how to read difficult books

advice from a self-proclaimed strong and avid reader

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 book shopper and buy only one. I ended up purchasing Thinking, Fast and Slow by Daniel Kahneman, a roughly 500-page book on behavioural economics. I had no background in the subject, but I gave it a shot anyway. It wasn’t beginner-friendly — dense with research and terminology that was complex to me — but I pushed through.

At first, I gave it a bad rating, largely because I found it difficult to read (and therefore, enjoy). Later, after reading more books on behavioural economics, I returned to Thinking, Fast & Slow and was able to appreciate the book more (this was before a good chunk of the book was debunked). I realized that many of the main ideas from the book initially went over my head because I didn’t have adequate knowledge or skills to read it thoroughly. It wasn’t the book that was bad; it was the way I read the book that was.

Reading hard books eventually became easier: I’d dive headfirst into a new subject, reading and researching intently until I fully understood what I had just read. I went from reading behavioural economics to neuroscience, then to quantum physics, philosophy, politics, history, classical literature, and economics. Each new subject came with a steep learning curve. Still, as I became a stronger reader, I began developing a methodical process to help me approach and understand difficult books.

If you, like me, enjoy reading books that challenge you intellectually but at times worry whether or not you’ll be able to keep up with the readings, here are some tips and tricks I’ve used over the years to help me read difficult books.

Read multiple times

I’ve previously mentioned the benefits of rereading a book as a writer, but this advice applies to everyone.

If you’re reading a difficult book, it’s not meant to be read just once. Challenging books are meant to be studied, and that means engaging with them multiple times to develop a deep, comprehensive understanding. Reading a book two or three times (depending on its complexity) can significantly improve your retention and understanding of its ideas.

How to read a book more than once:

• Reading Session 1: Just read. Don’t overanalyze. Highlight or underline anything that stands out or interests you. Use sticky tabs to mark the highlights.

  • This is the priming session. I don’t focus too much on dissecting the work just yet. I prepare my mind to increase exposure and familiarity with the ideas so that I can be more critical in the second reading session.

• Reading Session 2: Use annotations to dissect your highlights and each paragraph. Analyze how the ideas connect and what the author is trying to communicate.

  • During this stage, I use marginalia, which is essentially annotating in the margins. I typically paraphrase key ideas and draw connections there. Occasionally, I will also write counterarguments.

• Reading Session 3 (Optional): If you still find the text unclear, do some extra research and revisit it again with fresh context and understanding.

  • I enjoy watching YouTube videos, documentaries, or podcasts when I have difficulty reading the content. Sometimes it’s not the content itself, but the method of consumption that makes it challenging to understand.

After I finish reading the book, I like to write a 1-2 page summary of what I’ve just read, focusing only on the key ideas. This is technically when my third reading session happens, but this time I’m relying on my annotations and sticky tabs to guide me instead of reading from start to finish.

Do your research

Before diving into a book, I like to learn a bit about the author and their body of work because it helps me understand how they write and gain context for what I’m reading. Your research approach should differ slightly depending on whether you’re reading fiction or nonfiction. Some things I look out for:

For Nonfiction:

• Learn about the author’s political, social, or religious affiliations to better identify potential biases

• Familiarize yourself with key terms and foundational concepts in the field

  • Example: having a general understanding of neuroplasticity when reading about neuroscience

• Look up any additional essays or articles by the author to get a feel for their writing style and perspective

For Fiction:

• Understand the social context

  • Example: Crime & Punishment: Russian literature often includes multiple naming conventions, which provide the reader insight into the relationships between characters

• Learn the historical context

  • Example: The Great Gatsby: set in the 1920s during the era of bootlegging and excess. Knowing this helps you better analyze its characters, themes, and plot.

• Look up any additional essays or articles by the author to get a feel for their writing style and perspective.

While reading, I often write notes about ideas or concepts I want to explore further. After finishing a chapter or the entire book, I research those topics. I highly recommend keeping a pen and journal nearby to help you keep track of what you want to research and jot down what you’ve learned.

Write about what you’ve read

I’m a big advocate of using writing as a tool for learning. While I’ve previously written extensively on this subject, here are a few key reasons why writing about difficult books helps:

• It improves retention — you’re reinforcing the material and internalizing the ideas.

• It reveals knowledge gaps — trying to explain or connect ideas shows you what you truly understand and what you don’t.

• It inspires others — sharing your thoughts might encourage someone else to engage with the material or start writing themselves.

After I’ve read the books, annotated them, and written a 1-2 page summary, I like to take it one step further by composing a book review or summary that discusses what I just read.

I used to share my findings on Goodreads and Instagram, and at one point on my old blog, but now I share them here on Substack. Of course, if you’re not comfortable sharing your writing, you don’t have to. However, I suggest that you at least try to connect the information through writing.

Slow Down

Don’t rush. Especially with challenging books, take your time. Read slowly, page by page, paragraph by paragraph. Let the words sink in. Absorb the ideas. Fully immerse yourself in what the author is trying to say.

Too often, people skim through difficult books, get frustrated, and give up. But slowing down can make the reading process more rewarding and meaningful.

Remember, it’s not about how much you read, but how well you read.

Don’t Feel Stupid

Yes, difficult books are difficult — but that doesn’t mean you’re not smart enough to read them. The purpose of reading is to grow intellectually, which means occasionally reading books out of your current domain of knowledge.

At first, you might question your intelligence or feel overwhelmed. I’m here to tell you: don’t. Think of the brain like a muscle; when you first challenge it, it may feel weak, but with consistent effort, it grows stronger. That’s how you become a better reader and thinker.

Even the brightest experts didn’t start out as experts. They developed their knowledge slowly, step by step. You may feel “stupid” while reading something difficult, but you’re actually becoming smarter through the process (kind of like how lifting a heavy weight makes you stronger over time).

So if you’re planning to read some challenging books this year, give yourself some grace, take your time, engage deeply, and don’t complicate or rush the experience. Reading should be both enjoyable and intellectually stimulating — allow yourself to be challenged, and enjoy the process!

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Hi, I’m Rana!

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Rana