On Reading Difficult Books

Is there a book that you want to read but scares you? It’s too long, or too technically demanding, or its subject matter is challenging — is there such a book on your virtual or physical bookshelf?

I have several such books waiting to be read. I also make a point to read several such books each year. They’re nearly always worth the effort.

Goodreads and its annual reading challenge make readers favour short, quick reads, skim reading and light reading. This is not by chance, but this isn’t a post about the failures of Goodreads as a platform. This is a post about reading difficult books, and the point is that if you want to challenge yourself you’re going to have to make a concerted effort on your own.

You will have to motivate yourself because reading platforms and book clubs skew towards books that can be read quickly and relatively easily, and we’re being trained daily to shorten our attention span and ruin our capacity to concentrate and think by platforms like TikTok, Instagram and YouTube. To read difficult books is to go against the grain, to retrain your mind to deep, meaningful thought, to long stretches of concentration, to a higher level of empathy. It’s the difference between a fast food burger and an evening with a 3 star Michelin chef showing off his best work. It’s worth it, but it costs more.

If you chose to go on that challenging but worthwhile journey, here are some tips to help you along the way:

  • Build up to it – don’t start with the toughest, longest, scariest book on your list and try to white knuckle your way through. Build up to it by stretching and building up your reading and concentration “muscles” first. If you’re building up to length, for example, fantasy and space opera sci-fi novels are a great way to get there, as they’re usually well paced, relatively easy reads. Historical fiction and family sagas can train you to follow multiple timelines and characters, and short stories utilizing modernist and post-modernist techniques can offer an easier way to encounter them for the first time.
  • Have a light read going simultaneously – this is particularly effective if the book you’re tackling has a difficult subject matter. Have a light, fun read going on at the same time and switch between the two, allowing yourself a break from the difficult topic and time to process it every once in a while.
  • Find a partner for the journey – find a friend, online or in real life, who’s interested in reading the same book as you are, and help each other through it.
  • Find a community – it’s difficult to find a friend interested and able to dedicate time to take the reading journey with you, but it may be possible to find a community of readers going through the book at the same time as you are. It can be through a local bookclub, a virtual bookclub, a reddit community, a Goodreads group, a discord channel – whatever group you can find and suits you. Just make sure you’re comfortable with the group rules in terms of code of conduct and spoilers, and feel free to leave if you encounter toxic behaviour.
  • Create a framework to help you through – ideas for this can include various trackers, reminders, applications like Forest or other Pomodoro like counters that help you focus, little treats or incentives after reaching certain milestones. If I’m reading a particularly long book, I set up a dedicated tracker and a page count I want to hit every day, to make sure that I don’t feel overwhelmed and can visually see my progress. It somehow helps me deal with the goblin in my mind that is screaming that this book is too much for me and I don’t have time for it. Field notes are great for this, especially the squared and reticle grid ones.
  • Start by reading a good chunk – on your first read at least the first chapter or several chapters, so that you get into the flow and tone of the book as soon as possible. I tend to aim for 30-50 pages on the first sitting.
  • Get a physical copy of the book, not a digital one. Paper books are easier and more enjoyable to read than digital ones, as our mind finds them easier to process because of the way we read (oftentimes returning a page or two back to check on something, or flipping to a previous chapter to remind ourselves who that character is or what happened last time). Whenever I’ve tried to read a difficult book on my Kindle, I’ve regretted it (The Alexandria Quartet is the latest example).
  • Feel free to give up, tomorrow – if the book is too much for you, it’s OK to decide that you’re not going to finish it, or you’re going to get back to it at a later date. But before you do that, take one more day to make an effort and read another chunk anyway. Why? Because you may have just reached a particular tough spot, and in a few pages things clear up, or become easier to digest. Also, you may just be having a bad day, or you’re particularly distracted or tired and so the writing becomes more opaque or more of a slog. Give it another day and if it doesn’t improve, move on.
Tracker for Paul Auster’s 4321 on a Field Notes Snowy Evening with a Spoke Design pen.

I’m currently reading Paul Auster’s 4321, which is a challenging read due to its length and its structure. Later on this year I plan to reread James Joyce’s Ulysses (I read it twice cover to cover already, and studied it while taking my degree). I’m considering tracking my rereading here, in case someone wants to follow along. Let me know in the comments if that’s something that may interest you.

9 thoughts on “On Reading Difficult Books

  1. Raffaello Palandri

    I confess to a distinct aversion to “light” reads. This isn’t a casual preference; it’s a yearning for depth. I crave intricate sentences that unfurl like puzzles, demanding close attention. Challenging topics ignite my curiosity, and intricate wording becomes a map to unexplored territories within the text. This affinity naturally draws me towards non-fiction, where complex ideas take center stage.

    I find satisfaction in unraveling complex sentences, dissecting them to grasp their full meaning. It’s a mental exercise, a workout for the intellect that leaves you feeling invigorated. Simple narratives often paint life in broad strokes. I, however, seek the richness of detail, the subtle shades of meaning that intricate wording reveals. It’s like viewing a landscape through a magnifying glass, where hidden intricacies come to light. Light reads often prioritize entertainment over intellectual engagement while I crave books that challenge my assumptions, that present complex ideas that demand contemplation. These books spark discussions, ignite debates, and often leave me enriched with a new perspective. 

    This isn’t just about reading; it’s about a love of learning, a desire to engage with the world on a deeper level. Complex books become your companions on this intellectual odyssey, each one a gateway to a richer understanding of yourself and the world.

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    1. Daphna Kedmi

      Thank you Raffaello. You have perfectly put into words my dissatisfaction with “light reads” and my preference for those reads that are a challenge, that require concentration, what I refer to as pencil reads, with markings all over the place and questions to myself that I know I will have to rethink once I finish reading the book. Not all tough reads are necessarily good reads, but I find that light reads, of the best seller type, don’t captivate me and very often bore me.

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  2. Daphna Kedmi

    I pretty much agree with you except for the recommendation of simultaneous light reading (see Rafaello’s comment). When I am immersed in a book, I find it very difficult to read something else at the same time; I’m all in and don’t want to be away from it.
    I also have an issue with abandoning books which is, of course, completely my problem. If I’m having difficulty with a book that reviewers I respect have strongly recommended, I feel that I should give it a chance, and I never know when to draw the line and say to myself, leave it already.
    I’m having this problem with Susannah Clarke’s Jonathan Strange & Mr. Norrell that I’m reading now. I’m reading it because I loved her Piranesi. This one, written 10 years before Piranesi is very highly recommended, but 300 pages in (it’s 700 pages long), it’s not working for me, and everything tells me to abandon it and move on. But I keep thinking that just a few more pages and it will open up to me, it must. And that’s how I’ll probably end up reading it through. I see that as a reading weakness of mine.
    The Alexandria Quartet and the Books of Jacobs are gearing up on the starting line.

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    1. writingatlarge

      I completely understand the difficulty of giving up on a book. I used to be unable to do it. I’m now kinder to myself and appreciate my time and effort more, and so I gave up on Christie’s worst book ever, and I’ve allowed myself to take a break with the Books of Jacob (though I will likely return to it).
      Some books just aren’t worth it, and some don’t connect with us, in the same way you may or may not enjoy a work of art or piece of music despite its technical genius or historical importance. I have just come to be more accepting of that with time.

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      1. Daphna Kedmi

        Nofar, you got me at “kinder to myself”, and after a few more pages, I let it go, וראה זה פלא the sky didn’t fall…

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  3. Richmond Road

    What would one define as ‘light’ reading? To refer to something as ‘light’ strikes me as a bit condescending – there is a certain arrogance that is implied by insisting upon reading the ‘heavy’ stuff. I used to bury myself in old Russian stuff as a teenager, but I find them impenetrable now. I loved Piranesi, by the way. I read The Sisters Brothers, by Patrick DeWitt not long ago and was very moved by it, though one wouldn’t call it ‘heavy’ reading, surely? Hemingway was delightfully easy to read – more recently Vonnegut or Tom Robbins or, indeed, Patrick DeWitt.
    So by ‘light’ I am thinking you mean genre based stuff – pulp fiction.
    But if authors are trying to be too clever, or mysteriously complex, I tend to treat them with great suspicion.

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    1. writingatlarge

      No, I actually don’t mean that, and I find your assumption that I treat genre literature as light to be condescending. There was no judgement in this post, please refrain from imposing any on it. This was about encouragement not disparagement.

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      1. Richmond Road

        Oh, goodness …. I didn’t mean to offend. All I was trying to say was that these things are very difficult to get a handle on, such is the nature of art, and one never knows which oysters might contain pearls. My suspicion is that ‘difficult’ books are often obliquely praised for their difficulty, when that characteristic is actually their main failing.
        I’d like to stress that there is a big difference between ‘difficult’ and ‘nauseating’ – books that do tend to reside in different sections of the bookstore.
        Once again, I apologise for any implied expression of condescension. Such was not intended. I have been on the receiving end often enough myself.

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