Short Little Difficult Books
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The article 'Short Little Difficult Books' discusses the value of reading challenging literature, sparking a discussion on HN about personal favorite difficult books and the benefits of reading complex literature.
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Nov 18, 2025 at 9:23 AM EST
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I sometimes half-jokingly maintain that Moby-Dick was really written as part of an early BOOK-IT [1] reading incentive program to improve literacy among whalers by disguising a novel as a cetological guidebook.
There are entire chapters devoted to the harpooning process, sperm whale anatomy, maritime legal disputes over whale harvesting, etc.
[1] - https://en.wikipedia.org/wiki/Pizza_Hut#Book_It!
> [1] - https://en.wikipedia.org/wiki/Pizza_Hut#Book_It!
Talk about nostalgia. Haven't thought about pizza hut and book it in ages.
Another personal suggestion in this vein: The Queue by Vladimir Sorokin (trans. Sally Laird), which consists entirely of unattributed dialogue. It's challenging at first but once you get a feel for the rhythm and start recognizing characters by how they speak, it becomes a really charming read.
And a counter point, Blood Meridian by the same author. Extremely difficult for no reason whatsoever. Terrible book.
Many people believe this is the mythical "Great American Novel" we've been arguing about and/or anticipating forever. Strong argument for that because it's actually very Hollywood, isn't it? It's an absurdly action-packed cowboy-horror mashup that's full of gratuitous violence and manifest destiny.
I know several people that thought it was "extremely gory for no reason whatsoever" and did not finish for that reason, but none that thought it was difficult. I was surprised TFA mentioned it in that light, because I remember Child of God being more of a slog and BM being a page-turner.
https://en.wikipedia.org/wiki/Great_American_Novel
As far as "for no reason", I would say that McCarthy's impressionist prose that meanders, leaves out some details while focusing on others, etc., is some of the best English language prose ever written. It's beautiful and conveys affect better than almost anything else I've encountered. All the "reason" I needed.
The book definitely covers evil and nihilism thoroughly, so why would you want to read something like that? Well, for every bad decision someone makes in the book, the reader has the opposite response of, "oh crap, don't do that!" So reading about nihilism doesn't make you more nihilistic. While I thought it was a great book it isn't something you should just read without consulting outside sources.
The other books mentioned (Gatsby et al.) really require context, but literal pigs sitting down to dinner with powerbrokers is something a 14yo can grasp.
My teacher tried to talk me out of it, but I insisted and ultimately she let me do it because Billy Budd is very a short novella.
To this day, Moby Dick is still my second favorite book of all time (with my all time favourite being The Lord of the Rings). I only read it once, 20 years ago, for a book report but it really stuck with me.
Part of it is growing up, but part of it is (obviously) that plays aren't meant to be read. There's a lot of detail and tone that doesn't really come across properly, and it sucks the life out of the story. Not sure why it's such a common practice in school.
I realize I'm probably wrong about my assessment, but I've tried to watch performances of his plays as an adult and the outcome is always the same: His words just sound like random noise to my brain. They bounce off.
And yet I love Cormac McCarthy. Blood Meridian is one of my favorite novels. Go figure.
Listening to Joyce read it aloud: https://m.youtube.com/watch?v=M8kFqiv8Vww&pp=ygUcam95Y2UgcmV....
I had so much trouble trying to read him before understanding the intended pacing. It's more poetry than prose.
Ok, this nerd-sniped me. Are we saying this now? Feels like a reference. Found it: https://lareviewofbooks.org/article/against-high-brodernism/
WTF? If the term is about superficial depth wouldn't the bros be into like, abridged graphic-novel adaptations of difficult Russian classics, and not actually diving into genuinely difficult stuff regardless of quality? Shouldn't highbrow literary types sneer with greater cleverness or at least clarity?
> I also find it strange to even worry about “pretentious” readers or “brodernists” hyping themselves up to read some new, huge tome (Schattenfroh this season it seems) in an age when few people read anything at all. Reading a very long book always takes some dedication, some challenging of yourself. So what?
Ok good, TFA actually does get it
—Apes don’t read philosophy!
—Yes they do, Otto, they just don’t understand it!
Not fiction or difficult, but I suggest Calvino's "Six Memos for the Next Millennium". It's novella-length lecture series for writers/readers, but I'd say it's really a critical/creative framework that's as relevant for math as it is for myth, or novels, or code.
If you like Ubik, Martian Time Slip might also pass as difficult.
https://en.wikipedia.org/wiki/The_Exegesis_of_Philip_K._Dick
>Not fiction or difficult, but I suggest Calvino's "Six Memos for the Next Millennium".
Thanks for the recommendation. Grabbed it too. Now back to the Fs in my Penguin Classics list...
Pynchon short stories: https://en.wikipedia.org/wiki/Slow_Learner
Delilo has many short ones including some of his best: https://en.wikipedia.org/wiki/White_Noise_(novel), https://en.wikipedia.org/wiki/Americana_(novel)
Haddon's breakthrough: https://en.wikipedia.org/wiki/The_Curious_Incident_of_the_Do...
DFW's breakthrough (maybe pushing it on "short" though) https://en.wikipedia.org/wiki/The_Broom_of_the_System
Ludwig still the reigning champ of short/difficult: https://en.wikipedia.org/wiki/Tractatus_Logico-Philosophicus
Sure, there is the middle part ("books are supposed to be fun and the world is so awful why would you want to suffer"), but I took the bit about negative judgment to be the main thing the author was complaining about.
You could read fiction for personal growth and non-fiction for fun as well.
My native tongue is French, so in my case it was Rabelais' "Gargantua" (~1500) and "La Chanson de Roland" (~1100). Both books require some motivation to get used to their respective languages. After a while, I could read almost fluently Rabelais' prose ; it was immensely funny, coarse and impudent. Roland was harder to grasp, I had to use a specialized dictionary, but it's a concise and epic tale, and I read some verses so many times I ended learning them by rote.
Even translated, some short books from a very different culture far in the past can be challenging. For instance "Eugene Onegin" or "Gilgamesh". As a counterpoint, "The art of war" is an easy read, though written 2300 years ago in a small kingdom of China.
A last comment: the author conflate books that are difficult because of a technicality in their writing, and those that are strange in their story. The translations of Abe Kobo or Kafka I've read had nothing difficult in their words, but the surrealist plots were very unsettling. In "Pedro Páramo" the reader feels lost in a harsh world and unsure of reality. Meanwhile, Perec's "La disparition" or Becket's "Molloy" are more about style tricks.
Greek, on the other hand, has lifetimes' worth of good stuff in its ancient forms, and can really reward the time spent in learning to read them.
It's not that I cannot get through it; I most certainly can. It's just not enjoyable for me to do so. I read ~100 books a year largely for enjoyment and I simply cannot enjoy something that is a slog to do.
Our school books have all had some (very helpful) translation work applied to the original text.
I'd assume that in French they're tough going for a while until you get your head 500 years back. I'm currently battling my way through Don Quixote in Spanish and though it's a fun and funny (not at all short) read, some of the long twisted sentences (and the old words) can be brutal. I'd bet, as above, that the English translations are breezy. I'm thinking about trying one after I finish this.
In French I'm currently working my way through Voltaire's Micromégas (which is short) but it's a hundred and some years after Rabelais and the prose is really concrete. Very short words and simple sentences. It's the story that's interesting.
It's been somewhat disappointing researching the reading habits of people who read many books a year. For the reader who tears through ebooks on Kindle Unlimited, they mostly read genre fiction in a few categories. The same thing has been happening to me. I used to challenge myself to read "the classics" but lately before bad I reach for genre fiction written at an 8th grade level.
For many, reading is just another form of entertainment. Maybe call it the hollywoodification of books? While it's far better form of entertainment than TikTok or Instagram, the true potential is in its ability to make us smarter by challenging our thoughts and dieas.
When books are seen as just another entertainment product in a saturated marketplace, why chose something which makes you struggle?
* Exit, Voice and Loyalty - about how organizations and people work. Easily the best social science book I've ever read
* Art & Fear - gives a much better model for creating software than most books
As an example, Vygodsky's 2-vol "Mathematical Handbook" (Elementary Mathematics & Higher Mathematics) and Yavorsky & Detlaf's "Handbook of Physics" have ungodly amounts of knowledge in a relatively small size books.
You can get them (and more) from https://mirtitles.org/
Handbook Of Physics – Yavorsky, Detlaf - https://mirtitles.org/2022/06/27/handbook-of-physics-yavorsk...
Mathematical Handbook – Higher Mathematics – Vygodsky - https://mirtitles.org/2022/06/02/mathematical-handbook-highe...
Mathematical Handbook – Elementary Mathematics – Vygodsky - https://mirtitles.org/2011/09/12/handbooks-of-mathematics/
Am I doing something wrong here?
In particular various kinds of formal experimentation can be quite fun and I wouldn't perceive them as difficult at all (especially in shorter form). I read a short story in multiple-choice form years ago and loved it. I've read most of Milorad Pavic's books, all of which have unusual formal structures (e.g., Dictionary of the Khazars has the nonlinear structure of a cross-referenced dictionary or encyclopedia). Some were a bit baffling (they also can fall into the "confusing events, surrealist dream logic, and elliptical plots" category) but I didn't find them difficult exactly.
One of the more common practical difficulties that can add friction to a book is a complex storyline with many characters who can be hard to keep track of. But this won't make the book as a whole feel super difficult as long as the content is worth it. War and Peace is a classic example of this, with multiple intersecting storylines and a large cast of characters. A Suitable Boy is a modern example in a similar vein.
But I think a lot of times when people say a book is difficult they just mean either "gosh I actually kind of have to pay attention to this" or "this is really long". To me those things actually are positive qualities if the content of the book is good, since they just make it richer. My favorite novel is In Search of Lost Time, which is one of the quintessential "difficult" books, but if you get into its rhythm, most of it is blissfully engrossing.
A few things I think fit into the "short little difficult books":
Borges is not someone I consider too difficult, but many do for the same reason the author mentioned people finding Calvino to be difficult. His works require that you invest some curiosity into thinking about the scenarios in his fiction. He also plays with the nature of the narrative of the story in a sometimes postmodern way that is still accessible. None of his works are longer than 20 pages or so, so not a huge time investment. I would recommend buying the Penguin "Collected Fictions" edition. It contains a collection of books of stories, and I would recommend prioritizing reading the Fictions and The Aleph collections first. Some of his popular stories to start with would be "Tlön, Uqbar, Orbis Tertius", "The Lottery in Babylon", "The Library of Babel", and "The Immortal". If you want slightly more sentimental, "The Circular Ruins" is wonderful. If you want dryer, more satirical and postmodern, "Pierre Menard, Author of the Quixote" is hilarious.
If you want a book that plays with the basic structure of a "novel", Nabokov's Pale Fire is a great read and a good introduction into what the technique of an unreliable narrator can truly achieve. No matter how out-there you think your interpretation of it is, if you look into published literary analysis of it, the rabbit hole goes so much deeper than you might think.
Gene Wolfe is highly regarded among science fiction fans, and for good reason. While he's best known for his Solar Cycle, a set of a dozen novels, I think that the best introduction to him can be found in his short stories. They might not seem difficult at first, but some of them, especially Seven American Nights, Forlesen, and the trio of stories in The Fifth Head of Cerberus, are similar to Pale Fire insofar as they are far more than they seem on the surface. They require some degree of scrutiny and interpretation from the reader. I wish I had read them before his bigger novels, as I found reading those novels was so much more rewarding after learning how to read Wolfe from his short stories. If you want to buy a few short story collections, there's going to be some unavoidable overlap, but I would recommend "The Best of Gene Wolfe" (for The Island of Doctor Death and Other Stories, The Death of Dr. Island, Forlesen, Seven American Nights, Death of the Island Doctor), "The Island of Doctor Death and Other Stories and Other Stories" (Tracking Song, The Doctor of Death Island), and "The Fifth Head of Cerberus" for its three novellas.
If you want something much more difficult, try J.G. Ballard's The Atrocity Exhibition. He was influenced by Burroughs (Naked Lunch would be another recommendation here if you can stomach the Beatnik depravity within) and wrote a novel that will challenge its reader in many ways. It's very interesting to go straight from this into Crash, which covers a lot of the same material in a less difficult structure. Baudrillard praised Crash with "After Borges, but in another register, Crash is the first great novel of the universe of simulation", but I would say The Atrocity Exhibition deserves this praise(?) just as much, even if it's much rougher around the edges. Certainly, the political stunt pulled using one of its sections (called Why I Want to Fuck Ronald Reagan) belong more to the Situationists' games than Baudrillard's universe of simulation, but the stunt relies just as much on the hyperreal breakdown of signifiers as anything Baudrillard even pointed to.
Extremely tortuous phraseology. But I finished it, with gritted teeth at 15.
I have long since abandoned the desire to finish every book I start. Life is too short.
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