Reading Better
And more enjoyably!
As a forewarning: I thought this post was going to be short, but when you try to encapsulate everything you’ve learned so far on consuming content…well, it gets to be very long (in my defense, there is literally a book called How to Read a Book and this is significantly shorter and less dry).
I would think of this as a litmus test of your attention span ;) And if there’s a lot of struggle to get through it, you can either blame it on my writing style or read a later post I’ll make about re-lengthening our attention spans.
To kick off, two quotes that encapsulate my reading philosophy:
If you only read the books that everyone else is reading, you can only think what everyone else is thinking.
Haruki Murakami
Every great book is underpriced; no bad book is cheap enough.
Matthew Butterick
A quick note: for the rest of this post, I will use terms like “read” and “books” but in general I mean any type of content consumption, including audio, conversational, visual, etc.
First, let's define "successful" reading because, if our definitions differ, you can stop reading 🙂
I require both of the following:
It reveals to me insights about life or the world. What is an insight? I think IDEO captured the essence: an insight is something true but not obvious. Until after we know it, of course! The best insights, for some reason, are often obvious in retrospect—maybe because we all come with good innate intuition about what is true. Insightful does not have to mean serious, philosophical nonfiction. In fact, some of the most insightful books I've read were fiction written in the last 5 years (so not “literature”)—ones that were subtly yet deeply revelatory about the human experience and societal psyche.
It's enjoyable to read. People often ignore this criterion because they think worthwhile content has to be suffered through. However, if we suffer too often when reading, we will build an aversion to reading, which will make us default to TikTok more often (which, by the way, I have nothing against if it actually brings you joy; it often does for me—enjoyment is a worthwhile end in itself). I have made an exception to this rule only twice in the last 5 years.
Between the two, the second is more important than the first.
And to be even more precise, below are popular reasons people read that are not often mine:
People read what is trending globally or among friends for social reasons: they want to participate in the group discourse and, perhaps, to seem intelligent to their peers
People read for escape, to feel something different than what they feel now
People read to learn specific things for a specific purpose (e.g. to learn how to run agile sprints). To be clear, I read for this purpose, too, but I classify this as "reading a manual to learn how to put a bookshelf together"—it just happens to be less painful than "not reading a manual and trying to put a bookshelf together", but is otherwise not particularly enriching or enjoyable.
Okay, now that’s out of the way and you’re still here, let’s move on to the mental model shift. To read better, the key mental model shift is to go from “most things could be worth reading” to “most things are not worth reading”. Very few things have made this point to me more poignantly than this FT article (paywalled). Here is an excerpt:
In a thoughtfully planned survey for Literary Hub, writer Emily Temple plotted the number of books an average reader in the US might finish in a lifetime. She analysed trends for women and men across different age groups, and broke down the results into three categories: the average reader (about 12 books a year), the voracious reader (50 books a year) and the super reader (80 books a year). At the age of 25, even a super reader with a long life expectancy will finish a mere 4,560-4,880 books before they die.
That’s what we get: roughly 5,000 books in a lifetime, if you’re lucky.
Those books shape you, as much as even friendships and the closest relationships do. They mark you strongly because the choice of what to read is so personal, the whispering voice of authors living or dead in your ear such a private set of relationships.
Nilanjana Roy
5,000 books! Out of...
After we exclude serials, we can finally count all the books in the world. There are 129,864,880 of them. At least until Sunday.
Google, 2010
Excluding serials! And what about articles? And tweets? And…emails?
When this fact sinks in, we recognize the actual job here is to figure out what not to read as quickly as possible so we can get to the things that are worth reading.
To convert this realization to action, I suggest:
First, expand your reading time.
One popular way is to dedicate time for it daily, such as 30 min before bed. I have found this does not work for me because without changing other factors, these 30 minutes will feel like a chore. Instead, I suggest focusing on:
Only read what you enjoy. The trick here is just because today you only enjoy beach fiction doesn't mean this will be the case forever. In fact, our reading tastes are very malleable and on a shorter timeframe than most people think. One of the first things you'll notice as you're building a reading habit centered around enjoyment is, with increasing frequency, you will default want to open your book instead of default want to open Netflix. Not because you told yourself you "should". Once this starts happening, you can start introducing books that are less directly to your taste.
Read more than one book at a time. The fundamentals driving this is different books require different energy. At any one point, consider having your equivalent of a "beach read", a book that is not as gripping but doesn't require mental gymnastics, and a book that requires concentration. Then, whenever you have some free time to read, you will have an option that suits your energy level.
Make the medium a ubiquitous one. I’ve learned to like to read on my phone, but this is also because except for <5% of my apps, I have no notifications or badges turned on. I find that if you can read on your phone and not be distracted, it's the medium that is most ever-present in your life. There’s a reason why it is the most infiltrated by social media and messaging apps—products that depend on habit formation. Tactically, perhaps turn on do not disturb while reading, or even consider making your phone grayscale (Google “how to make phone grayscale”). FYI, I tried this; it’s highly effective but I also found it highly depressing to look at my phone for any reason, so discontinued it.
Second, quickly identify what is worth reading and what is not worth reading.
Reframe your reading goal for a year as: I considered 250 books, read 100, and completed 30.
Aggressively stop reading books. Especially ones that are boring. Nobody needs to suffer a genius’s poor writing. And this isn't 10th grade English anymore—you don't have to finish the book for class (and, honestly, did you, even in 10th grade English?).
A slightly more advanced version of this: identify quickly if a book is worth reading, worth skimming, or neither. If it’s worth skimming, skim it, and dive into the parts that seem higher quality. For example, I think James Clear’s Atomic Habits is hands down the best book we have right now on habit formation. I also think you can get most of the benefit by just skimming it and, no offense to James Clear, reading it doesn’t add a lot of nuance or enjoyment. By contrast, you can probably also get some general benefit just skimming Marie Kondo’s The Life-Changing Magic Of Tidying Up, but you get a lot more nuance re how to think about life by reading it and it’s very entertaining (you basically learn what obsession looks like when it starts manifesting in early childhood and that Marie Kondo is a crazy person).
A more efficient version of this: consume a lot of quotes. Consider subscribing to a newsletter of quotes (actually, James Clear has a good one—just Google it). These are literally the one or two lines that are most valuable from a piece of content. The Murakami quote I mentioned above—I ultimately did read Norwegian Wood but I really suffered through that book and by today’s standards would’ve stopped halfway. And even though I knew about that quote, I almost missed it while reading—it’s some offhand comment one character makes to another.
Older books > podcasts > newer books > long-form articles > blog entries > tweets > news. A long time ago, I decided to bias my reading towards older books. For one, there are more hurdles an author has to jump through in order to get published—most notably: an editor who has read a lot of books. Secondly, books that are still discussed many decades after their publish date indicate a timelessness of content. Basically, we want to ask ourselves: is it likely the author spent significantly more time thinking about and creating this than I am about to spend consuming it? And will this matter 5 years from now?
I know there's a fear that by reading “more stable” pieces of content, we might miss out on the newest but non-transient topics that frequently haven’t been codified into more lasting knowledge—such as web3 or the latest geopolitical shift. I have three thoughts on this:
The first is that we more often underestimate how transient (and therefore irrelevant) a topic is. Jeff Bezos applies this to business, but I believe this is even more so the case for life:
I very frequently get the question: ‘What’s going to change in the next 10 years?’ And that is a very interesting question; it’s a very common one. I almost never get the question: ‘What’s not going to change in the next 10 years?’ And I submit to you that that second question is actually the more important of the two — because you can build a…strategy around the things that are stable in time. …When you have something that you know is true, even over the long term, you can afford to put a lot of energy into it.
Jeff Bezos
The second is, I've found the best way to stay up to date on the newest topics is to find friends who are interested in staying up to date on that topic and having them send you articles/tweets 😄 To this end, it’s nice to have friends who read very differently than you do—for example, my husband has figured out how to curate Twitter for himself and mostly reads tweets. Not the only reason to keep somebody in your life but…it helps 😄
The third is, if you still insist it’s worthwhile to assess, filter, and read the content yourself, then I suggest figuring out what is the equivalent hierarchy of format. For example, if web3/blockchain is the topic, I have found academic papers > very specific podcasts > very specific newsletters > very specific Twitter accounts to be the hierarchy of formats.
A quick aside on podcasts and why they're ranked so high: for whatever reason, the format of dialogue, even recorded dialogue, really loosens tongues. Plus, there are many luminaries who would never bother to write (except maybe via ghostwriter, and even then only after they retire). In the hands of an expert interviewer, this leads to some deeply insightful content that literally would not have otherwise ever been shared. The key to finding the best podcasts is to find these expert interviewers.
Before podcasts, I think accessing this type of information required being invited to exclusive conferences and fireside chats, but luckily most of that knowledge has been democratized via podcasts.
Liberally invest time and effort to evaluate if a book is worth reading before jumping in. We spend the time researching the things we spend money on. Why do we not spend the time researching the things we spend time on? For me this looks like:
Step 1: If there's a particular topic I'm interested in, I will first go wide: I'd probably look through the first 5 pages of Google search results on, say, "best books on poverty", and build the first list of books that seem frequently repeated across lists. If no particular topic, my to-read list is updated opportunistically.
Step 2: Then, I do a quick Goodreads search—if a book is not 4 stars or more, I immediately eliminate it, even the ones that round up from 3.99. I find, empirically, >4 on Goodreads is a very strong signal that the content is meaningfully more insightful and meaningfully less painful to read than those between 3.5 and 4. And the round-up rule is because I haven’t found it worthwhile to spend the extra 20-30 minutes reading reviews for borderline books—remember, your goal is to quickly get to the right couple thousand books from literally more than 100mm.
For books that come as recommendations from others, I always ask them why they enjoyed it and what they took away from the book. And, honestly, I ignore the recommendation unless it passes the Goodreads test.
It’s good now to revisit the Haruki Murakami quote that opened this post
If you only read the books that everyone else is reading, you can only think what everyone else is thinking.
Haruki Murakami
How do you make sure you read a more interesting mix of books because, so far, all of the methods will likely lead you to the timeless blockbusters that everybody agrees is good and worth reading? And frankly, though many of those are good, there is also a disproportionate share of self-help in that set :)
Firstly, just getting to only reading timeless blockbusters is an immense first step.
Secondly, to diversify your content, I suggest diversifying your sources of content recommendations—this can mean everything from having a range of friends who are interested in very different topics to relaxing the quality requirements at the “top of your funnel” where your time investment is low. Basically, every so often look around Twitter and various media front pages. You can also think about specific topics you’re interested in (such as climate change) and do an investigation of the best content on that topic. There are plenty of 4+ Goodreads rated books on that subject, but they’re very infrequently general blockbusters.
Thirdly, I wouldn’t bother trying to find a hidden gem. You might, but it will cost you a lot of time searching. The only possible exception I can think of is if some piece of content has a unique meaning to you at a specific moment in time and you read it at that exact moment. I think this is largely luck and can’t be designed for.
Also, for the moments when it feels like this is happening, I think the bigger factor leading to this feeling is our minds can make lots of connections from unrelated things and that is the bigger driver of how uniquely valuable something feels to you at that moment than the fact that there was only that one specific piece of content that could’ve led to that feeling.
Third, re-reading something you know is great is always more valuable than reading something you suspect is not great. The best content is worth revisiting on a regular basis. This quote encapsulates that sentiment
If you have time to read one document on the topic of startup culture, you should read through the Netflix “culture deck”. If you have time for two, read through the Netflix deck twice.
Dharmesh Shah
Lastly, a quick detour on the shortcuts people use to read more: services like Blinklist that summarize books. I have tried it and it doesn't work (specifically, I read the summaries for some books I’ve already read). The analogy in my mind is that Pokemon episode (I'm told Pokemon is in again, so I hope this also panders to my middle school audience) where they find a way to make the Pokemon evolve to their next stage before they do so naturally, and Pikachu had to fight a Raichu that had undergone this process. Pikachu ended up winning because the Raichu never gained the agility skills that are typically developed in the Pikachu stage!
If you added up all the time wasted searching for shortcuts and trying to cheat the process, the hard work could have already been done by now.
James Clear
Finally, how to apply the principle of scaling this to multiple parts of our lives—I suggest segmenting the content by topic. For me, those topics are personal growth (philosophy and psychology type stuff), kids (often also philosophical and psychological…), fiction, general nonfiction, and special topics (currently financial security/economic development and Chinese fiction, but was climate change for the last 1-2 years). As you can imagine, each topic has a different ability to scale to aspects of your life.
And now, let’s zoom back out again.
There are actually two elements that help one read better: the first includes all the things this post has talked about so far—reading more, reading better, reading sustainably. The second, more invisible, and much, much more important is the ability to synthesize, integrate, and apply what we read.
The first element, we can only augment so much—even the fastest speed readers can only 7x the average reader (80 books versus 12 per year—though that amounts to 5,000 versus 750 in a lifetime), and I bet synthesis and integration suffer (I’ve read the personal account of a journalist who read 365 books a year and it sounded like a vertigo-inducing rollercoaster that you need at least another year of sensory deprivation to recover from). This is because synthesis and integration often require savoring and reflection, and savoring and reflection require time.
This is why writing this newsletter selfishly benefits me probably more than it benefits you, as much as I want it to also benefit you :)
We do not learn from experience, we learn from reflection on experience.
John Dewey
Don’t just live one year 75 times and call that a life.
Robin Sharma
The second element, however, we can get 100x better than average, probably more. And, by the way, this second element has only become more important because actually the amount of high-quality content out in the world today has increased dramatically (at one point, the only content choice we had was the Bible!). There is a lot of benefit to democratizing content creation. However, then, the problem is subtly shifting—first, you have to weed out the nonsense to get to the good stuff (what we talked about in the first half), second but increasingly important, you have to make sense of all the good stuff, which is increasing in volume and fragmenting in format.
So how do we actually get better at synthesis and integration? As the turn of phrase goes—the answer is simple but not easy: we build up the right mental scaffolding so information can be sorted, grouped, and connected efficiently (but not too efficiently! Too much efficiency here will lead to all sorts of biases, most prominently confirmation bias).
As another quick aside, I know the type of default mental organization differs, so the following analogies might be too limiting. For example, I have heard that the way to identify if you’re a J or a P in the Myers Briggs test is that if you’re a J, your mind is like a series of filing cabinets. If you’re a P, your mind is like the floor of a messy room—nobody has any idea how to find anything except you.
A poorly paraphrased example from a former professor, John Daly:
Let’s say I tell you a fact about 1970s baseball. Now, if you know a lot about baseball, you probably have a lot of scaffolding in your mind already for it—you know to put the fact about 1970s baseball in the baseball section, under 1970s, under US Major League, and so on. The more specific your scaffolding, the more likely you’ll remember it. If, by contrast, you have no scaffolding on this topic, you will forget the fact before I am even done telling you about it. There is nothing for it to hang on to.
John Daly
They’ve actually shown that when memory deterioration inevitably happens with aging, there is almost no impact on the subject areas in which the person was an expert—presumably because the expert has gotten so efficient at storing and integrating information on those subjects that the effects of memory deterioration take a long time to overcome this self-forged advantage.
I will add one more, final layer to this—yes, we should build the scaffolding for subjects we want to be able to integrate and remember more effectively. Yes, we can build the scaffolding for topics like baseball or economic development or tech startups. Or, we can focus on building the scaffolding for extremely generalizable topics that will apply to everything, including how to think about 1970s baseball.
These topics are things like: what makes people happy or miserable, what drives individual behavior, what drives group behavior, what are the truths of our physical environment, what are the truths of our biology, what are the paths systems take to reach equilibrium, and so on.
Which brings us back full circle to my intro post and an enhancement to its point on mental models—even within mental models, there are ones that scale a lot more than others.
Once we’ve practiced this enough, the facts that matter will stand out in sharp relief from the ones that do not in all the information we are exposed to, and we will see ways to apply that information in non-obvious but deeply insightful ways.
And once we have become proficient at that, we can work on the speed to go from new information to unique insight, until we can turn it around almost instantly—we and many others hear the same set of information, and, in the next breath, we can derive (accurate) conclusions that are not yet obvious to most.
And that is what will make you a better reader. Even if you only read 750 books in a lifetime.
PS—I will likely revisit this second element from a more tactical perspective, but this post is now over 3,500 words and even I’m sick of reading my own writing.
Thanks again to Shivanku for pre-reading this post. And again, let me know if you’re interested in helping read drafts :)
PPS—I’ve been told that given the current trajectory of content, this is going to be a newsletter for Silicon Valley. I have a bit of a negative reaction to that, so am thinking about layering in more whimsical content beyond just “how I can get super efficient at everything???!?” type content because I think that’s a very sad life. My next post will likely be in the whimsical camp and I’d be curious on your reactions.