“Rabbit hole”
What a wonderful term—thinking about it gives me a warm and fuzzy feeling. The literal meaning, of course, is a rabbit’s burrow, but it’s the figurative meaning that truly captivates me.
“Rabbit hole” carries many connotations, both positive and negative. In colloquial use, “going down a rabbit hole” means being so absorbed by something that time flies and you end up in places you couldn’t have imagined before.
In its positive sense, it’s a rewarding experience where you learn or discover something new. In its negative sense, it’s wasting time learning about disturbing, fringe, or conspiratorial ideas.
The credit for popularizing the phrase “down the rabbit hole” goes to Lewis Carroll, the author of Alice’s Adventures in Wonderland. “Down the Rabbit Hole” is the title of the first chapter, and this is how it begins:
Alice was beginning to get very tired of sitting by her sister on the bank, and of having nothing to do: once or twice she had peeped into the book her sister was reading, but it had no pictures or conversations in it, “and what is the use of a book,” thought Alice “without pictures or conversations?”
So she was considering in her own mind (as well as she could, for the hot day made her feel very sleepy and stupid), whether the pleasure of making a daisy-chain would be worth the trouble of getting up and picking the daisies, when suddenly a White Rabbit with pink eyes ran close by her.
There was nothing so very remarkable in that; nor did Alice think it so very much out of the way to hear the Rabbit say to itself, “Oh dear! Oh dear! I shall be late!” (when she thought it over afterwards, it occurred to her that she ought to have wondered at this, but at the time it all seemed quite natural); but when the Rabbit actually took a watch out of its waistcoat-pocket, and looked at it, and then hurried on, Alice started to her feet, for it flashed across her mind that she had never before seen a rabbit with either a waistcoat-pocket, or a watch to take out of it, and burning with curiosity, she ran across the field after it, and fortunately was just in time to see it pop down a large rabbit-hole under the hedge.
In another moment down went Alice after it, never once considering how in the world she was to get out again.
The rabbit-hole went straight on like a tunnel for some way, and then dipped suddenly down, so suddenly that Alice had not a moment to think about stopping herself before she found herself falling down a very deep well.
Delightful, isn’t it?
I came across this quote by the French poet Stéphane Mallarmé some time ago, and it became etched in my memory:
“Everything in the world exists in order to end up as a book.”
If I were to paraphrase this quote, I’d say:
“Everything in the world exists in order to end up as a rabbit hole.”
This is what I believe, and each passing month continues to strengthen that conviction. Put another way: how can you live without wanting to know something? How is that a good way to live? You might question the point of knowing random things. To which I ask: what’s the point of living if you don’t want to know random things and give in to that urge?
If you don’t go tumbling down a thousand rabbit holes, time travel to distant lands and universes from the comfort of your home, and come back transformed, have you even truly lived? It is in those distant places and times that we find the tools and ideas that allow us to create the meaning we all desperately crave, whether we realize it or not.
Whatever we’re seeking in life, whether conscious of it or not, lies down one rabbit hole or another. Viewed this way, diving down weird and wonderful rabbit holes isn’t just a deliberate activity but is the very essence of being and living.
Why?
I don’t have some sophisticated answer. I like knowing things for their own sake. Goalless exploration is fun. Why pollute the fun of random discovery with ulterior motives? Whoever said that you need a reason for everything? The best things in life are the result of randomness, and that applies to both our real lives and our intellectual lives. A good life is one that allows serendipity to find you, say hello, and then slap the shit out of you. I’m a misguided romantic that way, and I like being that way.
So how do you find rabbit holes to tumble down?
You don’t.
I won’t offer some platitude like “the rabbit holes find you.”
The necessary precondition for finding a rabbit hole is a ripple. Think of a ripple as a sign, a mental buoy, a North Star, or a mental gravitational tug on your attention. Ripples direct your attention toward something, and rabbit holes are downstream of that. That means you need to direct your attention at something, and for that you need ripples that catch your attention.
Though the word has been overused, I believe curiosity is an essential element of a life well-lived. Curiosity suffers from imprecise definition. To me, curiosity isn’t the mechanical acquisition of knowledge but rather an orienting force, like gravity, pushing you toward where “good things” await discovery.
Several months ago, I had read this post by the thoughtful
Adam Robbert
, in which he calls attention “first philosophy.” It landed with the force of a nuclear bomb in my mind, and I haven’t stopped thinking about it since.
Attention is first philosophy—
Philosophy is not only a system of thought but a mode of attentiveness, an exercised openness to what exceeds us yet calls us to deeper participation. Its systematic aspects are downstream of this attentiveness, and can certainly become a scaffolding by which others can train their own attention, but it is at its root a mode of cultivated attention.
After reading it, I initially wanted to argue that curiosity, not attention, is first philosophy. But I was wrong. Curiosity doesn’t emerge in isolation. To be curious, you must first notice things—ripples—so attention truly is the foundational philosophy.
So what you need to notice about ripples are two things:
-
You need to do things that create ripples in the vast universe of your mind. That means the first thing you need to do is do things and be in places that can create ripples in your head. So unless there’s some randomness in the way you learn, there won’t be any ripples.
-
Once there are ripples, you need to pay attention, and that’s where the next transformative rabbit hole awaits. To paraphrase the Greek philosopher Heraclitus: “No one falls down the same rabbit hole twice, for it’s not the same rabbit hole, and they’re not the same person.”
First comes a ripple, then a rabbit hole.
Every possibility for wonderful things happening in your life flows downstream from a ripple. The right ripple can lead you to learn and experience things your imagination could never have conceived.
Let me share a few examples from my experience. This post led me to read War and Peace, and it’s the best book I’ve read so far in my life. I was playing around with AI coding tools like Claude Code, and I built this site for a passion project I’d always dreamed of creating: collecting great historical letters in the public domain. That urge in itself was due to another ripple—reading Shaun Usher’s newsletter. Building this site led me to discover Seneca’s letters, which were so good that I built a simple site to make them easily readable.
Just one beautiful line in Poetics of Space inspired me to start reading poetry again, and it’s been a profoundly rewarding experience. These are just a few examples, and I can keep going. The best thing I’ve done in the past few years is to build rituals and follow people who can create ripples. For instance, whenever I read Maria Popova, it’s impossible to read just one of her posts; I inevitably tumble down multiple rabbit holes.
The Substack app feed has become another place for discovering amazing rabbit holes. Just this morning, I came across
Nicholas Gruen
’s post, and I found two new rabbit holes—a podcast about Hannah Arendt and a quote by W.B. Yeats. Then there are other sites like Aeon, LRB, and even Twitter, for that matter, that always have something fascinating on offer.
Perhaps one of the most delightful side effects of going down rabbit holes is that they force me to write. I can’t help but write about whatever fascinating thing I discover in a week. Rabbit holes help me discover things worth writing about, and writing helps me discover things worth reading—it’s a virtuous loop.
Naturally, all this leads to questions like going deep vs. wide, what to focus on and what not to, information diets, optimizing your reading (whatever that means), and so on. I love being indiscriminate about the rabbit holes I pursue. I don’t know if that’s a good thing or a bad thing, but it works for me. More importantly, it’s fun, and it never feels like a chore.
One annoying thing about the Substack feed is the deluge of posts claiming to teach you how to read more, optimize your information intake, become smart in 87 seconds, read like René Descartes, or think like a philosopher. Whenever I’m feeling insecure, I end up clicking some of these posts, and I always feel like shit because I feel inadequate. Then I realize most such content is clickbait nonsense, and I go back to scrolling for my next link.
Optimize for ripples.
Everything else is gas.
Image: Giuseppe Arcimboldo, The Librarian, c. 1566, oil on canvas, Skokloster Castle, Sweden.