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 idea what the hell was happening. 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 styles, experimenting with language, and fusing different literary methods that span numerous periods in English literature. 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.

Much of his writing consists of stream of consciousness prose; an ongoing inner monologue regurgitated on paper that bounces from character to character. The narrative is frenetic and hard to follow, making this text read like a calculus textbook. An example in episode 11: Sirens with the theme of music is this: “Her wavyavyeavyheavyeavyevyevy hair un comb: ‘d”.

Another passage, sourced from the same chapter:

Hope he’s not looking, cute as a rat. He held unfurled his Freeman. Can’t see now. Remember write Greek es. Bloom dipped, Boo mur: dear sir. Dear Henry wrote: dear Mady. Got your lett and flow. Hell did I put? Some pock or oth. It is utterl imposs. Underline imposs. To write today.

I’m sorry, but what?

While I’ll be the first to admit that much of Joyce’s writing reads like a foreign concept to me, I was able to get through the text with much more ease by doing my due diligence from the outset of the novel. I did my homework to understand the major themes weaved within the text, which not only helped me decipher the novel, but also gave me a new found appreciation of the genius behind Joyce and the layers of complexity his fiction holds.

Guided by one of my favourite authors, Ryan Holiday, his approach to understanding difficult texts changed my approach entirely on how to read and absorb new, unfamiliar discourses. Following Ryan’s advice, I started reading more abstract and challenging pieces of work—mostly in the realm of philosophy and stoicism: Nietzsche, Marcus Auerlieus, Montaigne, and Plato, for instance.

In this post, I’ll share some strategies and tactics I’ve learned that have helped me better absorb the material and most importantly, make reading—in Ryan’s words— “above your level” more enjoyable. Since Ulysses is still fresh in my mind and this was the first book that I approached as an academic text, I’ll be using my experience as an anecdote to highlight examples throughout. But first, we need to deduce why you should even consider picking up books outside your scope of knowledge..

Why Read Difficult Literature

If we’re not forced to read challenging texts, then why bother? If you don’t have to run a marathon, why would you put yourself through that hell and torture? There’s a several reasons why picking up a difficult read can benefit us: it can help us grow—learn, unlearn, and relearn. From a personal challenge standpoint, pushing ourselves out of our comfort zone, helps us garner a strong sense of accomplishment and builds confidence. Reading hard texts will make you smarter, a better writer, more literate, and appreciate the literary brilliance behind a novel. We may even uncover a deep fascination for a new discipline and continue reading in the genre for pleasure alone.

While it’s true that easy reads are much more enjoyable and relaxing, challenging reads that have stood the test of time push you to think with a new frame of reference. Combining different disciplines can change the way you see and interpret the world, spark new ideas in your work, creative projects, relationships, and life. If you read only contemporary novels on trending topics, the knowledge extracted only runs skin deep. Will these books last the test of time or are their major takeaways ephemeral? Some people hold the cardinal rule that they’ll only read novels that were published 10 years ago or more. While I think that’s a bit extreme, there might be some merit in this approach. Reading perennial books can provide you with real, long-lasting knowledge, not just the latest hot tips from an IG influencer with 1m + followers.

Difficult Literature Makes Easy Reading More Enjoyable

I’m going to draw a Buddhist reference here because it’s so applicable to tackling difficult things in general. In one of my meditation classes, my teacher, shifu Yuan Jing, made us contemplate this situation: if we only felt happiness in the absence of all other emotions, it wouldn’t have any meaning. “Happiness is not a stand-alone feeling. Happiness is a comparative emotion.” writes Jack Schafer Ph.D in Psychology Today.

When you do difficult things or take on challenging tasks, it makes the easy feel much more enjoyable, light and fun. The harder the task and struggle, the easier—and sometimes more enjoyable—the less difficult tasks become. Drawing parallels between the binary of happiness and sadness, Jack writes,

The measure of happiness a person feels is judged against the measure of sadness a person felt in the past. The greater degree of sadness, the greater degree of happiness.

While these are of course emotions, I think we can draw a comparison between the difficult and the easy. I like to intermingle difficult reads with lighter reads simultaneously to make the process more enjoyable. When I was reading Ulysses, I was also reading the Count of Monte Cristo before bed. While the latter book is still not the easiest read, it felt a hell of a lot better in contrast to Ulysses.

A similar parallel can be drawn with working out—the tough days (ie. tempo runs, high intensity interval training or running in bad weather with challenging elements) make us appreciate the lighter and easier days so much more. Without the hard days, life can become a blur of sameness. Without the yin, there is no yang. Two extremes help define each extreme. If we read difficult often, the “easier” (even if it still isn’t that easy) feels much more like an enjoyable pastime. We garner more appreciation and gratitude for the more challenging pieces of literary work.

Framing

While “finding your why” has become trite and repetitive advice at this point, in order to uncover the motivation to not only pick up a difficult book and read it, but actively try to understand it, is going to require testing out some different approaches. If your intent is entirely ego driven (ie. adding the book as an ostentatious display on a bookshelf or as a talking point on how smart you are), then a) I can almost guarantee you’ll be miserable the entire time reading it and exert a ton of will power or b) you’ll abandon it all together. External validation does not provide prolonged motivation. 

While of course you can obtain bragging rights from forcing yourself through a ~900-page beast of a novel that makes little to no sense, a much more enjoyable mindset is propelled by curiosity. Curiosity and understanding what made this novel famous; the revolutionary ideas and the prolonged shelf life of a book are the driving forces behind getting me to pick up the book, read it, and actually invest the time to interpret and decipher the message(s) between the lines. I just genuinely want to know and am intrinsically motivated. When I pick up a text with little understanding of its synopsis, I rarely get through it and if I do, it’s by force and resentment towards the damn book.

Mid-way through Ulysses, I came up with the idea for this blog post—to share some of the strategies I learned that help me finish the novel. As I continued to progress episode by episode, I added new sections and reworked sections within this post. I developed a new form of motivation—to share my experience with others in the hopes it will help you, the reader, tackle that challenge you’ve been reluctant to pursue.

This has been the strongest frame for me, and similar to topping my glycogen stores with a gel and a sports drink at mile 20, this new idea topped up my willpower reserves to get me through the final leg of the race; crossing the finish line at episode 18. 

A few other examples of framing for me include:

• Challenge is one of my core values. Athletically and intellectually, I like to push myself into the unknown—despite how daunting it might be. If I feel fear and intimidation, I know I’m on the right path and on a trajectory for self-growth.
• Improve my writing: reading difficult texts that blend various literary styles has given me the motivation to find my own voice.
• I have a newfound passion for classic literature and for the sheer love of learning about literature across different periods in history.
• Reading difficult helps me develop more self-discipline, focus, and patience—all traits that can be harnessed in other aspects of my life.

The more I read into the unknown, the more humble I become. Instead of approaching a read thinking “I know this already,” I have to put my ego aside and open my mind to the new. “ It is impossible for a man to learn what he thinks he already knows.”, writes Epictetus.

Think through the reasoning of why you want to read a specific text. While it’s okay to want to tackle it for bragging rights or to have it under your ‘literary belt’ (so to speak), this frame will require so much willpower and self-discipline and the chances of you throwing in the towel grow substantially. So instead, think through other frames that provide you with long lasting motivation and increase your chances of success. For me, that’s challenge, competency, and curiosity. 

How to Tackle Tough Reads

Now let’s get into the tactical part of the post. While there isn’t a clear cut step-by-step guide (we all have to experiment with our own process), I encourage you to test out some of these tips before diving into to your next (or first) challenging read.

Do Some Groundwork Before Starting

Ryan Holiday recommends ruining the ending; that is, research and try to understand the book before even opening it. Ryan writes:

The first 50 pages of the book shouldn’t be a discovery process for you; you shouldn’t be wasting your time figuring out what the author is trying to say with the book. Instead, your energy needs to be spent on figuring out if [they’re] right and how you can benefit from it.

The first step is to do a bit of pre-reading. When I pick up books on philosophy, for example, I start by first reading up on the author, their theories, complimentary pieces of work, reviews and Spark Notes. I also always read the introduction which, for classic texts, is generally prefaced by another author. The intro gives more context about what the book is about, the major themes, the writing style, and any accompanying criticism (for Ulysses, there was a lot—it was even banned in certain countries for periods of time). This helps provide the reader with a more holistic view of the novel before diving into the work itself.

I followed the same protocol before picking up Ulysses. After reading through a few summaries and Wikipedia pages, most referenced the parallels between Ulysses and Homer’s The Odyssey. I decided I was going to go all in on this one so bought and read The Odyssey first as a primer (which I loved) before starting James Joyce for the second time. Ulysses also references a lot of Shakespeare, specifically Hamlet, so if you’re going to attempt this one, maybe brush up on the scripts of a few famous plays or at least the major themes throughout these works. Does it sound like you’re going back to grade 9 English class? You probably are, but this time, it’s a lot more liberating knowing it’s motivated by your own genuine curiosity, not because it’s assigned to you.

Ulysses is the Latin word for Odysseus and Joyce’s characters resemble the same characters from The Odyssey (ie. Bloom and Odysseus, Stephan Dedalus and Telemachus, Molly Bloom and Penelope, etc.) and is broken out into 18 episodes—or “chapters,” if you will. There’s also a ton of symbolism that aligns with the major episodes in The Odyssey, although this isn’t explicitly overt (Joyce’s writing is highly allusive). The introduction of Ulysses also offers the The Gibbert Schema that was provided from Joyce himself to explain the “thematic architecture” of each episode and help readers better grasp the many underlying themes the book offers. Basically, he knew his book was a tough read and wanted to offer his reader’s some support. Thanks, James.

The Process While Reading

When I felt like I understood the big picture and did what I thought was ample pre-work, I was ready to finally dive in. However, my homework didn’t end there. Before reading each episode, I would read the Spark Notes summary followed by the episode analysis. This is where I really understood the parallels and symbolism between The Odyssey and Ulysses. There is no way I would understand what was going on in each episode otherwise, which would have made the 933-page read unbearable.

If you’re tackling challenging content, pre-reading the chapter summary and analysis before reading the actual chapter makes it easier to absorb and understand, and makes for a much more interesting (and fun) experience.

Break the Book Into Digestible Chunks

Before starting this never-ending novel, I set a roadmap for myself and a goal to get it done within 2 weeks. I knew if it was going to take me any longer, I would start to lose interest and probably abandon it. Obviously, this depends on how much time you can devote per day to the task, but I don’t think you should extend reading Ulysses for longer than a month. I saw some advice out there that recommended reading one episode per week—that’s 4.5 months! 

With 18 episodes total, that rounds out to be roughly 1.3 episodes per day. Most days I tried to aim for 2 (especially on weekends) and front-loaded heavily over the first few days (even reading 3 so I could read a bit less as the weeks progressed). However, what I didn’t realize is that the first 8 episodes are much shorter than the latter half of the book, which made me have to pivot strategies. It only came to light later that this episode structuring was on purpose. Patrick Hastings writes: 

Joyce trains you in how to read his novel, beginning with challenging but rather short chapters. If you finish each episode the same day you start, you will build the momentum and confidence you need to finish the book. Joyce gradually builds your reading muscles in these manageable early episodes so that you are prepared to handle “Scylla & Charybdis,” “Oxen of the Sun,” and “Circe” later.  

Whether you assign a daily chapter goal or page count, I recommend breaking out a big text by chapter/pages and setting a plan of attack before diving in. When it comes to longer reads, the more time I take, the faster I lose interest. In my experience, it’s better to keep up the momentum for a shorter period of time than to tackle a few pages a day for months.

Look up things are you go

Even after doing all this groundwork, I still needed to revisit Wikipedia and other sources often throughout the course of my reading. There’s like a million characters in Ulysses and with new ones constantly popping up on the regular, I was revisiting the character list on Wikipedia often. This helped me not only understand who they were (ie. daughter of this person or father of that person), but their personality helped me better understand the monologue—what they were saying and their intent behind it. In the Cyclops episode for instance, I knew the character the citizen was an anti-Semitic, xenophobic, Irish nationalist that ran parallel with the Cyclops (Polyphemus) in The Odyssey.

I also looked up terms and phrases often; if I saw a specific word appear more than a few times (ie. “parapet” and the “viceregal cavalcade”), I’d do a quick Google search to understand what the term meant. However, with Joyce there are so many words that are either made up or mentioned once, you should be a bit cognizant of the time you spend doing this. If I looked up every reference, word, name or place I didn’t recognize, I’d probably be reading the novel for 10 years. 

It’s important to be patient with the process and not rush through it. If you really want to take away the most you can from each difficult read, take the time to really try to understand it the best you can.

Take (many) Breaks

For the last half of the book and as the episodes increased in difficulty, I needed to take more and more breaks. I would never go through a long stretch of pages (ie. 50-100 pages) without stepping away for a little bit. While it takes some time to warm up and really get back into the novel, as soon I start to feel my eyes glaze over the page or my mind wandering, I knew it was time to take a break. 

Get up, walk around, go to the bathroom, grab a coffee, whatever. With Ulysses, I broke it up into 2-3 stretches a day. I’d read for ~30 minutes at lunch time, ~45 minutes after work, and if I wasn’t too sleepy, I’d do another 20-30 minute session right before bed. Of course, the amount of time I could commit each day varied, but I tried to slot in my reading whenever I had some time or wanted to take a break from work.

Breaking the book up into digestible chunks kept my mind fresh and alert. Akin to building up your running mileage over time, I was slowly building up my reading endurance—allowing me to go for longer stretches in one sitting.

Be Easy on Yourself

This is probably one of the most important strategies: be easy on yourself—remember that it’s okay if you don’t understand everything right away. Even after following all of my own advice, when I read Nietzsche’s Beyond Good and Evil, I was still so lost in several parts—it’s such a different way of thinking and that can take some time to interpret and rewire your train of thought.

But as you continue reading and learning in each discipline or diving deep into a specific author, it will become easier over time. Montaigne’s Essays were much easier to understand after reading Nietzsche and Marcus Aurelius, and of course, Ryan Holiday (who makes stoicism accessible for us). I was getting acclimatized to the style of writing during various periods and started to understand some of the famous stoic references sprinkled throughout. 

Straight up even after doing all this additional work, there were still so many parts of Ulysses that I didn’t understand. I told myself that was okay though—I’m not going to absorb everything the first read and it’s okay to return and reread the book down the line (maybe in the next year or two). The point is that I did the best I could and am proud for getting through it and learning it to the best of my ability. Joyce knew that Ulysses was the kind of difficult read that would “keep the professors busy for centuries.” 

Read More in the Same Discipline

Ryan recommends choosing your next read from the bibliography of the book you just finished. He writes that, “this is how you build a knowledge base in a subject—it’s how you trace a subject back to its core.” The more you read, the better you become at rounding out your knowledge on a topic. 

Final Thoughts

Big, challenging reads can of course be intimidating, but by doing some homework beforehand and finding the right frame of mind, we can approach challenging texts with much more enthusiasm. We can garner the endurance to get through the long reads as long as we’re patient with the process and invest the time and energy to understand it. Would you read a Latin textbook if you only spoke English? No, you would learn at least some Latin first before starting. The same holds true for challenging reads: learn some of the language, the jargon, the major themes, and takeaways before diving in.

The more you do this, the easier it becomes, and the more knowledge you develop. There’s nothing more satisfying and fulfilling than developing expertise in an area that was once so foreign to you. 

The most important takeaway is this: figure out why you want to read the text before starting and feel free to test out different frames to see which one provides you with the prolonged energy and motivation to finish. It’s a reiterative process and totally okay if you don’t get it right the first time. Just be wary of external validation, social currency, or anything ego-related; it will reduce your chances of finishing successfully. 

Lastly, we should be able to pull something away from every book we read—if we don’t, it should be abandoned. I’ll leave on a word from Epictetus:  

Don’t just say you have read books. Show that through them you have learned to think better, to be a more discriminating and reflective person. Books are the training weights of the mind. They are very helpful, but it would be a bad mistake to suppose that one has made progress simply by having internalized their contents.

Good luck on your next tough read!