How To Fall Down A Reading Rabbit Hole
Or, the art of having a weird little interest
Curiouser and curiouser!
You are a baby sitting in a highchair making gentle but enthusiastic cooing noises while a spoonful of mush is brought closer and closer to your face. Airplane noises are made to further entice you. The hand holding the spoon is the set of algorithms that determine all the content you’re fed every day. The flavor of mush is whatever the algorithms think will get you to take another bite. And you love your mush, so you do. You take bite after bite in the form of funny memes, reaction videos, podcast clips, and increasing amounts of AI slop.
You are now a 400-pound algorithmically stuffed baby. One imagines that the high chair breaks under your weight. The algorithms do not mind. The algorithms are happy to feed you while you roly-poly all over the floor.
Much has been written about algorithms and their impact on our media consumption, but I am not qualified to add anything to the corpus. I have used the word algorithm seven times already and not once did I spell it correctly on the first go. What I am qualified to do is recommend something to help you reclaim a modicum of agency as a consumer of information.
Become a rabbit hole reader.
Through the looking glass
What do I mean by rabbit hole reader?
I mean find a sub-genre of books that you really love and dive in headfirst. Just like some home chefs are most comfortable with Italian red sauce dishes and others can knock your socks off with a butter chicken, I think as a reader you should cultivate your own specialty. And unlike the chefs, who might be expected to share what they cook regularly with hungry family and friends, there’s no expectation that anyone has to know what you’re into, so feel free to get weird with it.
Some people like historical fiction. Some people inhale Romantasy books. Some people only read business and professional development books, and those people are wrong. They should be put on a list so we know who they are. But that’s a different article. My recommendation is to take something you already like and go buy two or three books in the same category.
For example, I absolutely (and morbidly) obsess over the memoirs of the dead and dying. Regularly remembering that our time here is limited (memento mori) helps me focus on the big things while disregarding petty annoyances. I can’t imagine what people go through when given a terminal diagnosis, especially when the bad news comes so unfairly early on in life, but I’m grateful for the brave individuals who don’t blink under the Reaper’s gaze and choose, instead, to share their experiences through memoir. When Breath Becomes Air, Tuesdays with Morrie, and The Bright Hour are all favorites of mine, but if I stumble on something new out in the wild, I get it. Different books will resonate more or less with me, but as a whole this strange, sad little niche is one I feel at home in.
(By the way, I shared two other sub-genres that I love over in my Reading List.)
We’re all mad here
But that’s just my rabbit hole. You need your own.
My guess is that you already have a weird genre you’re really into, even if you don’t know it yet. Go back over your reading list or your Goodreads if you have one. If not, think about your favorite books and what connections they have in common. Don’t worry too much about rigor here. Ender’s Game, Harry Potter, Looking for Alaska, and Never Let Me Go are all “boarding school books.” But take Ender’s Game and put it in a pile with Dune, The Picture of Dorian Gray, and Macbeth and instead the category is “winning ain’t all it’s cracked up to be.” Stories can be described via tropes for a reason; connections abound.
So is rabbit hole reading different from just having a favorite genre? To be honest, I’m not entirely sure. To me, it feels more specific and intentional. But most things are a matter of degree, and all that’s important at the end is that you make the list your own.
For example, I have one friend whose rule is that if he ever finds a book on the 17th-century philosopher Baruch Spinoza in the wild that he doesn’t already own, he must buy it on the spot. As you can imagine he struggles to find time to read all of his Spinoza books given the hordes of women knocking down his door, trying to date him.
Another friend collects books on the niche history of firearms and other weapons. And I mean niche. Like pay a strange man on Kickstarter multiple years ahead of time and trust that his passion for exploring the difficulties an Eastern Bloc country has in manufacturing their own AK-47s will eventually lead to a book you can prominently display in your home office. Is that book for many of you? No. But it is for my friend, because he has found his rabbit hole.
Now I imagine by this point some of you are asking yourselves “if the algorithm just gives me more of the same because it knows I already like it, doesn’t rabbit hole reading just make me the algorithm?” Congratulations, you’ve figured me out. See—I want you to become your own algorithm. I want you to become a specialist in finding things that make your own life richer. And I don’t want it to be because the machine thinks what it feeds you is all you’re capable of, but rather as a function of who you aspire to be in this life.
After all, while the goal of this piece is to get you to read more intentionally, rabbit hole reading can be applied to just about any form of media or consumption. Expertise starts with interest and taste comes from navigating specific passions. So if you want to specialize a little and books aren’t your thing, dive deep into the world of Greek vase paintings, or Bildungsroman films, or pick a favorite Gaelic football team and follow them obsessively. Soon enough you’ll figure out what makes something good or bad within your niche. Congratulations, you’ve become a little more interesting by being interested. So be weird. Be unique. Be you.
If you don’t know where you’re going, any road will take you there
Although I want you to come up with your own rabbit holes, I’m happy to get you started if you’re feeling stuck. Here are a few suggestions.
Read challenged books. A convenient way to quickly ascertain that you’re on the wrong side of history is to find yourself at a book burning. In 2025, we seem to have replaced the public bonfires of old with the seemingly more genteel yet no less insidious book challenges. Between 2001 and 2020 the American Library Association recorded a yearly average of 273 books targeted for censorship and removal. In 2023 the number was 1,247. While 2024 was slightly better at 821, we’re still multiples higher than where we used to be and there’s no end in sight. The ALA regularly publishes lists of books that are targeted and I think it’s a great rabbit hole to go down.
Read books on a discrete historical event or category. Maybe it’s a disaster like the sinking of the Titanic or the attacks of September 11th. Or you could go deep on the Battle of Gettysburg, Agincourt, or Thermopylae. Reading about a discrete event from different perspectives helps you see the situation in a new light and better understand the inherent biases in retelling history. Or you could go deep on a category—like I did with shipwrecks earlier this year. The HMS Wager wrecked in 1741, the RMS Lusitania was sunk in 1915, and the German submarine U-869 went down off the coast of New Jersey in early 1945. The circumstances of each loss were unique, but the deadliest enemy was always the sea itself. So ask yourself which Wikipedia pages you end up on again and again and go buy some books.
Read books that use a particular structure. For example, I go nuts for an epistolary novel. You’ve probably read some already even if you’re not familiar with the term. Epistolary fiction is literature constructed out of letters between characters, diary entries, or some other “found” text. Maybe you read Dear Mr. Henshaw when you were younger. The Screwtape Letters, Augustus, and Memoirs of Hadrian are all exceptional as well. Address Unknown can be finished in under an hour and is unfortunately relevant to our times. Something about the format and how it changes what the author does just works for me, but if it’s not your cup of tea there are plenty of other literary structures to dig into.
Do you have your own weird sub-genre you love? Or maybe recommendations for books I should read in the ones I love? Leave a comment or shoot me a note, I’d love to hear from you. And, as always, if this was forwarded to you and you’d like more, feel free to:
Cheers for now. We’ll talk again Thursday when I share the first edition of the Last Page, my roundup of media consumption from July, and again on Friday for another entry from the Weekend Read.
My algo to me: "I will pack your sweet pink mouth with so much content, you'll be the envy of every Jerry and Jane on the block!"
My reading rabbit hole recently has been esoteric fiction (Foucault's Pendulum by Umberto Eco, Journey to the East by Hermann Hesse) anything that has to do with bizarre symbolism and layered meaning where you have to let the mysticism and semiology wash over you.
Lastly, a mostly epistolary novel I read a few years back and loved: The Pale Blue Eye by Louis Bayard. Netflix released a film adaptation which I haven't seen, but the shifting perspectives of a retired police detective and West Point cadet Edgar Allan Poe trying to solve a murder was so well done.