Off-Trail Learning is an informational website and podcast for young adults who want to blaze their own trails through life.

Here’s a nice illustrated analogy:

As children, we come to believe that success is a well-beaten path. If you follow the path and do what’s expected of you, then you’ll have a happy life.


Sometimes this is true. Other times we discover that the path is overcrowded or doesn’t actually take us where we want to go.


Luckily there’s another option: going off-trail.


Blazing your own trail is hard. You need to be aware of your surroundings, keep your destination in mind, employ the right tools, and motivate yourself to keep going.

But blazing your own trail means: you can go exactly where you want, at your own pace, with companions you enjoy.


At the end of the day, you feel the pride of arriving somewhere that you chose and having defined your own version of success.

Who’s Behind This?

I’m Blake Boles, the creator of Off-Trail Learning.

I’m 33, based in the mountains of Northern California, and I’ve been self-employed for 7+ years as a writer and program leader for unschooled teenagers through my company Unschool Adventures. I love hiking, running in the mountains, and off-trail backpacking… hence the title.

Most importantly: I believe in the power, genius, and necessity of self-directed learning.

Why I Created Off-Trail Learning

Back in college I was studying physics and astronomy. I thought I wanted to become a high school science teacher. Then, out of the blue, a friend handed me a book by the famous schoolteacher John Taylor Gatto. Gatto had taught for 30 years in New York City, won a bunch of awards, and then quit because he “no longer wanted to make a living hurting kids.”

I was completely captivated.

Soon I found myself—someone raised in suburban public schools—diving deeply into the world of alternative education. I discovered unschooling. Sudbury. Summerhill. North Star. Ultimately I ended up designing my own college major to study this stuff full-time.

When I graduated I knew I wanted to contribute to the world of alternative education, but I wasn’t sure how. I became an outdoor science educator for a few years. I worked at Not Back to School Camp (for teenage unschoolers) and Deer Crossing Camp (my childhood wilderness summer camp). I ran away to South America and wrote my first book (College Without High School), which helped me become a public speaker on the topics of unschooling, college, and self-directed learning. Soon thereafter I started my own travel/education company for teens, Unschool Adventures, and wrote two more books (Better Than College and The Art of Self-Directed Learning).

Blake with the Unschool Adventures Nepal 2014 group
Blake (bearded) with the Unschool Adventures Nepal 2014 group

Life was good. I had designed a life and career around what I valued most: promoting self-directed learning, working with teenagers, traveling internationally, and spending lots of time outdoors. But in 2015, I found myself wanting to do something big and reach more young people than ever before—especially those who were still in school. What could I offer?

In my years working with self-directed young people, I’d noticed a few things:

  • Inspiration: Taking an alternative path through one’s education and career can be difficult and anxiety-provoking. Self-directed young people need positive examples and moral support to inspire their continued journey, especially from those who have walked as a similar path.
  • Community: Self-directed learning is difficult when you feel isolated. Teenagers especially need lots of chances to connect with each other, face-to-face. If you have a supportive community, you’re more likely to choose (and stick with) self-directed learning.
  • Resources: There are lots of great resources for self-directed teenagers and college-aged people out there, but there’s no single website that contains them.

That’s why I started Off-Trail Learning: to offer a single website where young people can find the inspiration, community, and resources they need to choose the self-directed path.

Creating a 100% free website and podcast that anyone, anywhere in the world can access felt like a meaningful way to “do something big” and further spread the message of self-directed learning. (If you respect this approach, please consider supporting the site directly.)

That’s why Off-Trail Learning exists. You can learn more on the FAQ. Thanks for reading.