Reflections on Trailblazer

Trailblazer Gathering—the new event that I’ve spent half a year planning—just ended. Overall it was a great success, and I plan to do it again next year. Below are my further reflections.

1) 18- to 22-year-old self-directed learners are diverse and awesome.

For me, the best part of Trailblazer was meeting young adults from across North America who are boldly carving their own educational paths. Many of them I previously knew from NBTSC and Unschool Adventures, but just as many came from outside the “unschooling mafia” (as we started calling it), heralding from traditional schools or homeschooling backgrounds. A few had recently made the decision to leave college, and Trailblazer was their first stop.

As I discovered years ago when I first started working more closely with teen unschoolers, young adult self-directed learners are kind, curious, passionate, skilled, and genuine human beings. They’re a demographic that I’m proud to serve, and they’re ultimately the reason I’d like to run Trailblazer again.

2) I tend toward over-scheduling.

As the organizer of a big, new event, I expected to make (and did make) lots of little mistakes. One that quickly became obvious was how I over-scheduled: running activities from 8am to midnight, packing too many speakers into the evening “focus” sessions, and running workshop slots back-to-back with little transition time. While every activity at Trailblazer was fully optional and everyone had the freedom to strike out and do their own thing, most people followed the schedule and felt like the days were endless.

To remedy this, participants and leaders suggested that I add more purposefully unstructured time for drawn-out discussions, spontaneous adventures, and participant-generated activities. I agreed, and I plan to make those changes next year. I’m now more aware of my tendency toward over-scheduling, and I’ll watch out for that in future programs.

Photo: Sam C.

3) You can’t please everyone.

A tiny minority of participants had gripes with Trailblazer, and one person was so inflamed that she decided to leave early. This was a first for me—no one had every voluntarily quit one of my programs. I went to great lengths to listen to and accommodate that particular person, but in the end I realized that she brought an entire host of very specific expectations and assumptions about how Trailblazer would be run that went far beyond anything I advertised on the website, so she ultimately could not be accommodated.

This experience made me think hard about how much attention I should give, as an event organizer, to a highly dissatisfied vocal minority. I highly value constructive feedback (as anyone who’s done an Unschool Adventures program with me knows), but if one person’s complaints occupy 50% of my attention, then I’m not serving the rest of the participants—those who are happy and excited to be there—as well as I could.

Photo: author

4) A big, strong leadership team is an incredible thing.

In the past, my Unschool Adventures programs have involved very small leader groups—one or two others plus me. At Trailblazer, I brought together roughly a dozen leaders to help run the show. It was a glorious thing.

Ingmar led an incredibly popular workshop. Dev took people on multi-hour life-coaching walks. Brenna navigated the River Arts District, Ethan talked about investing, Sean did time-lapse videography, Cameron coached swing dancing, and Hillary taught sexual consent. Autumn and Matt (my “official” staffers) did just about everything under the sun, but most notably, organized a 30-person flash mob in just a few hours. And many others (who I don’t have space to mention here) did so much more.

The leaders made this event something that I could never make it myself. I’m honored to have worked with such an excellent team, and I’m excited that so many of them have already shown interest in returning next year.

Photo: Sean R.

5) I figured out some of my own priorities.

In the first evening “focus” session, I asked the group a question that I adapted from Derek Siver’s blog: How would you grade yourself, if money and status were taken off the table? Would you grade yourself by the number of lives you changed, the number of useful things you produced, or the quality of your relationships? In other words: what are your metrics for finding success in life?

Before asking everyone else this question, I sat down and answered it myself. I came up with three ways in which I grade myself:

  • How many lives I change by showing new educational paths.
  • How often I visit my friends and family.
  • How many transcendent moments in nature I experience.

This was interesting news to me. I hadn’t sat down and really thought this concept before, and I’m glad I did. It helped me to remember my priorities and assess my level of “success” as I move forward through life.

Photo: Sean R.

Look forward to the Trailblazer 2014 information appearing this Fall. Join the Trailblazer mailing list to get an e-mail when it launches.

For more media, you can browse all the Trailblazer photos and watch our flash mob video (warning: explicit lyrics).

Photos taken by: Jake K., Sean R., Sam C., and yours truly.



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