Five years ago I was challenged to read 30 books in a year. I accepted that challenge and wrote about what I learned at the end of the year. I’ve since made it a point to read at least 30 books a year and my life has been greatly enriched by doing so.

I read a lot of great books in 2018. In no particular order, here are my 10 favorites.

10) When: The Scientific Secrets of Perfect Timing by Dan Pink

This is the fourth book I’ve read from Dan Pink, which goes to show how highly I think of his work. There are a lot of “how-to” books out there, but as the title suggests, this is a “when-to” book. Pink explores the science of timing and answers many questions including:

• How can we use the hidden patterns of the day to build the ideal schedule?
• Why do certain breaks dramatically improve student test scores?
• Why should we avoid going to the hospital in the afternoon?
• Why is singing in time with other people as good for you as exercise?
• What is the ideal time to quit a job, switch careers, or get married?
  

Regarding the last question, Pink found that people who change jobs frequently early in career end up making more money than those who don’t. Why? As it turns out, the likelihood that you’re going to start your career in a job that you’re good at AND enjoy is relatively low. Changing jobs early in career gives you more chances to find the right match. He also shared that one of the main reasons starting your career during a recession can be so damaging is that it limits your ability to change jobs and you end up staying somewhere that’s not a good fit.

9. Trust Me, I’m Lying: Confessions of a Media Manipulator by Ryan Holiday

Ryan Holiday is one of my favorite writers. While most of his books focus on stoicism, his first book details how easy it is to manipulate the media. I knew this book would expose the underbelly of media organizations but I was still shocked to learn how it all works today.

8. Thinking in Bets by Annie Duke

We read Thinking in Bets for our DoorDash book club earlier this year and I initially wasn’t interested in it. It looked like a book about poker, a subject I don’t particularly care about. But I quickly learned it’s really a book about getting comfortable with uncertainty and making better decisions.

My biggest insight was realizing how often I base the quality of a decision on whether there’s a positive or negative outcome. Good outcome and I deserve a pat on the back. Bad outcome and I’m kicking myself. But in reality, decisions should be evaluated on information that’s available at the time, not on how things play out. When making decisions we often have limited information and an even more limited understanding of the risks. The more we can quantify those factors, the more we’ll end up making good choices.

Whether you read the book or not, think back to the worst decision you’ve made over the last year. If you’re like me, you immediately thought of a decision that led to a bad outcome, even if the decision itself may have been completely sound. Focusing on decision making process over outcome is the right way to do it and will yield to more good decisions in the long haul.

7. Dream Teams: Working Together Without Falling Apart by Shane Snow

Shane Snow is an amazing storyteller and weaves in clever anecdotes and thorough research to convey how we can build strong and impactful teams.

6. The Power of Moments by Chip and Dan Heath

Fantastic book on how to use defining moments to transform your life and business.

5. Tiger Woods by Jeff Benedict

There’s an argument that Tiger Woods is the greatest golfer of all time. There’s no argument that he revolutionized the sport and dramatically increased its popularity since first winning the Masters in 1997. Tiger was lethal in his prime, winning over 30% of the tournaments he entered during a 12-year stretch. He dominated the competition. (Here are his 40 most impressive feats.)

Much of the credit for Tiger’s greatness can be attributed to his father, Earl, who pushed him relentlessly. I knew his dad was intense, but this book opened my eyes to the extreme ways Earl pushed his son. It also opened my eyes as to how hard Woods pushed himself to be the best, and how, in his quest for greatness, he ultimately destroyed his family and frayed many close relationships. The book is outstanding and the Bill Simmons Podcast interview with Chuck Klosterman covers the most riveting parts.

For me, Woods’ rise to greatness stands as a cautionary tale. He accomplished so much, but at what cost? Climbing to the top of your field, whether it’s sports, business, or anything else, requires an almost myopic focus. Before we begin our climb, it’s worth asking ourselves, today, what is the ultimate goal we’re trying to accomplish? Or as Harvard professor Clayton Christensen asks, how will you measure your life?

4. The Five Dysfunctions of a Team by Patrick Lencioni

A leadership fable that teaches how teams can overcome obstacles to achieve success. I really enjoyed Lencioni’s writing style and was engaged throughout the book.

3. The Courage to be Disliked by Ichiro Kishimi, Fumitake Koga

Earlier this year my friend tweeted, “Marc Andreessen thinks everyone should read this book right now: Adlerian psychology meets Stoic philosophy in Socratic dialogue. Compelling from front to back. Highly recommend.” So I bought it, and, and I’m glad I did. Written as dialog between a philosopher and a young man, The Courage to be Disliked was only recently published in English, but apparently sold over 3.5 million copies across Asia.

I drew a lot of insights, but my favorite lesson is connected to the book’s title. “Real freedom is the courage to be disliked. You’ll never be truly free unless you are willing to be disliked by others. The courage to be happy and the courage to be disliked go hand in hand.”

Amazon shows only 5-star and 1-star reviews, and I can see why. Some principles are simple and obvious, while others (past trauma has no impact on your ability to be happy) are much harder to swallow.  I don’t agree with everything taught, but it gave me a lot to think about. To me, that’s the sign of a great book.

I listened to the Audible version but it’s likely just as good in print. For a more thorough overview, check out this article.

2. Educated: A Memoir by Tara Westover

I loved this book. Might be the best I’ve read all year. There’s no business angle to Educated but I thought I’d share given that I literally couldn’t put it down.

1. Powerful: Building a Culture of Freedom and Responsibility by Patty McCord

From DVDs to streaming to original content, Netflix has reinvented itself several times. These reinventions were made possible by a unique culture that differs wildly from its Silicon Valley contemporaries. Netflix’s former HR leader shares the secrets of what makes that culture so effective.