In a world where a new book is published every hour, it's important to mark the ones that stand the test of time. Below are my recommendations.
The Mind is Flat - Nick Chater
To me, psychology books are interesting but not particularly applicable to everyday life; they focus on the mechanisms which make the brain work but hardly touch on the experience of having one. Conversely, books that focus on only what it means to better use your brain on a daily basis (say, those in the self-help section) tend to present logical solutions to specific problems but shy away from the mechanisms that make those solutions likely to work. The Mind Is Flat is a book that presents like the first, but has implications that feel like the best examples of the second. Chater demonstrates that the idea of “subconscious thought” doesn't exist and that the mental cycles needed to do math, remember a photo, or say “I love you” are entirely rooted in the present. His simplified model of the mind, if correct, explains how habits work, why dealing with trauma takes a huge amount of effort, and why your environment is the most important factor in determining your lifestyle, mental health, and ability to make changes. What I found most exciting is the possibility that the way people think, while very complex, is possible thanks to a few somewhat-simple processes. Buy it on Amazon.
Thinking In Bets - Annie Duke
Everything that we do in business is about making the right bets, and enough of them, to create the outcomes we need to continue doing business. Sometimes the best way to practice navigating something as complex as business is to play games - for example, like poker. Annie Duke has accumulated more than $4 million in poker winnings in her career. In her book, Annie sheds some light on the methods she and her poker-playing friends used to understand the context of each hand, each opponent, and each potential card combination. One of the best lessons from this book is that events in life and work are unpredictable no matter how much preparation you do. It's normal, in fact expected, to be unable to make accurate predictions, and so the best thing that you can do is familiarize yourself with the variables at play and the scenarios that lead to the outcomes you prefer. Although Thinking In Bets is a book meant to draw parallels between poker and business, I believe the betting mindset has applications in most of life. Buy it on Amazon.
The Infinite Game - Simon Sinek
It's not very often that a pop-business book can make me gesture wildly in my airplane seat. This is that book. Simon Sinek writes books about mindset, specifically, the mindset to have when you're trying to manage a team and grow a company. In The Infinite Game, Sinek explains the perils of win-loss thinking in your business strategy. He goes on to describe how doing business isn’t something you win, but simply something you do you keep doing more business. What I really love about this book is what happens after I closed it: I became very aware of my bias towards win-loss thinking, and it ultimately helped me orient my decision-making towards creating effective, sustainable systems of business (perhaps despite the conventional wisdom of today’s business leaders and venture capitalists). I highly recommend this read to anyone who's thinking of starting their own business or contributing to a well-established one. (Additionally, this book is a nice add-on to the mindsets presented in Thinking In Bets.) Buy it on Amazon.
So Good They Can't Ignore You - Cal Newport
I have bought this book for a number of people because when I first read it in 2015 it completely changed my attitude on work. The lesson of this book is pretty short: despite conventional wisdom of turning passion projects into a full-time job, career-building is a tough, time consuming process and you really don't have control over when the opportunities come around. People often attempt to force control over their career in order to gain a feeling of security and self-esteem, but it usually results in a stalled career trajectory because its nearly impossible to fake genuine experience. Newport's describes the process of building “career capital” through a combination of high-quality output and effective optics as the proven method for climbing the proverbial ladder. Ultimately, I learned that being rewarded for my work wasn’t actually about me, so the only thing I can change is the quality and accessibility of the work. Read this book right now. Buy it on Amazon.
The Hard Thing About Hard Things - Ben Horowitz
Business exist because people build and manage them, and rarely is there a business that does not involve other people in critical roles. Horowitz makes it painfully clear that business is a bumpy ride and it takes strong leadership and incredibly difficult choices to see it through. Sometimes, people grow with the business, and sometimes they don't. While not every business journey will feel quite the same as the one that this book documents, it's inevitable that you will face challenges like office politics, hits to morale, missed targets, strained friendships, unexpected innovations from competitors, and managing talented jerks. One special moment in this book is when Ben "pays it forward" to author Andy Grove for sharing his advice on training team members, which ultimately led me to pick up a copy of High Output Management (also in this list). Buy it on Amazon.
Wealth, Poverty, and Politics - Thomas Sowell
I picked up this book shortly after reading (slogging through) Piketty's Capital in the 21st Century. Sowell's 500+ page study doesn't try to outright disprove the arguments made in Capital about economic inequality, but it adds a lot of color to who those groups of people are and how they may have ended up as rich, poor, or somewhere in between. What I really like about this book is that it walks through as many angles as possible, starting with geographic factors associated with wealth, then cultural factors, social factors, and finally political factors. For example, Sowell argues that nations and peoples who intentionally isolate themselves (in many ways) are guaranteed to become more poor over time. Sowell is known to be politically conservative so I did my best to skip over most of his conjecture regarding why people do what they do and how it applies to the present, but the research portions of each chapter are interesting. Overall, this one is absolutely worth a read. Buy it on Amazon.
A Random Walk Down Wall Street - Burton G. Malkiel
If I didn't read this book, I probably would have had the same experience with stock market investing as I have had with casinos, that is, quickly losing all of the money I brought in to wager. Most advice about casual stock market trading is garbage because, as Malkiel outlines, the market itself is driven by too many factors to be predticatble. In fact, the only thing you can do to guarantee the growth of your investments is to reduce risk by investing in as close to the entire market as possible (and even then you are at the mercy of the health of the economy). There are lots of books to read which recount moments of financial ruin thanks to bias and hubris, but Random Walk is one of the best choices if you want to demystify stock market investing in general. Pair this book up with Thinking In Bets and The Infinite Game for a crash course in managing complex systems. Buy it on Amazon
High Output Management - Andrew S. Grove
There is a reason that Andy Grove is known as one of greatest influences on technology company management - even though the first edition of High Output Management was published in the 80's, this book has aged extremely well. The chapters use lots of metaphors to describe key concepts like leverage, quality, process, and performance. Grove is methodological but empathetic; this book could have been entirely about the mechanics of production but he instead focuses on how to treat employees and build a culture of high-performance. As Ben Horowitz mentions in his book The Hard Thing About Hard Things, correcting unwanted behavior and letting people go is hard to do, but ultimately up to the leadership to address. High Output Management introduces a new way of thinking for its time; you'll need to pick up newer reads to supplement and expand Grove's points. Regardless, I feel that it remains one of the best foundational management books to prepare you for any business journey. Buy it on Amazon