A Guide to Choosing Which Books to Read

Tim Urban over at Wait But Why wrote a great perspective post by putting life through the filter of time and then breaking it down by activity—how many winters, Super Bowls, books, etc. are there to be experienced and consumed in a 90-year lifespan? If I’m 32 (and I am), that leaves 58 (hopefully good) years left in my life, and if I read, on average, twenty books a year, that gives me ~1,160 books to pour through in the next several decades. That number may seem like a lot, but when (according to Uncle Google), there are 130 million books out there that have ever been published, and another 600,000-1,000,000 books continuing to be published every year, 1,160 books means I’ll just be able to get through ~0.000003% of all books by the time I hit 90. A real big, fat, dent.

Not.

So, knowing this, how do we decide which books to read? Where do we even begin when the paradox of choice presents itself in such monstrously overwhelming and paralyzing way? How do we find those more obscure books, perhaps, that few have heard of?

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WHY READ

For me, it’s important to understand why I read. Reading for entertainment results in very different choices than reading for knowledge and growth. There’s no right or wrong, better or worse. While I tend towards books that challenge an existing perspective or teach me something new, I still enjoy sprinkling in a book for “fun” every so often (i.e — talk to me about the Red Rising series). I try to keep a 4:1 ratio of “knowledge” to “entertainment” when it comes to what I read, as in, for every four books I consume for knowledge or growth, I’ll read one for fun. That said, more often than not, the books I read for knowledge or growth end up checking the “fun” box, too (though not always). It can be tough at times to distinguish between the two, so for the sake of clarity, I run through four questions to help me think through which category a book might fall into:

  • Is the book classified as a non-fiction?

  • Is the book considered literary fiction or a “classic”?

  • Is the author known for his or her prose/writing style?

  • Is there a central, big idea or hypothesis the author is attempting to prove?

  • Has the book laid claim to one of the world’s most prestigious literary awards?

If I can answer “yes” to any one of the five questions above, then the book falls into the knowledge/growth category. These questions are by no means fail-proof, and inevitably, upon completion of a book, I may find it flip from one to the other, which is fine. But this still serves as a nice framework to help me think through the type of books I want to dedicate most of my time towards.

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DISCOVER NEW BOOKS

There are three main ways in which I discover new books to potentially add to my reading queue on Goodreads (my all-time favorite “social networking” site):

  1. Recommendations from friends and/or through conversations with people. If a friend or family member gifts or recommends a book to me, I’ll (at the very least) look into it before deciding whether or not to proceed. A good recommendation usually comes from someone who knows me well, knows what kind of books/authors I’ve read and enjoyed, and has some knowledge of the kinds of topics that pique my interest. For this reason, the best recommendations typically come from my partner. Sometimes, a book will find its way into a conversation I’m in or one I overhear, perhaps someone references an idea from the book, and I’m intrigued. I’ll usually jot it down and look into it later.

  2. Reading lists or recommendations from people I admire and aspire to be like. This is a big one. Not all reading lists and recommendations are created equal. I don’t check “The New York Times Best Sellers’” lists or any “best sellers” lists for that matter, and give little credence to books claiming that on their covers. I won’t click on some rando’s “My Top 5 Books of 2018” unless I’ve done sufficient research on that person and have decided I care about what they have to say (which means you probably shouldn’t click on mine). That said, I will click on Sam Harris’s book recommendations, or Shane Parrish’s, Maria Popova’s, Naval Ravikant’s and Derek Sivers’s. I’m hungry for whatever these folks put out. They are the small handful of people whose work I consume on a regular basis, whose opinions and judgements I care to hear. Their minds contain multitudes, their work and writings reveal interdisciplinary, polymathic knowledge and their reading lists are a reflection of such. They are inspirational human beings. If I could choose five people with whom to surround myself, they would be it, and perhaps by proxy of being around them (or by osmosis), I’d become a polymath myself. You might not care about Sam Harris, or perhaps you’ve never heard of any of the people I’ve listed above. This point is still relevant—seek out the people you look up to, whether it’s in your own life or public figures, ask them what they’re reading, go to their websites/blogs to see if they’ve shared book lists and recommendations. Often times, Googling their name along with “book recommendations” will yield a shocking amount of articles. Public figures like Bill Gates, Sophia Amoruso, Mark Zuckerberg, Jeff Bezos, Warren Buffet, etc. are all avid readers who openly share what they’re reading. You’ll have no shortage of books to check out and add to your queue once you’ve gone through a couple of their lists.

  3. Goodreads. This site has been invaluable to me; (a cautionary note: it was bought out by Amazon a couple of years ago, so if you’re concerned with privacy and Amazon having too much data on you, you may want to stay away). That said, I am exposed to a vast array of books because of the diversity in my network. You can choose to keep your network to only people you know or widen it to include strangers, authors, etc. (similar to Instagram). There are pros and cons to each. But if you want exposure to random, obscure books from various genres, then it helps to branch out and befriend people who are unlike you (you can always “unfriend” them later if you decide their book choices are too wacky). I liken combing Goodreads to thrift shopping (especially if you don’t know what you’re looking for), there’s a lot of junk and stuff that won’t resonate with you, but with a little patience and a practiced eye, you’ll come across a vintage piece that just might change your life. 

These methods are what work for me. You don’t have to limit yourself to these three. Sometimes, I’ll walk the aisles of my local bookstore in the Mission—Dog Eared Books, to envelope myself in the scent of old books, touch the time-traveled covers and feel the weight of knowledge in my hands. I’ll read the little notecards marked as “Staff Favorites” for that week or month and have picked up a couple of books this way. It’s similar to surfing through books on Goodreads, but with more sensory input. Joining a book club is another great way to discover new books. 

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FILTER THROUGH WHICH BOOKS TO ACTUALLY ADD TO YOUR READING QUEUE

Do your due diligence. Not every book recommended or gifted to you has to be read. Life is too short to be spent reading books of little relevance and interest to you. Don’t blindly read a book because it landed in your lap. Know what you’re reading, why and how best to read it. The upfront cost in time and effort to research what a book is about and what the author stands for will pay for itself later. With little to no research, you may end up with a bookshelf (virtual or physical) full of books you started but never finished. And while it might look nice to have such a varied collection of books in your house, it’s no fun to put yourself at risk of imposter syndrome.

So, filter, filter and filter some more. Don’t buy a book just because your best friend said it’s her favorite book. Buy the book because you’re genuinely interested in the story, idea or philosophy, or because you’re a fan of the author. Don’t read a book because a family member gifted it to you for the holidays, read it because the book speaks to you and is relevant to where you are in life. And along the same vein, don’t not read a book because you think the person who recommended or gifted it to you is a weirdo, or because their perspective on something is plain “wrong,” read it because you’re curious about the other perspective. Read it to gain a better understanding of his/her mindset and lifestyle choices, even if you end up using it against them in friendly debate later on! Know your answer to the question, “Why are you reading this book?”

Below are the steps I take upon first hearing about a book and actually adding it to my reading queue:

  1. Take a few seconds to jot down the title of the book that piques my interest (i.e - I Contain Multitudes, a friend mentioned it when we were talking about microbiome/fecal transplants.)

  2. Spend 2-3 minutes searching the book on Amazon, Google and/or Wikipedia to skim the summary, author bio and scan through reviews. Usually, I’ll read 2-3 reviews from each star variation (5-stars, 4-stars, 3-stars, 2-stars, 1-star) for a total of 10-15 reviews. If at this point, I lose interest, then I move on to the next book on my list. If I’m still intrigued, then I’ll move on to the next step.

  3. Spend another 2-3 minutes searching the book on Goodreads. I keep this as a separate step from the above for two reasons: first, I find the reviews on Goodreads to be more geared towards the content of the book itself, whereas Amazon’s reviews are sometimes inclusive of book formatting, editions, shipping, etc., and second, I like to see who in my network has already read this book and what they thought of it. I tend towards reading more reviews on Goodreads than on Amazon, and acquaint myself with the reasons for why a book was phenomenal to some and dreadful to others. You start to recognize common patterns and reasons for why people rank a book 4-or-5 stars vs. 1-or-2 star(s). At this point, I’ll decide whether or not I can tolerate the negatives for the potential positives. For example, people who gave I Contain Multitudes 1-or-2 stars seem to have a problem with the lack of evidence and sound science in the author’s narrative. They found it boring and had a problem with the way the book is organized. People who gave it 4-or-5 stars (more stars tend to also equate to more detailed reviews) seem to appreciate the wealth of information the author provides on the topic of bacteria. Some of them acknowledged the lack of specific evidence and deep dive into current research, but from these reviews, I can surmise the book probably focuses on breadth rather than depth, as is typical of most popular science books. Because I know little-to-nothing about bacteria and how they exist in our world, this book, for me, seems like a good enough introduction and is worth my exploring further. Often, I’ll lose interest in a book at this step, perhaps the negative reviews speak louder to me than the positive ones, and that’s that. But this is also the step where I usually have enough information to decide whether a book is worthy of being added to my “Want to Read” queue on Goodreads. In the case of I Contain Multitudes, it’s been added to my queue and I’ve now completed my due diligence. In rare cases, I may need more information about a book, in which case, I’ll resort to the next (and final) step.

  4. Take an extra 5-10 minutes researching and skimming through articles about the book and/or author. If I’m still on the fence about a book, then I’ll deep dive further into the book and author. I’ll read through articles, op ed columns, reviews, etc. perhaps on The New York Times or The Atlantic. If the author has a led a TED talk about the book’s research, I’ll watch that. I’ve never gotten to this step and not known whether or not to proceed with the book, but if this happens to you, you can either create a separate list or shelf on Goodreads and title it “Undecided.”

It may take closer to five minutes when you first start this process, but it’ll get faster and faster each time. I like to set aside 15-20 minutes once every couple of weeks to go through all of the books I’ve stumbled upon, and can usually filter through a dozen books in under twenty minutes. Whereas in the past, I’d finish 50% of the books I start, with this process, I now finish 80-90% of all books I buy and start.

Be stringent about the books you add to your “Want to Read” list. Say no to more books than you say yes to. Ask yourself, “Will I gain as much or more from this book than the energy and time I exert?” It’s a hard question to answer prior to starting a book, but it’s a good one to keep in the back of your mind once you do. If a book ends up draining you (and that’s different than challenging you), then it’s a good sign to set it aside and walk away. There’s no shame in not finishing a book, as Naval Ravikant will tell you, give yourself permission to quit!

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DECIDE WHICH BOOK(S) TO CONSUME NEXT

So you have a reading queue with dozens, perhaps hundreds of books. Now what? Paradox of choice is still an issue even after you’ve narrowed your pool. You might be a one-book-at-a-time reader or maybe you’re more like Naval Ravikant, cofounder and CEO of AngelList, who advocates reading 10-50 books at any given time. There are pros and cons to each, so it’s up to you to experiment and see what resonates. 

Most of the time, I pick my next books by feel (i.e — I’m feeling a fiction, or memoir or sci-fi, or I’m feeling a non-fiction on the subject of relationships or communication or cognitive psychology, etc.), but even then, there are a few guiding questions I’ll run through in my head to help solidify what to read next:

  • What genres were my last 2-3 books? If I just finished a fiction, I’ll usually switch over to non-fiction. If my last several reads were non-fiction, I’ll usually go through my queue for a new novel. A little diversity is always nice.

  • How, when and where have I heard about this book? Often, it’ll be clear to me what my next book is simply because the universe seems to be pointing me towards it. Maybe someone on a podcast will have randomly mentioned it, or it comes up in conversation at dinner, or someone posts a quote from the book on their Insta-story. Once a book has manifested itself to me three times, I’ll bump it up in my reading queue.

  • Is this book a full departure from I’ve been reading/learning/thinking about lately or will it round out my knowledge on a topic? I try to segment my readings and learnings into themes, so it allows me to dive deeper into a topic, develop an informed, well-rounded opinion and possibly even formulate a fundamental operating principle or philosophy. Reading one singular book on a topic can only get you so far (unless it’s fiction). For example, for the past several months, I’ve been really into spirituality, psychedelics, meditation and Buddhism and so have read more heavily into books focusing on these interconnected topics.

  • How urgent and important is it that I read this book right now/next? Sometimes, I’ll pick up a book because I need to learn something quickly. Books about business, marketing, sales, startups, etc. provide new ways to think through existing problems or help me get ahead of a problem before it transpires. I picked up Michael Pollan’s How to Change Your Mind and James Fadiman’s The Pyschedelic Explorer’s Guide just before my first-ever full hallucinogenic experience.

  • What will be occurring in my life in the next couple or several weeks? I like books to complement and supplement my schedule, lifestyle and activities. If my partner and I decide to go for a big health reset (whether by going keto for a few months or a full-blown elimination diet), then I’ll read books related to health as a way to unify my intellectual learnings and experiential learnings. If I’m going on vacation, I’ll pick up a fiction or sci-fi book. If I need to hone my writing skills, I’ll gravitate towards books about writing and literature. 


It’s possible I’m a freak for having such a meticulous process for simply deciding what to read. It may seem excessive, inefficient or time-consuming to some, but the process is so entrenched in my mental processes and weekly habits, it takes up no more than 15-20 minutes every few weeks. It’s a slightly heavier up-front investment in time but ends up saving time and money later on as I’m significantly more likely to finish a book I purchase/start.

If you have a process for discovering new books or deciding what to read next, please share! I’m always curious for new ideas, perspectives and inspiration.