Career Trajectory Update

September 7, 2017

I just finished working my 12th summer of Not Back to School Camp: an annual milestone where I reflect deeply, talk with long-time friends, and choose new directions for my life and career.

After camp last year I determined that running Unschool Adventures trips doesn’t pair well with my longer-term goal of being able to work from anywhere, ideally with a family in tow.

I still love running big trips for self-directed teens, and I plan to continue offering one trip a year for a long time. But as I turn 35 I’m feeling ready to turn Unschool Adventures into a side gig and take a bold new direction with my primary career path.

Here’s a birds-eye view of this new trajectory.

New Focus: the Parenting of Self-Directed Teens

Teenagers are my jam. Ever since college, they’re the age group I’ve felt most compelled to serve. Now I have over a decade of experience working with teens through Unschool Adventures and summer camps; doing one-on-one coaching with teens; and speaking for teen groups.

My approach has been to work with teens directly, with minimal parent involvement. This began at Deer Crossing Camp, where I witnessed the transformational power of a 4-week teen leadership program away from home. Then I read Grace Llewellyn’s Teenage Liberation Handbook, the only education book I’d seen that directly addressed an audience of young people; I followed suit by writing College Without High School and Better Than College directly for teens. In Unschool Adventures trips, parents play almost no role beyond paperwork and payments: it’s really just the trip leaders and teens off galavanting around the world, sending an “I’m still alive!” email home every now and then.

I believe this has been a valuable and important approach to take: it makes young people feel like I take them seriously, it breeds mutual respect, and it encourages teens to act like the adults they will soon become. But I think I need to expand beyond this approach.

If I’m more honest and less self-congratulatory, the parents of teens actually do play a huge role in everything I’ve been doing. It’s overwhelmingly the parents (mostly the moms) who find my books and programs and share them with their teens. They provide all sorts of non-financial support. The fantasy that I hold of the self-empowered teenager who’s essentially a fully functioning adult living at home seems to be just that: a fantasy.

The teens with whom I work have incredibly involved parents. Not involved in the controlling, helicopter-parenting way, but involved in the deep-connection, deep-trust kind of way. They know their kids really well. From they outside they appear hands-off, but this approach is informed instead of neglectful. The balance they strike is really quite incredible. While the nature half of the nature/nurture debate seems to play a larger role  than we imagine, it’s clear to me that the awesome teens with whom I work do not arrive in utero. Parents and parenting matter—big time.

Logical conclusion: If I want to help more teens, I should help more parents.

I want to learn more about the parenting practices that undergird the lives of the badass teens whom I serve. I’m not looking to accumulate parenting “tricks”—I’m interested in nuanced styles, beliefs, techniques, and philosophies. If I can identify these and distill them into something useful and novel, then perhaps I can inspire more parents to raise their teens in an environment saturated with more freedom, respect, consent, trust, and personal responsibility than they’d otherwise have.

This new focus could expand my reach beyond the narrow subset of families I’ve mostly served thus far: those with the motivation and ability to unschool their kids. Widening the circle of families I work with feels right to me on many levels.

(If you find yourself saying, “What the hell are you thinking, Blake, you don’t have any kids! Why would anyone listen to you about parenting?”—I have a few responses. First of all, many parents already do listen to me. Second of all, I have tons of face-time experience with teens, which isn’t the same as having a child, but it still counts for something. Thirdly, there may be a benefit to giving parenting advice without the bias of having children oneself: it lends a certain degree of objectivity.)

Reawakening the Writer-Researcher-Academic

My last book, The Art of Self-Directed Learning, was released three years ago. Since then I’ve haven’t felt that I have another book in me, but my desire to research and write has remained.

Though my travel- and adventure-heavy lifestyle appears to be more about “doing” than “thinking,” my academic side has never really died. I’m constantly reading. For years I’ve shared my favorite education-related articles each month through my email newsletter. I receive a constant drip of emails from readers of my books, which I suspect have done more good than all my in-person work.

This is all to say: I’m looking for an excuse to dive back into reading, researching, and synthesizing ideas. I’m excited to go spelunking for source material, vet studies, and strike that magical balance between scientific validation and anecdotal accessibility. I want that challenge in my life again.

Not Another Book

“So why not write another book, Blake?” Good question, Blake. That seems like a logical progression from everything I’ve said above.

Here are my problems with that idea.

Money: I’ve learned enough about the publishing industry to know that only blockbuster books make money today, and the author needs to bring a huge platform (i.e., social media followers, blog readers) to get taken seriously by agents and publishers. I don’t have a blockbuster idea or a huge following right now, so I don’t think it’s a good bet for me as a career move. My three books have served (and continue to serve) me well as ways to share my philosophy and attract people to my in-person programs (which actually pay my bills). On my current scale, a book will not be a significant money-maker, and there are less time-intensive ways to attract new readers (like writing articles).

Engagement: We are increasingly accustomed to consuming lots of different types of media: videos, podcasts, games and interactive websites, short- and long-form articles. I’m not going to make a pessimistic comment here in the vein of “people don’t read books anymore,” but I do believe that my message can benefit from more media diversity. To maximize engagement, I think whatever I create should be multi-modal, not just written.

Sameness: Essentially, I’ve done the book thing. It doesn’t feel new, fresh, and exciting to me. Maybe that feeling will return down the line.

Maybe an Online Course

So what can I create, if not a book, to share what I learn? The answer, I think, is some sort of online course, workshop, game, or other computer-based experience for parents.

Here’s what I like about this idea:

  • I can reach a worldwide audience.
  • I can create something highly engaging and multi-modal (combining video, audio, and written material).
  • I charge more than I do for a book while remaining financially accessible to most families.
  • The need for ongoing promotion would give me a reason to continue speaking for parent groups, which I already do and enjoy.

I also have very mixed feelings about the allure of creating an online courses. Essentially:

  • Face-to-face experiences are always more powerful than online ones.
  • I’m not a consumer of such courses, so why would I think I can create a good one?
  • More people like the idea of profiting from an online course (drawn by the promise of location-independent, “easy money”) than actually taking a course themselves.

This is why I say “maybe.” I don’t want to sell snake oil to myself. I don’t want to get carried away creating something that no one actually wants to buy. So I’m leaving the format open for now.

Steps I’m Taking

You can see this blog post going from high-clairty to low-clarity, fairly rapidly. I don’t have a concrete plan, but I’ve got to start somewhere. Here’s what I’m done so far.

Reading a bunch of books related to parenting teens. I’m curious about the current state of parenting advice for teens—certainly slanted toward my preexisting biases—so I surveyed some parents on Facebook and spent about $150 to indulge my research whims.

Some of my new books, strewn on Grace Llewellyn’s floor

Outlining a potential Fall 2018 US/Canada road trip to visit parents and schools. I have a great network of parent contacts and alternative schools / self-directed learning centers that I’d like to visit or re-visit. I envision a combined research trip and speaking tour, where I go around interviewing parents and educators while funding the trip with speaking gigs.

Experimenting with video. I’ve created a lot of written and audio content but little video. I find it daunting. So I’m recruiting a friend to help me experiment with creating highly engaging video content.

Hiring my own boss. For a project of this size, I recognize the need for someone to manage it—and more importantly, manage me—as I do my research and create content. I’ve lined up another friend to serve in this role.

Giving myself the time and money needed to really dive in. Perhaps most importantly, I’m setting up my 2018 calendar to allow for many months of deep-diving into this new trajectory, and I’m giving myself permission to spend some of my savings on this (which I’ll hopefully later call “investment” rather than “spending”).

Want to Follow My Journey?

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As always, thanks for reading and caring.




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