How I Choose What To Read

“Reading books is the real-life version of collecting mushrooms in Super Mario.” — Some random guy on Twitter

Reading is a cheat code. Improving what you consume is the fastest way to accelerate your pace of progress. 

Time is scarce, so you can’t read everything. You have to make tradeoffs. As you choose what to read, you walk a balance between thinking differently and knowing more than others. 

Read an enormous amount of books. More than you think you need to, not the ones that everyone else is reading, and ideally covering a wide range of topics. Informational edge is found in obscure, hard-to-digest sources. Get comfortable with weird parts of the internet.

Domain expertise is great, but you also want to build a breadth of knowledge. That way, you can identify patterns and sense emerging trends.

If you have the means, pay for the content you consume. 

Even better if it’s a subscription, where the creator is optimizing for lifetime value. That way, you know their incentives are aligned with yours. The logic of the business model dictates the content. Most ad-based content is optimized for clicks, and most paid content advertises for engagement. Ad-supported content is fine, but don’t make it your default. Attention is too valuable to waste time on most free content.

Building a Habit

Reading is a way of life. A great book will stretch and strengthen your mind — an experience that’s taxing as it unfolds, but fulfilling in retrospect. 

Most of us don’t devote enough attention to accelerating our learning. In fact, most people expect learning to decelerate over time. School kills our innate curiosity. After college, people lose interest in self-improvement. 

Voracious learning requires consistent focus and discipline. Reading is rarely the easy choice. The modern world is filled with distraction, superficial entertainment, and demands on our attention. This makes deep reading difficult, even though the benefits of doing so are immense and compound over time. 

Read, Read, Then Read Some More

“You could try to pound your head against the wall and think of original ideas or you can cheat by reading them in books.” – Patrick Collison

Read a lot.

When you first begin your reading habit, it’s best to focus on having fun. Cultivating a habit is hard. The best way to stick with it is to have fun with it. Resist the temptation to finish every book you start and discard bad books as soon as possible. It always feels wrong, but that’s okay. 

Once reading becomes a habit, people automatically navigate towards more productive reading. As their knowledge grows, they refine their tastes. 

However, there’s an even faster way to improve the quality of what you read: start writing publicly. Feedback loops and forcing functions are powerful self-improvement tools. Open your ideas to public critique and the quality of your inputs will improve. 

My reading is driven by five goals: 

  1. Enjoy learning

  2. Improve my writing

  3. Appreciate the world

  4. Earn respect from my peers

  5. Develop a well-rooted worldview

Based on these values, I developed five reading heuristics.

Reading Heuristics

1. Trust Recommendations — But Not Too Much

While most people will recommend new books, old books that’ve stood the test of time are likely the best use of your attention.  To be sure, there are exceptions to this. Depending on what line of work you’re in, there are must-read, “cannon books.” Those are probably worth your time

I try not to look for the best books. Instead, I hunt for forgotten old books and under-valued new ones. Crucially, this heuristic guides me towards ideas that nobody is talking about. 

When I interview or meet somebody I admire, I always ask for book recommendations. 

Don’t trust what everybody in society is reading. Trust what the people you respect are reading instead. Find people whose recommendations you trust and read what they recommend. 

2. Tame the Thrillers

Seek thoughtful, opposing views from thoughtful people whose thought processes you respect. 

Read books that the ideal version of yourself (in 20 years) would have been proud to have read. If you’re reading challenging or intimidating books, you’re probably on the right track. Reading the right books is challenging and uncomfortable. 

Strive to relish this challenge. Always ask: Am I actually progressing or is this source giving me the illusion of progress?

As a kid, I was always scared of upside-down roller coaster rides. But after I went on my first one, I realized how much I missed by choosing the easy rides instead. The up-side down roller coasters are the most memorable rides at almost any theme park. A little bit of challenge up-front leads to large, long-term rewards. Tame the thrillers. You won’t regret it. 

3. Blend a Bizarre Bowl

Arthur Schopenhauer once said: “The task is not so much to see what no one has yet seen, but to think what nobody yet has thought about that which everybody sees.” 

It’s usually better to attack a subject from all sides than to attack it directly. Read in clusters. For example, I’ve been learning about the history of New York. Instead of reading a book directly about “The History of New York,” I’ve explored the Art Deco art movement, influential New York City political figures, the history of St. Marks Place, financial history, and New York City architecture. 

Read books that intimidate you. Have a bias for books that would push most people away. These books are either too long, too difficult, or too counter-intuitive, but they will likely contain information that will give you an edge and spew out interesting, unexpected ideas.

As Eugene Wei wrote: 

“You can try to improve how much you learn from each book, but probably the greatest gains from selecting the right set of books to read. Those books are likely older than the ones that are really popular today.”

One problem: there are so many options. This makes selection difficult. 304,912 books were published or re-published in the United States in 2013. There are immense benefits to choosing the right book. The right book at the right time will re-thread the tapestry of your psyche. 

Seek diversity in your reading life. New ideas come from the weird juxtaposition of ideas. If you’re reading this, you’ve already won the lottery. Whether you’re on your phone or your computer, you have access to more computing power than all of NASA had during the Apollo days, when they sent a man to the moon. Through the internet, the vast majority of human knowledge rests right in your fingertips. 

If you leverage the internet properly, you’ll be exposed to a bizarre blend of ideas from all corners of humanity. As a general rule, Informational edge is found in obscure, hard-to-digest sources. It’s the weird books that will change you. 

Connecting insights across time and space will spark fresh ideas. As Rene Descartes wrote: 

“The reading of all good books is like a conversation with the finest minds of past centuries.”

Connecting insights across time and space will spark fresh ideas.

On the internet, you can connect with ideas from all corners of the world, from the pyramids of Giza, to the temples of Athens, to the skyscrapers of New York. Diversity helps. 

Here’s an example: Right now, I’m reading a book about Austrian Economics, the history of art from ancient times to the modern era, a collection of essays on the role of media throughout history, urban politics in New York City, and another on how music works. 

If you’re reading a book published in the past 50 years, listen to interviews with the author while you read the book. YouTube is the best school in the world. It’s like a coffee shop with direct, right-into-your-ear access to the world’s smartest people. It will improve comprehension and give you a stronger connection with the writer.

Over time, you’ll blend a bizarre bowl of ideas and develop a unique and interesting worldview.

4. Trust the Lindy Effect

The Lindy Effect says that the future life expectancy of non-perishable things like books is proportional to their current age. As Nassim Taleb once wrote: 

“If a book has been in print for forty years, I can expect it to be in print for another forty years. But, and that is the main difference, if it survives another decade, then it will be expected to be in print another fifty years. This, simply, as a rule, tells you why things that have been around for a long time are not “aging” like persons, but “aging” in reverse. Every year that passes without extinction doubles the additional life expectancy.”

If you read what everybody else is reading, you’ll think what everybody else is thinking. Have a bias for books that would push most people away, especially if they are still in print after many years. These books are either too long, too difficult, or too counter-intuitive, but they will likely contain information that will give you an edge.

I must admit, this isn’t always the case. Many old books are wordy and verbose, which makes them annoying to read. That’s okay. Remember, these are general rules. Most of my favorite books were written 10 – 70 years ago. 

The media is paid to get your attention. Recently, a reporter for a major news magazine said her success depends solely on page views. Sometimes, she writes seven articles per day. In her words: “My job is to write faster than I can think.” And yet, her average article is read by more than 500,000 people.

We’re stuck in a violent and continuous storm of news. The vast majority of news has no informational value. It’s entertainment, with a veneer of importance. 

As Naval Ravikant observed: 

“The Internet commoditized the distribution of facts. The “news” media responded by pivoting wholesale into opinions and entertainment.”

Avoid 99% of the news. If the news is significant, the information will find you. Don’t believe me? Try reading last year’s newspaper. If you do read news, read old news. 

Time is like a filter for quality. The older the problem, the older the solution. Read books that’ve stood the test of time. When in doubt, have a bias towards old, weird books. 

5. Favor Biographies over Self-Help

Walk into a book store, and you’ll see tons of self-help books on the recommended shelves. Unless you counter with some resistance, you’re likely reading too many self-help books.

Biographies are written about outliers. The best biographies are the ones the subject doesn’t approve of. Life is messy and complicated. A good biographer tells a fair and balanced story — they balance the good with the bad. Through biographies, you explore the cost of ambition and the price of success. 

You don’t just learn about a person. You learn about their time and place. Let biographies age before you read them. In general, the older biographies are better. 

Learn To Love it

At the end of the day, the most important part of reading is enjoying it. If you don’t enjoy reading, words won’t engage you, and if words don’t engage you, you’ll stop reading. Don’t let that happen. Do everything you can to enjoy reading. 

Get on your way and learn to love it. 

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1: From Bret Victor, a reading list of meaty material from the past year. His Reading Tip #1 in the sidebar is how I’d like my ideal self to read:

It’s tempting to judge what you read:

“I agree with these statements, and I disagree with those.”

However, a great thinker who has spent decades on an unusual line of thought cannot induce their context into your head in a few pages. It’s almost certainly the case that you don’t fully understand their statements.

Instead, you can say:

“I have now learned that there exists a worldview in which all of these statements are consistent.”

And if it feels worthwhile, you can make a genuine effort to understand that entire worldview. You don’t have to adopt it. Just make it available to yourself, so you can make connections to it when it’s needed.

2. Since I have limited experience reading fiction, these recommendations are biased towards non-fiction books. With that said, I’m trying to read more fiction. If you have suggestions, please let me know.



I’d to hear your feedback. Send me your thoughts, criticisms, and ideas in a direct message on Twitter. When you do, please don’t nitpick. Constructive feedback will lead to a more productive dialogue that’ll be better for both of us.