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Organizing Rabbit-hole-a-thon

Last updated Aug 2, 2022

This past weekend some  modern internet friends and I organized a learning retreat. We called it rabbitholeathon.

From initial ideation, the weekend-long hackathon where  Amir and I hacked out the  rabbitholeathon website, and the scattered initial thoughts to rallying two other organizers to join our mission - this last weekend was the culmination of months of behind the scenes work. We decided to host the first iteration of the rabbitholeathon in Oshawa (an hour outside of Toronto). We brought together 18 curious minds from all across North America to humble Oshawa to learn together.

This was my first time organizing something like this, and my first time meeting so many internet people at the same time. I wanted to take some time after the weekend to reflect and recharge. Here are some of my big takeaways and memories:

  1. if you want something to exist, be the one that makes it happen. I’m not the first one to say this, this form of advice has been reshaped and reformed by many wise leaders. “Be the change you want to see…” etc. but it is valuable to remind myself of this frequently.
  2. sonder was a big theme over the weekend. Hearing everyone share their stories reminded us of how similar we all are while beautifully unique. Throwback to the senior year piece I choreographed with Nat Bernado on the word Sonder (maybe one of these days I’ll share more of my dance work here)
  3. nature has a way of making people relax - our WiFi was unstable throughout the weekend due to a hurricane in the area the prior week. So our retreat ended up being an offline affair in the woods of Ontario. While this was not the initial intention, the forced disconnect actually helped us bond and enjoy the nature around us more.
  4. kids that take gap years, drop out and unconventional paths seem to all have something in common – an unconventional relationship with home, parents, or upbringing. Most of us were working at startups, taking time off school, and doing super cool things that were different from our peers pursuing big tech or finance careers. I was surprised to hear many stories about participants’ family relationships or unique upbringings. It’s such a small sample size, and I have no scientific evidence but being far from home or having an unstable family relationship leads to young adults being more independent early on leading to more unconventional paths.
  5. building livable spaces is important. During the first night when we were sharing our rabbit hole areas of focus around the table, a common theme was building walkable cities, alternative spaces, and sustainable infrastructure. Like definitely attracts like - and our group had many similar interests in this area
  6. games can accelerate the formation of friendships. We played Fishbowl (similar to charades) and We’re Not Really Strangers throughout the weekend and they were definitely catalysts for how quickly the group bonded
  7. social media can bring people together IRL. This isn’t really a hot take but this weekend was truly a whirlwind. Crazy how 18 of us met online at one point and were all living under the same roof for a weekend. I still can’t believe it
  8. when money is tight, get creative. With the market downturn, some of our verbal commitments for sponsorships fell through and we found ourselves worried if we could still pull this retreat off. Luckily we found an Airbnb in Canada that was reasonably close to the airport and train station. We got creative with the venue landing on Oshawa because of the great cost, being able to use Canadian Dollars instead of USD, and proximity to the airport for participants to fly in.
  9. writing is one of the highest ROI activities you can do. This doesn’t just mean writing for others on a Substack, writing to collect your thoughts and refine your thinking can take you so much further than just passively consuming content.
  10. people in real life are so different from their social media and substack personalities. Fortunately for this group, everyone’s IRL personalities was a +10% to their online personas
  11. everyone knows everyone. I know this is an exaggeration but throughout the weekend, every time someone mentioned a mutual, we were all separated by at most one degree of separation. Insane.
  12. vibes are so important. the space around you, and the people you surround yourself with change how you think, feel, and act.
  13. be a doer. be the one that makes that event happen or that community thrives.

If any of this resonated with you, I’d love for you to join us at our next rabbitholeathon! Or be the one that makes this happen in your community. Be a doer.

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