10 Techniques I Use to Make Reading Classic Books More Enjoyable  

In high school I was often bored by the classics we were assigned.

Now I relish the time I get to spend with Dickens, Austen, Wright, or Plato. 

What changed?

Well, I got older, and the classics, with their heavy topics and complex characters, are really meant for adults. Plus, it was my decision to read them, not a teacher’s, and so I took to it more passionately. 

But aside from that, I started approaching classic literature differently, and became a better reader. 

Today I’ll cover 10 techniques that’ll make reading the classics more enjoyable for you, while also improving your classic reading skills. 

Because what we’re good at, we tend to enjoy. 

Pick the Right Classic Book for Your Interests

If you were selecting a modern novel or non-fiction book you’d pick one that fits your interests. 

Do the same when selecting a classic. 

While classics deal with existential themes and are thus universally relatable, some will still be more interesting to you than others. 

And some classic books will feel like a slog no matter what techniques you use. 

So, if you’re interested in romance, consider an Austen novel.

Self-education and autodidactism? Can’t go wrong with Martin Eden. 

War? A Farewell to Arms and All Quiet on the Western Front are great places to start. 

Once you’ve identified a few interest areas, hop on Google and search “classic books about X” and you’ll find plenty that’ll pique your interest. 

Go Somewhere Fun to Read the Book 

The other day in an interview for a staff writing role I was asked “how do you handle new writing assignments that are thrown on your plate last minute?” 

After shuttering at the thought, I collected myself and told her what I usually do in such cases. 

I pick up my laptop, hop in the car, and drive somewhere different, some place I rarely go. 

This could be a cafe, a library, a park bench, or a restaurant. I find that a new environment creates a sense of novelty that electrifies my curiosity-gland. 

The outside world puts me in a higher state of arousal, like a dog on a walk.

But it’s not only me this happens to. 

A study in neuroscience discovered that daily variability in physical location is associated with increased mood (positive affect) in people.

I use this same approach when I’m not in the mood for reading a classic book. 

I’ll grab my book and hit a cafe. 

Sitting there sipping my coffee, I often find my attitude towards reading has changed. I’m excited to tackle it. 

And I’m able to read for longer and enjoy the book more than if I had stayed at home. 

Try it out. You might just find that the new environment stimulates your mind and keeps you from getting bored. 

Change Your Expectations

A lot of the time the root cause of your boredom is mismatched expectations. 

We hear about this happening in the bedroom. 

A man watches so much pornography that he is let down by every real sexual experience he has. 

He’s so focused on how the sex isn’t as wild as the stuff he watches that he’s totally blinded from the intensely satisfying intimacy that is right there in front of him if only he’d stop trying to make it match his skewed vision of how sex should be and focus on the moment. 

It happens when you watch movies, too. 

Recently I sat down to watch My Dinner With Andre, a movie that takes place over dinner between two men. It’s 2 hours of dialogue, almost no action whatsoever. 

Fortunately, I was expecting to listen to engaging dialogue about difficult, philosophical topics, so I deeply enjoyed it. There was not a dull moment. 

If I had expected to have the same experience I got from watching Interstellar, I would’ve been disappointed. 

And that disappointment would’ve been all encompassing, ruining my ability to appreciate the film for what it is, a literary think piece. 

This same thing happens a lot when people who are used to some fast-paced or easy-to-understand books try to read classic books. 

They come to the book expecting thrills, shocks, and simple language. And when they realize this is not going to provide that experience, they get annoyed and bored. 

The remedy is simple. You must change your expectations. 

Although some classics will be a wild ride for you full of dopamine hits, many of them will be much slower paced, so pick another reason for reading the book. 

Do some research and figure out what the book is known for and what it is about. 

For example, one could read To Kill a Mockingbird to learn about racial injustice that took place in Great Depression America. Their expectations would surely be met, and they would thus enjoy it more. 

A thriller reader would benefit from going into Moby Dick hoping to encounter some of the most sublime uses of the English Language to date. 

A self-help enthusiast should pick up Aristotle’s Nicomachean Ethics hoping not for practical advice like “meditate 10 minutes per day”, but for nuanced food for thought about how to live a good life. 

If you’re suffering from mismatched expectations, this simple tweak should help you find more enjoyment from the books, appreciating them for what they are rather than focusing on what you wish them to be. 

Side Note: The source of your boredom might be one of these 8 common hurdles for new readers of the classics. Check out the article to find some solutions.

Slow Down (Stop & Smell the Roses)

Transcendentalist writer Henry David Thoreau once wrote, 

“Books must be read as deliberately and reservedly as they were written.”

While that might be a bit of a stretch for most of us with real jobs who don’t live in a cabin on a lake, there is still some practical advice in that statement. 

When reading the classics, your enjoyment is often inversely related to the speed at which you read the book. 

The faster you go, the less gems of language and insight you’ll notice. 

When you slow down, you start to see more of the beauty and get more of the benefits of reading classic literature, such as deep reflection on ideas and characters, transportation into other worlds, and meditations on your own life. 

Here are four ways to slow down your reading and get more out of the classic:

  • Collect Your Favorite Passages: Stop and write down your favorite sentences and passages in a literary commonplace book (a journal where you collect literary beauty, truth, and wisdom). Also, ask yourself why you captured it. This will help you better understand yourself, your tastes, and your interests. 
  • Write in the Margins: Get into a conversation with the writer by actually writing your thoughts in the margins. Or note patterns, themes, and ideas that stick out to you. This will make you become more invested in the reading and less bored. 
  • Seek to Draw Connections to Your Life: Be an active reader and try to tie the events or characters in the story to the happenings and people in your real life. This will make the classic feel more relatable. For instance, you could ask yourself “I wonder how my grandpa handled losing friends in battle. Did he react like this protagonist is?”  

It’s counterintuitive, but habits like this that slow you down will actually lead to less boredom when reading classics. 

Check out my guide to deep reading classic novels if you want to learn more about this reading strategy and how it can enhance your classic reading experience, while also helping you retain more of what you read. 

Gain Knowledge in the Other Liberal Arts

Sometimes, knowledge of other subjects can enhance your understanding, and thus appreciation, of classic works of fiction. 

For example, self-learning the basics of psychology can make the characters you encounter all the more fun to analyze and think about. They become patients you can practice on. 

History is another good example. When you read about the area in which the story takes place, you’ll catch more of the references and better understand the reasoning behind otherwise confusing character behavior. 

You’ll learn that they’re not crazy, but that the social mores of the time and place compelled them to do such a thing. 

In my research for this article, I came across this excellent advice from redditor Gene Endress:

“In my experience, every “liberal art” is enhanced by experience with the other liberal arts. So, if you want to enjoy literature, then your experience will be greatly enhanced if you also have some knowledge of history, philosophy, psychology, sociology, politics, rhetoric etc., and the more the better. (Similarly, a knowledge of literature enhances understanding and appreciation of all those other disciplines too.)”

If you want to become somewhat of a polymath, and reap the benefits of interdisciplinary knowledge, check out my guide on how to give yourself a well-rounded education, where I share my 4-pronged approach to lifelong learning and other principles of gaining breadth and depth.  

Learn About How Literature Works 

I say this a lot on the blog: we tend to appreciate what we understand. 

The other day I had to replace a headlight bulb in my Subaru. At first I was annoyed at the inconvenience. 

But while watching YouTube videos on how to replace the bulb, and other on how the car’s electrical system works, I started to appreciate the car on a deeper level, and the chore went from confusing and boring to interesting and satisfying.

Something similar happens with classic books when you take the time to learn more about literature

With knowledge of the component parts and the millions of choices the author made to put them together, you become like an architect admiring a beautiful home. 

There are many ways to learn more about literature, from reading literary criticism to grabbing a basic introductory textbook on the subject. 

You can also do things like read or watch book summaries and analyses after finishing a classic. These will give you a better critical vocabulary for thinking about the work you read next. 

I also have a 14-book reading curriculum for beginners self-studying literature. This should give you a firm foundation in the subject.   

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Find a Reading Buddy

Consider getting a reading buddy. You can both read the same book and then talk about it together once every week or two. 

 It doesn’t even have to be formal. The friend doesn’t even have to read the same book. 

Even just having a friend who is open to discussing books and ideas with you is often enough to help you see the benefits of reading classics. 

For example, last night I had a Zoom call with a friend and I was telling him about Beyond Good and Evil and Nietzsche’s concept of slave morality, which, to my surprise, I was actually able to explain pretty well.

He was intrigued and wanted to keep discussing it. 

This evidence that your reading is paying off motivates you to do more of it.

Read more about the benefits of having a reading buddy here in my article The Value of a Reading Buddy for Self-Education.  

Get Comfortable Giving up on Books 

One of the best ways to avoid boredom while reading classic books is to stop reading the books that cause this tremendous boredom. 

That doesn’t mean to give up whenever a book gives you trouble. 

Pretty much every classic I read gives me at least a few phases of boredom, either because the material wasn’t resonating with me or because I was in a hard-to-impress mood at that time of reading. 

So do try to push through those periods. The final step in the stairway of boredom might be ten steps away, and there might be a waterslide attached to it, for all you know. 

That said, if you’ve read 80-100 pages of the classic and have felt the whole time like you’re traversing sand dune after sand dune without more than a few sips of beauty or joy, then it might be time to surrender and come back to the book another time in your life. 

Maybe in a year, maybe in ten years, with experience at your back, the book will be more relatable and interesting to you. 

And when you do give up, don’t feel guilty. The author is likely dead anyway. Plus, the author probably gave up on dozens of classics in their lifetime, too. 

Time is valuable. So don’t let your idea of yourself being a person who finishes things drive you to never drop books. 

Trapped with this book you don’t want to read, you’ll end up going months without reading at all. 

When you could read 20 pages of a book you enjoy, instead you’ll watch tv and feel ashamed for not reading the book you’re a prisoner to. 

Grab a Drink

Ernest Hemingway famously said “​​I drink to make other people more interesting.”

Sometimes — only sometimes — I drink to make the classic novel I’m reading more interesting.

I use this technique only when I’m extremely fatigued from the day and feel that strong pull from easier pleasures — Netflix, YouTube, mindless scrolling. 

I did it with Hemingway’s Farewell to Arms a few times (as the serious drinker he was, I think he’d approve). 

I find that a cold beer or a glass of red wine makes cranky, spiritless me more receptive to the charms of storytelling, wisdom, and beautiful writing. 

While it shouldn’t be your go-to technique, grabbing a drink can help you get in the reading zone when you’re in an especially unimaginative and lazy mood. 

If you’re trying to cut back, coffee or tea can also have a similar effect. So can a cup of apple juice. 

Whatever it is, a drink enhances the reading experience much like popcorn enhances the moviegoing experience. 

One Last Thing: Change Your Relationship With Boredom

Boredom is something we tend to avoid at all costs these days. People want constant, instant gratification from their entertainment. They want dopamine hits now, not later, and they don’t want to work for it. 

Unless you’re a pro reader, reading classics doesn’t offer that machine-gun of pleasure to your frontal lobe. 

There will be times when you’re bored. There are still times when I’m bored.

But I continue on, knowing that these five minutes of boredom will likely lead me to an eye-opening revelation or an intense tear-jerking scene. 

Reading the classics requires something from you. It’s not passive entertainment. And, because of that, you grow as a thinker and person each time you do it. 

Plus, the more you do it, the less boring it is, because you just get better at it. Surfing was boring when I sucked. Now that I can stand up it’s way more fun. 

So think of boredom as something that’s inevitable in reading, but that will subside as you progress as a reader or just reach the next chapter. 

Want to get into classic literature but aren’t sure how? 

Grab my 14-book program for breaking into the subject. Inside you’ll find 4 types of books that helped me self-learn the basics of literature. 

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After graduating college with an econ degree I realized I was still anything but well-educated. Over the last 4 years, I've been trying to fix that, autodidact-mode — by reading books and engaging in self-directed study across multiple subjects. On this blog, my goal is to share my learnings and help others get a well-rounded education outside of school. Education, after all, is a lifelong process, one well worth the investment.

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