The Art of Reading Hard Books
Why you should, and how to do it well.
“Good books are over your head; they would not be good for you if they were not. And books that are over your head weary you unless you can reach up to them and pull yourself up their level.” — Mortimer Adler
I’ve just finished reading The Master and His Emissary by Iain McGilchrist.
It took 10x longer than expected. What slowed me down was the numerous moments I sat back in awe at what I’d just read on the page (it’s profound—you should read it). But also the fact that it’s not an easy read. It’s certainly not something you can leisurely scan through and gain an understanding of the concepts.
And tt’s been a good reminder of the value of difficult books. There’s something you get from reading hard books that you don’t get from easy books. And that something is what I want to explore in this post.
First, we’ll look at why you should read challenging books. How they shape you, your worldview, and your mind in particular ways. Why some of the most interesting ideas come through straining your mind to understand what’s going on. And the meta-benefits that occur when pushing through difficulty (like increased capacity for focus—which is a valuable and transferable skill).
Then, we’ll look at how to choose which books to read. Why curiosity plays such a useful role, not just in choice of book but in your ability to commit to reading it despite its difficulty. How to “argue” your way into reading something. And how to use inspectional reading to quickly figure out whether you should commit to a book.
Finally, we’ll look at the practice: how to engage in the process of reading hard books. We’ll start with the obvious but often forgotten, which is that you need distraction-free space and time. Then we’ll move on to other tactics, such as letting curiosity guide depth of understanding, using external assistance, and the power of externalization and its role in understanding.
Let’s jump in.
Why you should read hard books
In a world that fractures your attention and pushes you toward the urgent, why read? More specifically, why read books that are difficult and take up a lot of your time?
Challenging books shape you in ways that easy books don’t
There’s a qualitative difference between pushing your way through a difficult book that interests you—really stretching your mind to comprehend it—and blitzing through the latest pop psych or self-help bestseller.
It’s not that pop psych or self-help books are bad. They can have a significant impact on you. But most of the time, they don’t. You read them. You feel good in the moment. You pick up a few fun facts. And then you forget about it all while moving on to the next one.
Hard books demand something of you, but they also reward you. They shape your mind, your worldview, your philosophy. In requiring depth and understanding, they also produce it.
It’s not that easy books can’t do this. It’s that by nature of them being easy reads, they demand less attention from you. When you’re talking to a friend in a noisy cafe, you’re required to focus and direct your attention with more effort, and you end up listening better than if you weren’t required to do so. Hard books are similar. They demand directed attention, producing a sort of mental energy, which in turn leads to better understanding, depth, and comprehension.
You can skim through a book like Atomic Habits and pick up a lot of information (it’s a great book, so no judgment here). But skimming through The Master & His Emissary might give you some idea of what’s going on, but you’ll miss out on so much context that you won’t really gain understanding of the complex ideas.
I also think that when something requires less effort and attention from you, you tend not to value it as much. What’s easily gained is easily lost. I can’t tell you how many mainstream, podcast books I’ve read that have exited my brain as soon as they’ve entered. Whereas the ideas that have truly stuck with me are ideas I’ve had to wrestle with, look at from all angles, ponder, and synthesize. What is earned the hard way feels, and perhaps fundamentally is, more valuable.
As such, the attention required and higher perceived (or real) value has an impact on you, your being, and your mind. I don’t think you can truly read a book like McLuhan’s Understanding Media (I found it to be a challenging read), or McGilchrist’s The Master & His Emissary or The Matter With Things, and come away unchanged. And yes, that’s partly (maybe mostly) because they’re great books with interesting, well-structured ideas—but I also think it’s because you can’t just blitz through them. They require mental work from you.
But what about hard books that aren’t considered good/great/well-written books?
Simply don’t read them. Sure, there’s value in doing hard things for the sake of doing hard things as mentioned. You might get some benefit by reading shitty, hard books—such as the ability to withstand boredom and pain. But there are too many great, challenging books out there that it’s extremely difficult to justify reading low-quality stuff.
Some of the most interesting ideas are in hard books
Back to McGilchrist’s work, because it’s top of mind for me. While his books aren’t underground, they will never be as popular as an Atomic Habits or other hot bestseller, simply because they are more challenging to read and the topics contained in them have a smaller audience.
Due to the limits of language, some ideas simply cannot be presented in easy-to-understand writing. Some ideas, like the interplay between left & right brain hemispheres and their effects on culture, cannot be boiled down to a simple paragraph or sentence without losing important detail.
So it’s not just that interesting ideas exist in hard books, it’s that to gain a high-res understanding of those ideas requires you to venture through difficulty and complexity first. Take the following sentence, which is my attempt to simplify an idea in The Master & His Emissary:
“The right-brain is the master, but the left-brain thinks it is. This is the source of your disconnection, your lack of coherence, and a great deal of your problems.”
If you’ve read the book, then that simplification will mean more to you than it does to someone who hasn’t read the book. You’ve gone through the complexity, you’ve wrestled with the ideas, you’ve gained an understanding that allows you to read the above sentence and actually know what it means (or have a more accurate knowledge of what it means).
This is also why book summaries are only so useful. Without the contextual scaffolding, ideas quickly lose their potency. There’s no free lunch when it comes to developing understanding. No shortcut. You have to read. You have to do the work.
You learn how to focus
It’s not just that people don’t read hard books anymore, they don’t read books at all. The decline in reading is significant, and with it, the decline in the average person’s ability to focus.
In an age of distraction, being able to sit down for an hour or two and deeply concentrate on one thing is a skill. And it’s a skill that’s in short supply.
Reading hard books helps you develop this skill, because really, there’s no other way to read hard books. Good luck trying to read something difficult while your phone is buzzing, or you take breaks every 5 mins to check X or Instagram, or your TV is playing in the background.
Developing this skill opens the world up, because focus is a force multiplier. If you can sit down and push yourself through challenging texts, then you can likely push yourself through other intellectual types of work (you should frame reading hard books as work, by the way—it will help reduce the tension you feel around reading and its perceived trade-offs compared to other activities).
How to choose what to read (and commit)
There are plenty of challenging books out there to read, so how do you choose?
I think the choice you make is important. I can’t tell you how many times I’ve picked up a hard book without any motivation other than the fact that someone’s recommended it to me, and quit within the first hour of reading.
But I can tell you the times I’ve intentionally chosen to read a hard book and stuck with it despite it being a struggle (and sometimes boring). Those times have three things in common: curiosity about the topic, a reason for reading (or multiple), and a rough idea of what I’m getting myself into.
Follow curiosity
I believe curiosity is its own form of wisdom. To ignore it is stupid. It’s telling you something that you can’t quite externalize but need to explore.
Curiosity makes reading hard books enjoyable, because you want to gain understanding. The funny thing is, as you read more, you often become more curious about everything, so it opens up your world in that way.
Still, there are topics you’re likely curious about and will push through boring & hard bits to learn more about them. And there are topics you aren’t curious about (or aren’t curious enough about) where you won’t do that.
For example, I can read about psychology, neuroscience, human performance, and business all day long. That’s the world I live in. The intersection of these topics helps me in my business, helps me be a better coach, and helps me understand myself.
But I really struggle to push my way through dry, academic philosophy. Especially that which seemingly lacks practicality. Some people love that stuff. Some people are curious about it. I’m not.
Curiosity leads to commitment. And commitment is what you need if you’re going to read a hard book.
Read based on reason and outcomes
One of the things that drew me to slowly, deeply reading The Master and His Emissary was not just that I was curious about the topic, but also because I was confident it would help me personally as well as the clients I work with.
In other words, it had an immediate reward, in that it satiated my curiosity, but would likely lead to other rewards too: better coaching ability, a reshaping of my worldview, a deeper understanding of myself and others, and so on.
If curiosity is the emotional driver to read something challenging, reason is the more rational driver. And it’s something you can rely on when you feel like abandoning the book.
So, when choosing a book, it’s useful to ask:
What are the direct outcomes?
What are the indirect, “meta” outcomes that I get from reading this?
Why do I think it’s worth weeks and months of my time?
You likely do this naturally and intuitively anyway, but it can be worth externalizing if you’re struggling to decide between two or more options.
Inspectional reading/scanning
It’s hard to fully commit to a book until you have an idea of what it’s about. A brief scan and inspectional read can give you a good idea of how relevant and useful (and difficult) the book will be.
If I know a book is going to be a long read, I’ll look through the table of contents, skim through a few chapters and read some passages to get an idea of what I’m venturing into. In many cases, this leads me to choosing something else, like the time where I bought a game theory textbook, skimmed through it, and realized my math wasn’t up to scratch and there was simply no way I was going to be able to get through it given my current level of knowledge. It would have been better to not buy that book in the first place, but I have a heuristic I use when buying books: yes.
How to read hard books
Create space & time (without distraction)
Reading is a serious task and should be treated as such. It is an active, not passive task.
You will not get through hard books if they’re on your nightstand, and you also won’t get through them if you can’t carve out time and space to concentrate free of distraction.
Your ability to elicit meaning from a difficult text requires immense mental resources. And if you’re always context-switching due to external distractions, or you’re grabbing for your phone as soon as you get stuck at a hard passage, then you’ll fail to read and understand. You’ll end up “reading” 5 pages and then failing to remember anything. Your eyes travelled across the page but the words never entered your mind.
Mental energy. Space. Time.
Figure out how to use them. For me, I read late afternoon, usually outside if it’s good weather, or in my office. If it’s noisy, I’ll wear headphones. And I commit to a minimum timeframe (just like I would if I were working on a task), because I know that hard books generate resistance and without committing to a time period, I’ll have a tendency to give up prematurely.
Let curiosity guide your depth
Adler, in How to Read a Book suggests that you should read hard books fast, knowing that you won’t understand everything. This advice is worth heeding, but I take a modified approach.
First, trying to understand everything in a difficult book is an inefficient approach because:
You can’t
Even if you could it would take you forever
You don’t really care to understand everything anyway
My approach is to let curiosity dictate how deep or shallow I go. In the case of reading The Master & His Emissary, there are some parts that, for whatever reason, I have to pause and try to understand more deeply (and will bring in assistance—more on that soon). There are other parts that I’m content with not understanding. Some of the brain chemistry stuff goes over my head, but I’m fine with that because I don’t need to understand it to get the arguments and ideas.
Letting curiosity drive depth is something you’d likely do anyway if you weren’t so analytical and systematic. It’s also why I think goals like “25 pages a day” are stupid, because sometimes, a page takes 15 mins because it’s so profound and you need to research terms, reflect, re-read, and so on. Just relax. Let the book dictate the terms.
Assistance
Often, you’ll come across something you don’t fully understand, but it’s something that feels crucial to the rest of the book. If you don’t understand it, what follows will be hard to contextualize or make sense of.
What you shouldn’t do is open your phone and search Google or ask AI straight away. There is value in wrestling with the text and trying to understand it by yourself first. And if you always grasp for external help every time you encounter such struggle, you will atrophy that part of your brain.
But after you’ve wrestled with it a bit, you might still need help. This is where assistance comes in. It might be another related book that gives you the prerequisite understanding, a simple google search to understand a term, a YouTube video explaining the concept in a visual format, or similar.
95% of the time, I seek assistance via ChatGPT Advanced Voice Mode. While having my phone nearby does make me more prone to distraction, I find being able to simply ask it questions while I’m reading (without even looking up from the page) is incredibly helpful. Here’s a video from Dan Shipper showing how powerful this can be:
Talk, write, externalize.
Externalization is a powerful way to strengthen retention. It’s one of the reasons why I’m writing this article (to solidify and strengthen ideas from some books I’ve read). And it’s the same reason I make YouTube videos.
How you externalize is up to you, but I recommend at least some form of writing—even if it’s taking your own notes (keyword: your own - make them original). Writing forces you to synthesize, consolidate, and simplify.
If you have accommodating friends, you can also talk about what you’re reading. (Shout out to my wife for patiently listening to me ramble on about various topics).
Now go. Read and compound your knowledge.