An Ode To Rabbit Holes

I’ve been reading The Psychology of Money by Morgan Housel. In it he mentions a quote from John Bogle (the founder of Vanguard and pioneer of index fund investing) where Bogle talks about the "relentless rules of humble arithmetic" and how high fee funds violate those rules.

This stuck in my mind as something I wanted to follow up on. What did he mean by “humble arithmetic”? What sort of investments is he saying you should avoid? I filed it away for another time.

I forgot about it until a couple of days later. I was doing an errand online and got bored. While mindlessly procrastinating on twitter I came across a post (I forget what it was) that made me think of the John Bogle quote.

I thought, “let me do a quick google search on that” — and so began my descent into a rabbit hole.  I emerged from the hole 1.5 hours later, interrupted only by noontime pangs of hunger.

What have I been doing for the past hour and a half?” I wondered to myself.  “Oh yeah, I went down another rabbit hole.

Going down rabbit holes — a common experience for any internet surfer. It starts innocently enough. You ask yourself, “What’s the name of that actor from the Karate Kid? Wonder what he’s up to now.” Next thing you know, you have 100 tabs open about Ralph Macchio and a plan to watch Cobra Kai on Netflix that evening.

Here are some rabbit holes people have gone down recently:

I love going down rabbit holes. Sure, sometimes it goes a little too far. Sometimes we feel indulgent or guilty afterwards for “wasting” time or “distracting” ourselves. But to me, it’s one of the best things about the the web — going deep, discovering new things, finding answers (or finding more questions), and learning from others.

There’s this wealth of deep, richly detailed... stuff out there, waiting for only our curiosity and willingness to look for it. It’s a beautiful thing.

I think you could even look at being in a rabbit hole as a way of entering flow — you can become so engrossed and interested that you lose track of time. That's when you get that "what have I been doing for the past 3 hours?" feeling.

I realized, though, that I haven’t really thought about rabbit holes much more than that. I got curious about them. How (and why) do we get into one? What do we do when we’re inside? What do we do with them afterwards?

Chasing the White Rabbit

Alice in Wonderland is a strange, wonderful, funny little book. It also happens to be where the phrase "rabbit hole" comes from. In the opening chapter, a bored Alice sees a white rabbit with pink eyes and a pocket watch hurrying somewhere and muttering to itself. She decides to follow him (funnily enough, the thing that catches her attention is a rabbit wearing a waistcoat and carrying a watch; not a rabbit that can talk.)

Next thing she knows, the rabbit slips into a rabbit hole. In she goes, and so begins her descent:

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.

That’s sort of how we get hooked, isn’t it? We're bored or procrastinating. Our mind is seeking distraction. We interact with something, online or offline, that triggers a thought, which maybe leads to another thought and so on. (In retrospect, I find it’s often hard to identify what triggered the initial thought.)

Eventually a thought sparks our curiosity — the white rabbit — and off we go, never once considering where it might lead.

Sometimes it’s less open-ended than this — for example, trying to find the answer to a specific question (when you're programming, writing, doing research, etc). I’ve had plenty of browser windows with 50 tabs open to figure out a hairy programming problem.

But the fun rabbit holes are the ones which surprise us as we fall down them. These ones often start as a distraction.

I’ve been spending energy recently trying to reduce how distracted I get online. I think it’s a real problem to being productive and thinking deeply, but it’s not all bad. How else do we discover new things? There’s a bit of a thrill to the feeling of exploration.

Distraction and discovery are, I think, opposite sides of the same coin.

Down the Rabbit Hole

"Either the well was very deep, or she fell very slowly, for she had plenty of time as she went down to look about her, and to wonder what was going to happen next."

Alice's fall towards Wonderland wasn’t fast — time slowed down for her. She fell slow enough to take down a jar of marmalade from a passing shelf and doze off along the way.

Time slows down in virtual rabbit holes too. As I fell down my Bogle Hole, I completely lost track of time because I was lost in the flow of what interested me.

Now the moment you've been waiting for – a flowchart of my Bogle Hole, constructed from looking at my open tabs, browser history, and from memory.

Unlike Alice’s descent in the book, which was linear, my exploration branches off everywhere, leads into adjacent topics, and opens several threads (that I still haven’t finished exploring). It started with reading a paper by Bogle; that piqued my curiosity further and opened up more branches.

Some things I noticed I do when I go down rabbit holes:

  • A lot of Google searches
  • Read/watch/listen
  • Follow links in articles, visit sites I hadn't heard of before, read/like/post on social media
  • Open a bunch of tabs (when I think I may want to go back to something, or I’m opening up a new thread of exploration)
  • ...but not necessarily a new tab for everything (sometimes I go back in browser history to revisit/refine a search)
  • Bookmark or otherwise save a subset of pages along the way
  • Maybe have some things I want to do later (in this case, I wanted to buy a copy of this book, and remember to read some articles later)
  • Maybe take notes (including copying snippets of pages I want to come back to later)

We've become so proficient in using browsers, that we do a lot of this without really thinking about it. I wonder if some of it could be made easier though.

Back up the Rabbit Hole

“Begin at the beginning,” the King said, very gravely, “and go on till you come to the end: then stop.”

Lunchtime. I came up the rabbit hole as easy as I went down, once my concentration was interrupted. After a nice lunch on another smoky Bay Area day, I sat back down at my computer. I wasn’t feeling the Bogle Hole vibes anymore. Now what?

I enjoyed learning about Bogle’s philosophy of investing, and integrating it into my own mental model of how I want to invest.  I liked that I came out of it with more questions and more topics to explore. What’s the “3-fund portfolio”? How would I implement this strategy if I did do it? What’s the deal with “Bogleheads”?

I have a bunch of tabs open, some topics I want to follow up on, a book I might want to purchase. But I don’t want to do any of it right now.

I think something is missing in our browser tools that could make this a more enjoyable and useful experience.

I want to save the good things I found along the way, keep track of new threads I want to follow in the future, and remember the things I want to do later.

‌Not sure I want to "drop back" into a hole later, but I’d like the option to. Maybe I want to see the full history of how I branched out in exploring the various topics. Maybe I want to save everything I found, or just pick and choose the most useful things. Maybe I even want to share some of it with others?

How do I preserve the knowledge, ideas, and connections I made?

Things that could be better

Some more thoughts on what the gaps in tooling seem to be:

Tab proliferation

Too many tabs means too much browser memory consumption and too much clutter. Things that would help me avoid this:

  1. I want to save things I found along the way (ideally mostly automatically), and make them findable and useful later. The lack of tooling here (beyond basic bookmarks) activates my FOMO and makes me want to hoard everything “in case I need it later.”
  2. I want a way to keep track of tasks I need to do later or things I want to read/watch/listen to later.
  3. I want to "freeze" a rabbit hole so you drop back to it later. It would be nice if I could have a way to take note of topics that were still pending more exploration, so I could unfreeze it and pick up where I left off.


It would be really cool if a tool could help me make connections between things I find in various rabbit hole explorations. What have I found in the past that might be related to what I'm looking at now? Can I explore, in an open-ended way, how information I've found online might be interconnected?

Info overload

When you’re deep in, there can sometimes be a sense of information overload. Suddenly it feels like there are too many threads to follow. How to explore, breadth-first or depth-first? How do I keep it all in my head? Wait, where did I see that other link?

How to keep track of everything I want to do afterwards and don't forget everything I want to remember? Am I really going to read all these articles or watch all these videos later?

Knowing when it’s enough

When do I stop? Sometimes an external interruption does this for you, but if not it’s easy to keep going deeper and lose track of time. Sometime after you haven't moved a muscle for hours and have lost all sense of the world around you, it turns from a “fun exploration” to “compulsive internet surfing.” I don’t want to lose sleep or deprioritize other important things in my life.

Curiouser and curiouser

“Curiouser and curiouser!” Cried Alice (she was so much surprised, that for the moment she quite forgot how to speak good English).”

All that said, there's a lot to like about rabbit holes. At their best, they are a conduit for our curiosity – fluid, open-ended, deep and generative.


They are fluid — they start someplace specific, but branch out and can lead to unexpected places. Relatedly, they can connect to other topics you’ve explored in the past.


Unlike the hole Alice fell down, there’s no real “end” to an internet rabbit hole, until you decide to end it. They end when something else takes priority, or you’ve learned what you wanted to learn, or you just get bored of it.

Not all explorations are like this; sometimes you're looking for a specific answer to something. But the fun ones are.


One of the rabbit hole’s defining features is you get deep. You find weird, niche sites and discover surprising details. It’s at once a testament to the internet’s massive breadth and bottomless depth.


They often produce a trail of new information, and generate new threads to explore. It’s not necessarily just about consumption — it can be an active process of understanding new information, finding what further piques your curiosity, and chasing another white rabbit.

Going somewhere

“Would you tell me, please, which way I ought to go from here?”
‌‌“That depends a good deal on where you want to get to,” said the Cat.
‌‌“I don’t much care where—” said Alice. ‌‌
“Then it doesn’t matter which way you go,” said the Cat. ‌‌
“—so long as I get somewhere,” Alice added as an explanation. ‌‌
“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”

As the Cheshire Cat says: a rabbit hole is bound to take you somewhere. That's often enough to make it worthwhile.

If you have rabbit hole stories you’d like to share, I’d love to hear them! I’m also actively exploring ideas to make web browsing better. If this interests you, please reach out. You can find me on twitter here.

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