How To Read Big Difficult Books (Plus Recommended Reading List)

I’ve read my fair share of the heavyweights. From Plutarch to Proust, Conrad to Camus, and Dante to Dostoyevsky. I used to struggle with the “greats”. After a few pages, I’d close the book with a headache and poor sense of self-worth. Was I stupid? Maybe I needed to return to Dr. Seuss and retake my entire literary education…

Well, I wasn’t stupid. I was just approaching these books the wrong way. Big difficult books remain inaccessible to most people for a reason: they require a unique set of reading tools and a completely foreign approach to reading. Unless you’ve dedicated a lot of time to tackling these works and managed to make it through the frustration, you probably don’t know exactly what is needed to appreciate them. That’s because no one ever tells you. But I’m going to tell you right now so you can dive right in and start enjoying the big once-formidable classics.

How To Read Big Difficult Books

Here are the tips that I have learned through years of trial-and-error and stumbling through the classics. Follow this approach and you will be able to knock quite a few hefty volumes off your book bucket list. You’ll actually enjoy them and remember them too!

Read Slow

Don’t rush to consume big difficult texts.

Don’t treat them like holiday reads.

You aren’t stretched out on a sun lounger thumbing through the latest Jackie Collins. You’re reading Thoreau or Shakespeare or Homer. This is work. And you need to do your work properly. No half-assed jobs here.

Big books aren’t badges to be collected for honour (though you can enjoy boasting about your literary conquests later).

There’s no point blasting through the classics if you can’t recall or discuss them.

Oh, yeah, I read Ulysses but I can’t remember any of the central themes, protagonists, plot or whether I enjoyed it = pointless.

Big books are journeys to be savoured.

Difficulty demands attention.

Don’t make Melville contend with Netflix in the background. Go to a quiet room, sit up in a relaxed but alert posture, and pay careful attention to exactly what you’re reading.

There is no shame in re-reading the same sentence several times. In fact, it is absolutely 100% to be encouraged. When you’re reading Flaubert or Chaucer or Faulkner, you are reading poetry. You are reading le mot juste. You should totally savour each sentence as though you were weighing a fine wine on your palette.

Read a sentence, ponder, appreciate, read it again. Slow down.

These aren’t books for speed-reading.

I remember in Oxford I was up against a deadline, so I took three Thomas Hardy novels to the library and spent 4 hours trying to speed-read through them. I left the library with a headache, no memory of what I had read, and a misplaced hatred for Hardy. This was a totally different approach to how I had originally read Tess, savouring each sentence like a wonderful delicacy, leaving me with great fondness for Hardy.

Need help slowing down? Check out this book:

Reading Like A Writer by Francine Prose

That book will show you how to appreciate a work on every level – from words, sentences, and paragraphs to narration, character, and dialogue.

I also thoroughly recommend these two books for learning how to appreciate great literature:

Use Study Guides

My “dirty secret” for how I aced my Oxford University entrance interview and received an invite to the best university in the world?

I used study guides.

I can’t remember the exact guide I used back in my student years but one that I use and love today is Schmoop.

I was preparing to discuss some pretty weighty texts like Heart of Darkness and As I Lay Dying. Although I had views of my own, consulting study guides really solidified things like symbols and themes and characters in my mind. They helped ground my opinions in the sociopolitical context of the time in which the book was written, furthering my understanding.

These study guides are also great because, in addition to giving you a bunch of history surrounding the book, they will often include in-depth analysis about specific chapters. Finding chapter 33 difficult? Consult a study guide.

I recommended many of my students do this when I was teaching English. One of them asked: “Isn’t that cheating?”

No. It is not cheating!

Don’t rip off what other people write but you absolutely should use these materials to further your own understanding of texts and help develop your own opinions.

You think anyone who successfully made it through Ulysses did so without consulting a single exterior source? Hell no. That book is confusing as hell and you need to know a ton of stuff about mythology and ancient works just to get through it. There have been whole books written for the express purpose of deciphering what the heck Joyce was doing and people still don’t know everything.

You’ve gotta get some help when you’re tackling the big guns. Don’t be a lone guerrilla soldier against a world-class army.

Look up facts
View lectures
Read companions

Don’t know a specific ancient city place name or reference when reading Homer? Look it up. You’ve got something at your finger tips that the greatest scholars in the world didn’t have just a few years ago: the internet. Put it to good use.

Finding Ulysses confusing? Invest in a companion like this one. It will greatly improve you appreciation, understanding, and enjoyment.

Don’t know where to start with Chaucer, Dostoyevsky, or Homer? Check out The Great Courses for some really addictive and illuminating lectures.

Write Notes

I mentioned this already:

10 Ways To Retain More Of What You Read

You have to deface your books.

Cover your books with notes, opinions, underlinings.

Also get a notebook and fill it up with quotes and ideas.

I can’t tell you how many times I have not understood something and yet the moment I write it down it clicks. Writing helps consolidate and clarify understanding.

I even deface my pulp books. I’m reading Where are the Children? by Mary Higgins Clark and I’m covering that book with annotations. I’m treating it like a great work and I’m getting so much more out of it.

When it comes to big difficult books, scribbling in the margins is even more important because it will really help you tackle them.

This isn’t a quirk for us common lay-readers either. Look through history at all the great writers’ book collections – from Twain to Woolf to Hemingway – and you will see that they were all prolific note-takers. They covered their copies of Shakespeare and Homer. If they did it, you need to do it too.

Make Your Peace With Not Understanding Everything

A lot of stuff will go over your head. And that’s okay.

When approaching a big book, go into it with the mindset that you will read slow, learn around the subject, and take notes. But also know that these books are formidable for a reason.

It might take you years to fully consolidate the knowledge you get from these books. You don’t have enough knowledge from other areas to understand everything right away.

You’re going to miss a lot. But that’s something we all must deal with. We all have gaps in our knowledge. The aim isn’t to try and plug everything up – because that’s impossible – but to enjoy the process of filling in a few blank patches here and there.

If you can take just one valuable lesson from a book, that’s a win.

Start With The Easier Ones

You probably don’t want to go from reading Twilight one week to diving straight into Wittgenstein’s Tractatus Logico-Philosophicus the next. That’s only going to dishearten you.

Build your way up. Many of the “big” authors have smaller, more accessible works that should be read before diving into their magnum opus. If you can find some short stories by the author, try those before the big works.

Here are some examples for how you can start with different authors:

Conrad: The Secret Sharer -> Heart of Darkness -> Nostromo

Foster Wallace: Consider the Lobster -> Infinite Jest -> The Pale King

Joyce: A Portrait of the Artist as a Young Man -> Ulysses -> Finnegans Wake

Burroughs: Junky -> Naked Lunch -> The Soft Machine

Dostoyevsky: Notes from Underground -> The Gambler -> The Brothers Karamazov

Break Them Down Into Manageable Chunks

My Oxford Tutor, James Methven, a great intellect and award-winning poet, told us to read one page of Moby Dick every day.

Just one page.

That takes, what, 5 minutes at most if you really savour it?

If you manage 3-4 pages per day, you’ve read that classic in a year.

That’s how you conquer the white whale.

Big Difficult Book Recommended Reading Lists

Okay, now you know how to approach big difficult books, you’re now faced with the decision of what to actually read. Don’t worry. I’ve got you covered with five suggestions that I have personally loved. Pick one that takes your fancy and commit to really understanding and appreciating it. Read a little each day. Read slowly. Read around the subject, watch lectures, and make notes. Very soon, you will conquer the beast, have a damn good time doing it, and can move onto to your next adventure.

Moby Dick – Melville: This was one of the most rewarding and thoroughly enjoyable reading experiences of my life. I recommend you read a chapter a day whilst listening to the Big Read audio version. A bunch of public figures got together and crowdsourced the reading of this classic. Listening to Melville’s words whilst taking them in with your eyes and heart is truly magical.

You can read Moby Dick here.

The Grapes of Wrath – Steinbeck: Although not the biggest of the big reads, Grapes of Wrath is pretty dense and requires some forehead-wrinkling concentration. I recommend you start with Of Mice and Men first, which is a much slimmer introduction to Steinbeck and can be enjoyably finished within an hour or so. After that, get a good companion, check out some study notes, and saddle up for the big ride.

You can read The Grapes of Wrath here.

War and Peace – Tolstoy: What better way to obtain lifelong literary bragging rights than ploughing through this Russian doorstop? War and Peace is truly one of the biggies. I recommend resigning yourself to the fact that you probably aren’t going to finish this over a couple of lazy weekends. This one takes some real stones. I’m still working my way through it myself. What has helped me so far is getting a really good audio version to listen to while reading at the same time. I recommend the version narrated by Neville Jason.

You can read War and Peace here.

Blood Meridian – McCarthy: This book is not for the faint of heart. Really. If you’re looking for a classic that will make your stomach heave and make you lose all faith in humanity, this is it. If you haven’t read McCarthy before, I recommend you start with All The Pretty Horses or The Road as a primer and then dive into this one. Be warned with this one. Even the most well-read academics in the world have abandoned this one.

You can read Blood Meridian here.

King Lear – Shakespeare: Everyone needs a bit of Shakespeare. Why not tackle one of his best? The key to getting to grips with Shakespeare is to actually see live performances. My appreciation of this play would be a fraction of what is is if it weren’t for experiencing the wonderful Pete Postelthwaite production, watching Peter Brook’s bleak film version, and learning the history under one of the best literature teachers of all time, Tim Dearmer.

You can read King Lear here.

Happy Reading

That’s all I know about reading big difficult books. Let me know what mammoth you decide to tackle and how you get on!