How to Read Difficult Books

We've all been there. You pick up a book that's been praised universally and you start reading it with the enthusiasm of a toddler reading her first book.


But this enthusiasm doesn't last long. Soon you start losing focus and your relationship with the book starts waning. Words and sentences don't make much sense, and you start wondering if your dedication is worth it.

Working Your Way Up

It could be that the book is out of your league. The authors of the acclaimed How to Read a Book: The Classic Guide to Intelligent Reading point out:

Good books are over your head; they would not be good for you if they were not. And books that are over your head weary you unless you can reach up to them and pull yourself up to their level. It is not the stretching that tires you, but the frustration of stretching unsuccessfully because you lack the skill to stretch effectively. To keep on reading actively, you must have not only the will to do so, but also the skill—the art that enables you to elevate yourself by mastering what at first sight seems to be beyond you.

There is, however, some merit in leaving a book midway if you already understand the underlying philosophy and realize that the author has made it more wordy than needed. Seasoned readers do it all the time.

But if you're someone who doesn't finish difficult books often, it's worth putting in the time and effort to go through them.

Don't Interrupt the Flow

You should start by reading it at one go, without looking up words you don't understand and without re-reading sentences or paragraphs you didn't quite get.

What is the right approach? The answer lies in an important and helpful rule of reading that is generally overlooked. That rule is simply this: In tackling a difficult book for the first time, read it through without ever stopping to look up or ponder the things you do not understand right away.

Why this approach? Well:

What you understand by reading the book through to the end—even if it is only fifty percent or less—will help you when you make the additional effort later to go back to the places you passed by on your first reading.

And even if you never go back, understanding half of a really tough book is much better than not understanding it at all, which will be the case if you allow yourself to be stopped by the first difficult passage you come to.

Changing the Habit

It's amazing how we're never taught this approach in schools. I recall sitting with a dictionary while reading Rushdie's Midnight's Children when I was in high school, and I gave up after slogging through a quarter of the book. The authors of How to Read lament this practice:

Most of us were taught to pay attention to the things we did not understand. We were told to go to a dictionary when we met an unfamiliar word. We were told to go to an encyclopedia or some other reference work when we were confronted with allusions or statements we did not comprehend. We were told to consult footnotes, scholarly commentaries, or other secondary sources to get help. But when these things are done prematurely, they only impede our reading, instead of helping it.

That's why I never really got the hype around Shakespeare's work and was confused as to why it were a part of our curriculum. It's only later in my life did I realize what a genius he was.

The tremendous pleasure that can come from reading Shakespeare, for instance, was spoiled for generations of high school students who were forced to go through Julius Caesar, As You Like It, or Hamlet, scene by scene, looking up all the strange words in a glossary and studying all the scholarly footnotes. As a result, they never really read a Shakespearean play. By the time they reached the end, they had forgotten the beginning and lost sight of the whole. Instead of being forced to take this pedantic approach, they should have been encouraged to read the play at one sitting and discuss what they got out of that first quick reading.

Changing the habit of interrupting your reading flow should probably be the first step in your mission to conquer difficult books.

Skimming Could Help

I've never tried this but skimming a book and spending more time with its table of contents and preface could help you get clarity on whether the book is worth your time.

Skimming or pre-reading a book is always a good idea; it is necessary when you do not know, as is often the case, whether the book you have in hand is worth reading carefully. You will find that out by skimming it. It is generally desirable to skim even a book that you intend to read carefully, to get some idea of its form and structure.

This would, understandably, only hold true in case of non-fiction books. Skimming a fiction book would be akin to fast-forwarding a movie that you haven't watched; why would you do that?

Don't Miss the Forest for the Trees

Reading a difficult book at one go the first time you read it can be a liberating experience. It's about letting go. You will have to force yourself to not check words or double-tap them on your iPhones. But it's worth it in the end. Otherwise, as one of my favorite lines from How to Read a Book points it out beautifully:

You will miss the forest for the trees.