floating online,
touching grass,

Reflections on organizing a rabbit-hole-athon retreat

life retreat curiosity

For some context, a couple of months ago, I tweeted this

The idea seemed to resonate with a lot of people and 4 of us decided to try to make it happen, which began the process of setting up a website, application, finding sponsors, an AirBnB etc.

This past weekend, it actually happened.

picnic forest walking campfire

Still feels surreal that an idea turned tweet actually happened. When does that ever happen? We’re excited to continue using Rabbit-hole-athon as a platform for fostering a space for curiosity, learning, fun, and vibes.

Some random reflections on on organizing the event and interesting discussions we had during the event

  1. It’s very hard to build a good (online) community from scratch. It’s surprisingly effective to build a (online) community from a memorable in-person event.

  2. There are lots of things everybody wants to do, but few people are willing to be proactive and take the initiative about (approaching someone, organizing events, saying hi first etc.). You can expose yourself to incredible experiences by being a person that does the latter. Be a person that does things.

  3. Games are a surpisingly effective way to help people bond. They’re also really fun.

  4. Being vulnerable with each other remains the best and fastest way to connect with other people. There are different types of vulnerability and they all compliment each other - there’s personal vulnerability (sharing personal things or experiences), emotional vulnerability (sharing how you feel about things), idea vulnerability (sharing your opinions and ideas, however popular or unpopular they are), etc. If friendship is shared understanding, then vulnerability is the vehicle through which you achieve that.

  5. The most sustainable and fun form of learning is learning driven by curiosity.

  6. You can get better at thinking by just doing a lot of it.

  7. Everyone has stuff (thoughts, ideas, hot takes, opinions etc.) to share, being a good conversationlist is about how to give people the space to do so.

  8. Teaching is a form of storytelling, where the teacher is trying to plant questions in a student’s mind that the teacher will then go on to answer. It’s like the teacher has a trail through the dark forest, but the student can only discover it by first feeling around in the dark until they understand where to go, the teacher can guide, but the student must walk. If the teacher tries to drag the student down the trail before they are ready, they will trip, fall, and miss the big picture.

  9. Writing is to thinking and understanding as solving problems is to math.

  10. Dating is hard and confusing.

  11. Laughter is one of the most powerful emotions at effectively bringing a group closer together.

  12. A little bit of boredom goes a long way to create space for original ideas.

  13. Everyone is incredibly interesting and has experiences that are so different to everyone else. There’s a word for this. Sonder: the realization that each random passerby is living a life as vivid and complex as your own. The depth and intensity of some people’s experiences continues to surprise me.

  14. The vibes of a community or event is as much a result of the people / participants as the organizers. If the latter are not energetic, the former may never be.

  15. The bottleneck to most things is knowing it’s even an option, either you read about it, talk about it with someone, get exposed to it through other people who already know about it - how do we make more people aware of what they’re capable of doing?

  16. Forests are incredibly dynamic, complex input-output systems. They’re kind of like PID controllers.

  17. I’m so grateful for the internet. If you don’t enjoy your use of Twitter or the Internet, you can change and curate your experience to enjoy it. As harmful as social media can be, you may never find a more effective way at meeting cool, like-minded people, and doing cool stuff. It’s worth investing a little time to figuring out how you want to use it (in a way that’s healthy) when the ROI can be so positive.

  18. Most things in life are in fact a balance between opposing forces. Extremes are rarely the correct approach. This is why giving advice is tricky because advice is usually binary (i.e. do this one extreme) as opposed to readjusting the balance (i.e. doing a little more of one, a little less of another) between those two forces. For example,

  • being constantly in a rush vs. taking things extremely slowly.
  • working very hard vs. relaxing and enjoying life.
  • wasting time all the time vs. never wasting any time.
  1. The world is so incredibly small. Everyone knows everyone. Everything is connected.

  2. People irl are rarely like the perception of them that you build through their digital presence.

If spending a weekend vibing, learning, and diving down rabbit-holes sounds like something you’d want to do in the future, please let me know :)