Back in December 2022, I offered a year of free, one-on-one mentorship for a handful of young people. Following a stringent vetting and appeals process, I ended up with a single mentee: Ben Rehrman, an 18-year-old from the Philadelphia area.

Ben, who uses they/them pronouns, is a life-long unschooler who grew up alongside three sisters who homeschooled, unschooled, and attended a local self-directed education center (Open Connections). Ben was the only “always unschooled” sibling. Ben’s initial interests were coding and robotics, but videography soon took center stage, and at age 14, Ben created a video about unschooling that gained almost 400,000 views.

More recently, Ben has worked at Whole Foods, started creating a 20-minute mini-documentary, and nearly completed the requirements for the Pennsylvania state homeschool diploma. Two of Ben’s sisters are now in college (and another is on her way), but Ben’s not currently interested in following their footsteps. Instead, Ben is partnering with their girlfriend Genevieve (who I met at Not Back to School Camp in 2022) to embark upon a 9-month cross-country roadtrip to create an 8-part video series about unschooling and self-directed education. Inspired by documentaries like Approaching the Elephant, Self-Taught, and Class Dismissed, Ben is passionate about producing new, high-quality video content about self-directed education, especially from the perspective a young adult unschooler.

Thanks to Ben’s professional communication style (I’m a stickler for thoughtfully worded emails!) and how closely their goals align with my experience and interests, I was delighted take them on as a pro-bono mentee. As part of the deal, Ben and I also agreed to share publicly about the mentorship process. This is my first of four quarterly posts about our year-long mentoring relationship. You can find Ben’s first report (a video, naturally), here:

Being genuinely useful to a young person whose struggles you understand is one of the delights of mentorship.

Ben’s big project, right out of the gate, was to raise money for the roadtrip+documentary through a crowdfunding campaign. As someone who has funded three books (and two smaller projects) through crowdfunding campaigns—and even written a crowdfunding guidebook—I immediately empathized with their looming challenge. We dove right in.

Not only was Ben trying to raise money as a relatively unknown young filmmaker—they were trying to raise $18,000! That’s quite the chunk of change, which motivated me to give their crowdfunding campaign a close, critical eye. Over multiple Zoom meetings in January we discussed wording, timing, perks, pricing, choice of platform, choice of funding model, and most importantly, how to get the word out. In February our discussion continued over email, as I was now in Patagonia without reliable internet. On March 3rd the campaign launched and made steady forward progress. Throughout March I was largely focused on running my Patagonia Retreat as Ben and Genevieve put in a ton of legwork, emailing over 500 people in their promotional efforts. By the end of the month their hard work paid off and they reached their $18,000 goal. Green light!

In our most recent call, Ben and I discussed how to make the most of this crowdfunding success, namely as a way to build relationships that lead to future friendships, partnerships, and work opportunities. I heard how Ben’s efforts to promote the campaign on TikTok resurfaced a number of common unschooling tropes (what about math? what about socialization?), leading them to wonder how “basic” an approach to explaining self-directed learning the documentary might need to take. And we discussed what happens in the two months between now and this summer, when Ben and Genevieve begin taking bigger, higher-commitment steps.

Outside of this exciting moment in the life of a young filmmaker, Ben remains a thoughtful 18-year-old who is actively considering big life questions: What route do I want to take after this project? Where do I want it to lead? Do I want to end up in one place or keep moving? How might I continue walking this unconventional path that I’ve been on? We agreed to keep these big-picture considerations in mind as we move forward, so I don’t just become an honorary project manager for the roadtrip/documentary. This mentoring relationship has already proven quite meaningful and satisfying. I’m looking forward to whatever comes next.