Why You Should Read Difficult Books And Take This Test To Find Out

Home » Legacy ETC Playbook » Curiosity » Why you should read difficult books (and take this test to find out your reading level) So how should you choose your next tome? Well according to this little article from Huffpost, you should pass on the easy ‘holiday’ reads and head straight for the ones which challenge you. I’m talking those big idea books, or those books that delve so eloquently into a subject that you might even get a mild headache. The books that require the endurance and dedication of an ironman competitor. Commenting on one particular complicated but competent read, the author commented;

“The one I’ve just finished, The Sellout by Paul Beatty. It won the 2016 Man Booker Prize and was widely praised and adored, presumably by people who are more amenable to a challenge than I am. Set in the southern outskirts of Los Angeles, The Sellout was a witty, funny, extraordinarily clever book, with a strikingly original take on racism, slavery and segregation.” “And while I was repeatedly astonished by its intelligence, pausing to re-read slabs of text that had captured a truth perfectly, or marvelled at a perfect turn of phrase, I found it hard to... It almost seemed as if it was too dense with cleverness. I just found that reading it felt a little like work, or like reading an article about the history of the Israeli/Palestinian conflict that was informative, and hugely worthwhile, but a slog.

At least it was a lot funnier.” In our modern era of instant information and bite-sized entertainment, reading intellectually challenging material can seem like an unnecessary burden. Why struggle through a dense classic novel, a difficult philosophical treatise, or an intricate historical account when easier, more accessible options are available? However, those who embrace the challenge of “hard books” often find their intellectual lives enriched in ways that lighter reading simply cannot provide. In the context of classical education, where the cultivation of wisdom and virtue is paramount, reading hard books is not just beneficial — it is essential. Reading a difficult text requires patience, focus, and perseverance.

When a book is challenging, the reader cannot simply coast through it in a passive way. Instead, he or she must engage actively, rereading passages, looking up words, and considering complex ideas. This process strengthens the mind much like physical exercise strengthens the body. In an age where attention spans are shrinking, the discipline developed through reading demanding works is invaluable. A student who has struggled through The Republic by Plato, The Scarlet Letter by Nathaniel Hawthorne, or The Canterbury Tales by Geoffrey Chaucer will develop the ability to sustain deep thought. This intellectual stamina prepares individuals for rigorous study in any discipline, whether in law, medicine, theology, or philosophy.

Even more importantly, it enables them to engage with the weighty questions of life with clarity and insight. Many of the greatest works of literature, philosophy, and theology do not provide easy answers. Instead, they invite the reader into a serious intellectual and moral struggle. Consider Augustine’s Confessions, where the author wrestles with questions of sin, grace, and divine providence. Or regard Shakespeare’s Hamlet, which raises profound questions about justice, revenge, and the meaning of existence. These works challenge us not just to understand but to engage, to debate, and to form our own reasoned conclusions.

By reading hard books, we learn that truth is not always simple. Life’s most significant questions — What is justice? What is virtue? What is the good life? — are not easily answered. Grappling with these texts prepares us for the complexity of real-world ethical and philosophical dilemmas.

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. I’m a self-proclaimed avid reader (and audiobook listener), which has been a core part of my life over the last few years. However, I find myself gravitating towards the same literary genres, or books that I would describe as falling within my comfort zone: self-development, business, fitness/nutrition, and my guilty pleasure, psychological thrillers.

My love of reading started off as a hobby, but has now turned into a big part of my workday. What started as one hour in the morning with my coffee quickly turned into 2 hours, and eventually became 3-4 hours per day. Over the last 6 months or so, I really started expanding my horizons—diving into new genres, disciplines and tackling more difficult reads. While this takes significantly more self-discipline, patience, and an active reading habit, the payoff of getting through these challenging books has made it all worth it. Last summer, I attempted to read Ulysses by James Joyce without any sort of primer—I just read the back of the book and the introduction (which included a short history of the text). I thought I had prepared myself for this literary beast by reading some classic literature prior, including authors like Oscar Wilde, Slyvia Plath, Ernest Hemingway, and Fyodor Dostoevsky.

I was feeling confident, and obviously niave. After struggling hard through the first two chapters, I abandoned Ulysses entirely—feeling perplexed, discouraged, and slightly cross-eyed. While Farewell to Arms took me a bit to warm up to in terms of style, understanding the narrative, and getting to know the characters, with Joyce, I was completely lost and had no... If you’ve read—or attempted to read Ulysses, then you know what I’m talking about. I decided to try my luck again this year by picking it up again for the second time, but approached it in a completely different context. I just finished Ulysses last week; my hardest read to-date which provided the inspiration for this article.

For those that aren’t familiar with Joyce or his work, Ulysses is a modernist novel that was published in 1920 and is considered “the marathon of literature.” Joyce is known for mixing different narrative... He pushed barriers in language, and was prolific for his lack of censorship, and for incorporating controversial views or “taboo” topics into his work (ie. his sacrilegious views on the Roman Catholic Church). For example, in episode 14 (Oxen of the Sun), Joyce showcases the gestation of the English language by combining prose that spanned Latinate alliterative Anglo-Saxon, medieval, Elizabethan, early seventeenth-century, and Gothic prose…among others. Trust me when I say that this was by far the hardest chapter. It seems obvious why textbooks are hard to read.

The material is dense; there’s a lot of information packed into relatively few words. Authors often feel obligated to give you a broad, complete understanding of a topic rather than to weave an interesting story from selected details. Teachers are ready to assign a textbook, even if it’s boring; it’s seen as a regrettable but unavoidable problem. But there’s a more subtle reason that it’s hard to stay engaged when you read a textbook. To find out why, read this paragraph, one you might find in a typical high school textbook. The Manhattan Project was the United States’ effort to produce a nuclear weapon, and it was the largest construction enterprise in the history of science.

Because of its sensitive nature, a massive effort was made to keep the project secret. Famous scientists traveled under aliases; Enrico Fermi was known as Henry Farmer, for instance. And all telephone conversations at the test sites were monitored. Despite those efforts, historians agree that it probably would have been impossible to keep the secret if not for the fact that the project was of relatively small size. Did you notice that the last sentence contradicted the first? Embedding a mistake or contradiction into a text and seeing whether readers notice it is a common research technique to measure comprehension.

Readers are asked to judge each text on how well it’s written and explain their rating. Readers are very likely to notice a word they don’t know. They are also very likely to notice if the grammar of a sentence is wrong. But they are much less likely to notice when two sentences contradict each other. Forty percent of high school students missed the contradiction in the paragraph above. To put it another way, if readers simply understand each sentence on its own, they figure they are doing what they’re supposed to do.

Lately, I’ve been thinking a lot about why we should read those “difficult” books— the ones that challenge you and make you sweat a bit trying to figure them out. I know, I know, it’s tempting to stick to the easy stuff, especially when you don’t have much free time and responsibilities are calling. Growing up, I had no problem picking up lengthy books, but once I got into college I had so much studying to do that any book above the 400-page mark used to be a... The same went for classics, fantasy epics, and anything on the philosophical side. But that has long since changed. And I’m glad because embracing challenging reads anew opened up a whole new world of literature for me.

You see, you might not finish these books in a single sitting (okay, you definitely won’t). You’ll probably find yourself re-reading paragraphs, pondering sentences, and reaching out for your dictionary. They might make you sweat a bit, but the payoff is huge. Books, particularly novels, have many different purposes. Some may aim to transport us to a different country, world or universe. Others help us to relax at night after a particularly harrowing day or to provide an alternative perspective on life.

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