Rabbitholes as Portals
Musing #7 | Fall down the right ones
"Down the rabbit hole" is an English-language idiom which refers to getting deep into something, or ending up somewhere strange. Lewis Carroll introduced the phrase as the title for chapter one of his 1865 novel Alice's Adventures in Wonderland, after which the term slowly entered the English vernacular ... The idiom is often used to describe a person who is researching a topic on the internet or exploring new things on the web.”1
Before I ever was in “tech,” I already knew a lot about it. I would find myself going down rabbitholes learning about it. Not because anyone was telling me to, but because it was a natural gravitational pull. I was curious about a lot of things in the tech ecosystem. Curious about the idea of creating something that scales from scratch. Curious about melding creativity with productivity. Curious about consumer as a category. Curious about what a career as an entrepreneur entailed.
Granted, after having experienced tech from the “inside,” I know a lot more than I once knew. A lot more about how to actually make something with any kind of tech in it. And I have a lot more confidence about what I know and whatever it is that I don’t yet know. But I also reflect that the rabbithole knowledge I had before was quite powerful. I was able to learn a lot from following my innate curiosity with abandon. And I’ve had this same kind of realization across a lot of different topics (namely certain niches of business, fashion, film, writing, and human behavior ).
Rabbithole knowledge is the hyperspecific stuff you learn about a particular subject without any obvious need to know it. It's not related to your field of study. It's not related to a degree you're seeking. It's not related to a job you have. It's not related to a person you're trying to impress. Rabbithole knowledge is just the result of a strong gravitational pull of curiosity that can’t easily be explained.
Good things come from going down rabbitholes. Rabbitholes have the potential to be powerful portals into worlds that you don’t yet know that you deeply care about. That you care about being a part of not just for a moment, but in a meaningful way. I'm convinced that your enduring passion lies in the rabbitholes you've been down or will go down — if you just let yourself fall.
Telling the rabbitholes apart
Trap or Portal
Some rabbitholes are traps. Because the curiosity that led you down them was the wrong kind of curiosity. Going down a rabbithole because you’re curious about a subject is good. It's about learning for no purpose other than to learn. But going down a rabbithole because you’re competitive — because there’s a game you’ve identified that you just want to win — is a weaker, more dangerous signal.
There are an infinite number of rabbitholes that you can fall down in pursuit of winning a game. If that’s the sole goal, you’re likely to keep bouncing from game to game without a healthy anchor. You're likely to get rabbithole whiplash. Traps are also dangerous because you can end up spending years in them despite not seeing a long-term vision that you want. And they’re more prone to causing burnout because there’s less intrinsic drive. I’ve probably spent years of my adult life falling down rabbitholes where I was optimizing for winning some game. Where I got sucked into the microcosm I fell into and the bigger picture got hazy.