What are the best ways to read a difficult book?

You should place the Big Book in a full nelson and take the damn thing to the mat. That should do the trick.
All joviality aside, I understand the trepidation that you feel when faced with a Big Book. I get a certain sort of quaver in my boots when I contemplate tackling Infinite Jest and Gravity's Rainbow. (Maybe someday…)
As someone who reads almost exclusively fiction, I can only speak with any semblance of authority (and not much at that) on literary Big Books. I hope that my advice will still glean some insight on how to approach the Big Books in the nonfiction world.
Know Thy Enemy (and Thyself)
This is a good time for a pithy Sun Tzu quote:
“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”
Books pose challenges for different reasons, particularly in literature. Some books simply use archaic language and anachronistic references, but are otherwise straightforward (Pride and Prejudice, "Hamlet," and "The Canterbury Tales"). Others make your mind spin because of the difficult and complex subject matter on hand (Infinite Jest, Gravity's Rainbow). A good helping of them are simply mind-numbingly long because the authors were paid per word and this is what happens (Anna Karenina, Bleak House, The Count of Monte Cristo). Many modern classics employ sophisticated–and at times, befuddling–narratives that defy chronology (100 Years of Solitude, The Handmaid's Tale, Cloud Atlas). The list goes on and on, but I won't turn this answer into a Big Book unto itself.
The root of a book's challenge tells you two things: how to approach it and whether it's worth it.
If you have a choice in the matter–in other words, this isn't an assignment for a course you have to take–you have to consider whether slogging through "The Canterbury Tales" on your own is worth deciphering the seemingly alien Middle English. (I say yes, but it's only because I'm a fan of 'The Wife of Bath.") If you don't have patience for decoding old English, perhaps Chaucer and Shakespeare aren't your cup of tea. Alternatively, if you love delving into a subject matter, go for the meaty literary heavy hitters like Infinite Jest and Gravity's Rainbow.
Once you decide that the Big Book is worth the fuss, you need the right mindset.
Go In With Guns 'Ablazing
As I said, different Big Books pose different challenges, therefore they must be read in different ways. Here's an incomplete lists of possible strategies:
Anachronistic Language – this is where purchasing an annotated book is a must. Nobody should face Middle or Early Modern English without assistance (and a stiff drink). It's also useful to go over the basic plot before reading so you can focus on the language. (Psst. A ghost tells Hamlet that his step-daddy killed his real daddy to marry his mom. He's kinda pissed.)Foreign Environs – some settings are so foreign to us modern folks that they seem downright inscrutable, such as Jane Austen's 19th century genteel ladies's society. This is where Google is your friend. If you read something that you don't understand, Google it! Complex Narrative – in some ways, your approach to convoluted narratives is the opposite to books with anachronistic langauge and settings. You can't get too caught up with the details since it's quite possible that the book intends that you not know where you are in time or place. It is, however, important to keep the overall story in mind. I had to do this with 100 Years of Solitude by keeping a family tree of the prodigiously large and confusing Buendia family handy at all times.Long and Boring – it's easy to lose your way in those books that exceed 800 pages. Don't be afraid to skim the more descriptive passages and go for the juicy stuff. Tolstoy and Dickens were just trying to earn a few extra bucks. Heavy Subject Matter – this is where prior research might be necessary for you to fully appreciate a book. Brush up on a little quantum mechanics before Gravity's Rainbow and a little on fractals for Infinite Jest. You don't need a Ph.D in those topics, but you should know what fractals are before jumping into Jest. Most references will go over your head so you'll have to decide whether to be a stickler and look each of them up or just go with the flow. There is no shame in getting an explanatory book (such as SparksNotes) for some of those books as long as you actually read the book.
Big Books pose challenges precisely because we are unfamiliar–due to context, language, subject matter, or style–with contents of the book. Extracurricular research is nothing to be ashamed of.
Do a Postmortem (Not the Bloody Kind, Please)
Big Books aren't the sort of books that you can toss in the recyclin9g pile upon completion. You'll still have to expend brain cells over this thing. Sorry, folks.
When I finished The Handmaid's Tale, I didn't quite know what to think. The last chapter completely changed how I saw the entire book (which was Atwood's intention), upturning my whole understanding of the book. I couldn't leave my reader self in such a confused state, so I went online to read essays about the endings, ask questions on reader forums, and even re-read the chapter. Only after this backwards examination did I grasp the book in truth.
After I finish a literary heavy hitter, I ask myself:
What in the hell just happened? (To get a sense of the plot.)Why did the author do such crazy things? (To ferret out, if possible, the point of the book.)Why is this book so well-regarded? (To figure out its significance in the literary canon.)Do I really think that this book deserves its acclaim? (To see if my opinion diverges from the scholarly conventional wisdom.)
An unexamined book is not worth reading

Answer by Cristina Hartmann:

You should place the Big Book in a full nelson and take the damn thing to the mat. That should do the trick.
All joviality aside, I understand the trepidation that you feel when faced with a Big Book. I get a certain sort of quaver in my boots when I contemplate tackling Infinite Jest and Gravity's Rainbow. (Maybe someday…)
As someone who reads almost exclusively fiction, I can only speak with any semblance of authority (and not much at that) on literary Big Books. I hope that my advice will still glean some insight on how to approach the Big Books in the nonfiction world.
Know Thy Enemy (and Thyself)
This is a good time for a pithy Sun Tzu quote:
“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”
Books pose challenges for different reasons, particularly in literature. Some books simply use archaic language and anachronistic references, but are otherwise straightforward (Pride and Prejudice, "Hamlet," and "The Canterbury Tales"). Others make your mind spin because of the difficult and complex subject matter on hand (Infinite Jest, Gravity's Rainbow). A good helping of them are simply mind-numbingly long because the authors were paid per word and this is what happens (Anna Karenina, Bleak House, The Count of Monte Cristo). Many modern classics employ sophisticated–and at times, befuddling–narratives that defy chronology (100 Years of Solitude, The Handmaid's Tale, Cloud Atlas). The list goes on and on, but I won't turn this answer into a Big Book unto itself.
The root of a book's challenge tells you two things: how to approach it and whether it's worth it.
If you have a choice in the matter–in other words, this isn't an assignment for a course you have to take–you have to consider whether slogging through "The Canterbury Tales" on your own is worth deciphering the seemingly alien Middle English. (I say yes, but it's only because I'm a fan of 'The Wife of Bath.") If you don't have patience for decoding old English, perhaps Chaucer and Shakespeare aren't your cup of tea. Alternatively, if you love delving into a subject matter, go for the meaty literary heavy hitters like Infinite Jest and Gravity's Rainbow.
Once you decide that the Big Book is worth the fuss, you need the right mindset.
Go In With Guns 'Ablazing
As I said, different Big Books pose different challenges, therefore they must be read in different ways. Here's an incomplete lists of possible strategies:
  • Anachronistic Language – this is where purchasing an annotated book is a must. Nobody should face Middle or Early Modern English without assistance (and a stiff drink). It's also useful to go over the basic plot before reading so you can focus on the language. (Psst. A ghost tells Hamlet that his step-daddy killed his real daddy to marry his mom. He's kinda pissed.)
  • Foreign Environs – some settings are so foreign to us modern folks that they seem downright inscrutable, such as Jane Austen's 19th century genteel ladies's society. This is where Google is your friend. If you read something that you don't understand, Google it!
  • Complex Narrative – in some ways, your approach to convoluted narratives is the opposite to books with anachronistic langauge and settings. You can't get too caught up with the details since it's quite possible that the book intends that you not know where you are in time or place. It is, however, important to keep the overall story in mind. I had to do this with 100 Years of Solitude by keeping a family tree of the prodigiously large and confusing Buendia family handy at all times.
  • Long and Boring – it's easy to lose your way in those books that exceed 800 pages. Don't be afraid to skim the more descriptive passages and go for the juicy stuff. Tolstoy and Dickens were just trying to earn a few extra bucks.
  • Heavy Subject Matter – this is where prior research might be necessary for you to fully appreciate a book. Brush up on a little quantum mechanics before Gravity's Rainbow and a little on fractals for Infinite Jest. You don't need a Ph.D in those topics, but you should know what fractals are before jumping into Jest. Most references will go over your head so you'll have to decide whether to be a stickler and look each of them up or just go with the flow. There is no shame in getting an explanatory book (such as SparksNotes) for some of those books as long as you actually read the book.
Big Books pose challenges precisely because we are unfamiliar–due to context, language, subject matter, or style–with contents of the book. Extracurricular research is nothing to be ashamed of.
Do a Postmortem (Not the Bloody Kind, Please)
Big Books aren't the sort of books that you can toss in the recyclin9g pile upon completion. You'll still have to expend brain cells over this thing. Sorry, folks.
When I finished The Handmaid's Tale, I didn't quite know what to think. The last chapter completely changed how I saw the entire book (which was Atwood's intention), upturning my whole understanding of the book. I couldn't leave my reader self in such a confused state, so I went online to read essays about the endings, ask questions on reader forums, and even re-read the chapter. Only after this backwards examination did I grasp the book in truth.
After I finish a literary heavy hitter, I ask myself:
  • What in the hell just happened? (To get a sense of the plot.)
  • Why did the author do such crazy things? (To ferret out, if possible, the point of the book.)
  • Why is this book so well-regarded? (To figure out its significance in the literary canon.)
  • Do I really think that this book deserves its acclaim? (To see if my opinion diverges from the scholarly conventional wisdom.)
An unexamined book is not worth reading.

What are the best ways to read a difficult book?

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