University of Kwazulu-Natal

How To Read Big Difficult Books Plus Recommended Reading List

Bonisiwe Shabane
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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. 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! Don’t rush to consume big difficult texts. 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. When I first started reading non-fiction, I would only read books on self-help. I read obsessively, applied everything I could, and saw significant improvements in my life.

But by the tenth self-help book, I hit a massive reading slump. Everything sounded the same—just repackaged ideas with different authors, titles, and covers. Consequently, I no longer felt motivated or excited to read, and I convinced myself I had learned everything I could possibly know. One day, desperate to feel inspired again, I went to the bookstore. I browsed the self-help section first, but nothing stood out. So I kept wandering through the different sections: first psychology, then business, neuroscience, and economics.

As I weaved my way through various genres, wanting to read almost every book I encountered, it hit me: I had exhausted one subject but still knew nothing about countless others. Suddenly, the slump disappeared. I wasn’t bored or uninspired anymore. Instead, I was now overwhelmed by how much I didn’t know and all the subjects I wanted to explore. Despite wanting to take nearly every book home with me, I decided to be a responsible shopper and buy just one. I chose Thinking, Fast and Slow by Daniel Kahneman, a nearly 500-page book on behavioral economics.

I had no background in the subject, but I gave it a shot anyway. It wasn’t exactly beginner-friendly — dense with research and terminology that felt complex to me at the time — but I pushed through. Jeremy Anderberg • September 3, 2019 • Last updated: October 28, 2025 In the last year, I’ve managed to finish a number of lengthy, sometimes hard-to-read books. Ron Chernow’s 900+ page tome on George Washington. 600+ dense pages on James Madison.

Andrew Roberts’ massive biography of Winston Churchill. (Yes, I’m into biographies.) A couple of Dickens’ novels — they’re all big. Melville’s American masterpiece, Moby-Dick. Robert Caro’s legendary, epic series on Lyndon Johnson. And most recently, all 1,400+ pages of Les Miserables. Even though these books were enjoyable, and I had a genuine interest in the subject matter, they were often hard to read, if for no other reason than their sheer volume.

Large pages, small fonts, tiny margins. Les Mis, because of its actual weight, had to be read sitting up, and often in a chair with an armrest because the thing was so dang heavy and unwieldy. (While I could have read an e-version, as I’ll explain below, I often prefer hardbound copies of classics, even if they’re harder to wrangle.) While Hugo and Dickens are a delight to read, the reality is that their language is so different from today that it takes brain power to really digest. And while those biographies I mentioned aren’t necessarily old, they are dense with facts, especially when you’re new to that person/time period. They’re just intimidating for folks who aren’t used to that type of reading which requires sustained focus and a bit of endurance.

Before the last year or so, I would have probably counted myself in that camp. I had tried to read Washington: A Life and gave up after a few hundred pages. I’d tried Moby-Dick and met a similar fate. The allure of a big, meaty book was great, and yet I couldn’t find the stamina to actually finish many. Reading challenging literature can be intimidating, but it’s also incredibly rewarding. If you’re feeling stuck in your reading routine or eager to explore new authors and styles, you’re not alone.

Many readers struggle to dive into complex texts that push their literary boundaries. But what makes a book difficult to read? Is it the dense prose of modernist classics, the experimental narrative structures of contemporary fiction, or something else entirely? To tackle these questions, we’ll be examining some of the most difficult books to read, exploring strategies for engaging with them, and discussing the rewards of reading beyond your comfort zone. In this article, we’ll share expert analysis on complex literature, providing you with the tools to navigate even the most demanding texts and discover new favorite authors along the way. Whether you’re tackling the classics or diving into modern literary masterpieces, some books are notoriously tough to get through.

In this section, we’ll explore what makes them so challenging. When delving into some of the most challenging books to read, it’s essential to consider the complex language and narrative structures that can make them difficult to grasp. Authors like James Joyce and Virginia Woolf are notorious for their dense, lyrical prose, which is both a blessing and a curse. One of the benefits of using complex language in literature is its ability to evoke powerful emotions and create a rich, immersive experience for readers. The use of elaborate sentence structures and poetic descriptions can transport readers to new worlds and make them feel like they’re experiencing something truly unique. However, this complexity can also be overwhelming, making it difficult for some readers to follow the narrative.

For example, Joyce’s “Ulysses” is a novel that requires close attention and multiple readings to fully appreciate its complexities. Similarly, Woolf’s “Mrs. Dalloway” is known for its stream-of-consciousness style, which can be challenging to navigate for readers who are used to more traditional narrative structures. Reading dense, complex books can feel overwhelming, but having the right strategy can make the process easier, more engaging, and even enjoyable. Instead of avoiding challenging reads, you can break them down, use helpful tools, and stay engaged throughout the process. The key to success isn’t just pushing through difficult passages—it’s approaching them with a plan.

In this article, I’ll share my step-by-step approach to tackling hard books, from balancing your reading list to using ChatGPT as a reading assistant. Are you wondering how to read hard books? Schedule a Discovery Call to explore reading comprehension strategies for better retention. The first step in tackling difficult books is organizing your reading list to keep you engaged. If you only read dense material, you might burn out quickly. Instead, mix fiction and nonfiction so you can switch between heavy and lighter reads when needed.

Here’s how to structure your reading stack: 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... 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: You are here: Home » Blog » Bookworm's Notebook » How to Read a Difficult Book Reading books like Ulysses (1922) by James Joyce or Infinite Jest (2006) by David Foster Wallace can seem daunting, but it’s a journey well worth taking. Learning how to read a difficult book requires not just patience but also specific strategies to comprehend its complex themes and intricate structures. To face the challenges of reading a difficult book, develop a disciplined reading schedule and commit to reading a certain number of pages or chapters each day.

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