, and moving forward without a clear understanding of what comes next.
I reallllly need to see myself as useful to other people. As soon as I consider pausing Unschool Adventures, my mind rushes in to fill the void with other projects. Some of these projects, like online teaching or going deeper into dance, feel right. Others feel like anxious expressions of the idea that I’m worthless if I’m not constantly creating and running programs—if I’m not employing the skills I’ve built over a lifetime.
Sitting in stillness, dwelling in uncertainty, and not having a compelling response to the question “What are you doing with your life?” leaves me deeply unsettled.
Then I remind myself that I’m not retiring from youth work, alternative education, or travel. I’m just reassessing the particular machine I’ve built for connection, freedom, and growth. My values aren’t changing. I just need to express them differently.
For now, I’ll keep riding my bike northward to British Columbia (aided by Amtrak) before boomeranging back to Portland, stashing the bike with an old friend, and hopping a one-way flight across the pond.
Get involved
To share your thoughts on the evolution of Unschool Adventures, click here:
To learn about my upcoming online offerings (like workshops and connection games), join my new email list:
If you have an idea about how we might collaborate, reach out anytime: blakeboles@gmail.com
😘
—Blake
Can really relate to being in a place of wondering what is next/what is life going to look like going forward. I admire your willingness to embrace risk and uncertainty tu though. It’s something that I’m trying to wrestle with myself as I get older and life no longer is centered around just me, but has consequences on other people too.
Blake! Always an inspiration. Of course we’ll all be following and supporting whatever you do next.
How long will you be in Portland?
Any chance you want to schedule a workshop for PDX teens/young adults while you’re here? I can help make it happen if so. 😊