My Secret Education: 32 powerful books that have transformed the way I think and how I approach my life

I love learning.

Yet, I wouldn’t always have described myself that way. I used to do it for grades. Now I do it for fun.

Growing up, I wasn’t that big of a reader. I read the books assigned at school and never much more (though I did go on an impressive Goosebumps kick). A couple assigned books stood out. Tale of Two Cities was pretty fantastic. To Kill a Mockingbird was quite memorable. Though that might have been because of the weird voice my English teach made when he said “Boo Radley.”

When I was in college, I stumbled upon Freakonomics. It blew me away. It exposed me to a feeling that I never experienced before. It was a mix of bewilderment, amazement and excitement. It’s that moment when you are exposed to a new idea that is convincing, yet controversial to the worldview you held five seconds earlier. I’ve always been susceptible to new ideas, but this book unleashed a curiosity that hasn’t stopped to this day.

Once I plowed through the usual suspects like Freakonomics (see: Malcolm Gladwell, et. al.), I started exploring more. I read about things I knew nothing about (my roommate’s book on Advertising) and constantly sought out others for suggestions. When books didn’t satiate my curiosity, I started reading longform. Then came podcasts and even online courses.

The benefits of this drive have been immeasurable. What follows are a selection of the many books I have read in my life — 32 books that have transformed the way I think and the way I approach my life. But more, it is a list of books that have given me a secret edge. Ways to optimize my performance, ways to learn faster than others.

Alas, my secret education:

1. Freakonomics by Stephen Dubner and Steven Levitt 
This one is obvious if you didn’t skip to the list, but it made me think in a different way and helped me develop a healthy contrarian or skeptical outlook to analyze business problems and identify opportunities that most people don’t see. A lot of brilliant ideas start from questioning conventional wisdom — just like Levitt and Dubner did.

2. Predictably Irrational by Dan Ariely 
This book lands on the list because a lot of the experiments were done in my favorite grad school bar (Beacon Hill Pub). On top of that, it helped me understand that humans all are in fact, irrational — we say one thing and do another. The rational being is a myth. One interesting experiment he did was offer people a Budweiser and a Budweiser with balsamic vinegar. Most people preferred the beer with the vinegar. That is, until they were told what was in it beforehand. Sip on that…

3. Tuesday’s With Morrie by Mitch Albom 
I read this book when going through a health challenge and it helped sharpen my understanding that the personal relationships, with family and friends, are what gives me strength in life and my career — not the other way around. Mitch Albom gets to know an otherwise ordinary man, Morrie — who in fact is one of the most incredible people you will ever “meet.” Definitely read this book.

4. The Last Lecture by Randy Pausch 
Continuing in the same vein as Tuesday’s, this book is literally the last lecture given by Professor Pausch. His topic is achieving your dreams. If this book (or video if you wish) doesn’t move you to tears, I don’t know what will.

5. Influence by Robert Cialdini 
 I was assigned a chapter of this book to read in grad school for the “Organizational Processes” class and was blown away. I immediately got the entire book and ended up skipping a class or two to finish it. It dives deep into the elements that enable people to be persuasive and influence others. For example, people are more likely to follow a man in a suit across the street during a do not walk sign than someone dressed less dapper. The way we present ourselves to the world and communicate matters.

6. A Random Walk Down Wall Street by Burton Malkiel 
One of the books I read after Freakonomics — I realized I never wanted to have to rely on other people for understanding investing, the financial markets and financial planning. This book taught me the reasons why buy and hold strategies and low cost index funds are vital to creating long-term wealth even though it is easy to get caught up in believing that’s not the right approach.

7. How Will You Measure Your Life? by Clayton Christensen 
 Many know Clayton as the disruptive innovation guy, but he is much more than that. Christensen is a reflective and powerful business leader and teacher. He is passionate about how the business world can create incredible opportunities to do good. His quote, “…if you want to help other people, be a manager. If done well, management is among the most noble of professions…” transformed my cynicism of the corporate world into hope and made me realize I can make a difference by seeking to create incredible experience for people within the corporate world.

8. Why do all Black Kids sit together in the Cafeteria? by Beverly Tatum 
This book opened my eyes to understanding there is a lot in the space that “I don’t know what I don’t know.” Tatum walks through identity development of African Americans, especially her own and made me realize that I, as a white male, never actually went through anything like that. Life was pretty easy for me. It helped me to be more empathetic of people, helped me understand what privilege meant and why diversity and inclusion matter so much for creating a better world.

9. Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain
 I thought I had a good understanding of introversion and extroversion until I read this book. This book also made me realize I was a lot more introverted than I realized. This is where I first heard of the term “ambivert” and realized I am energized by a mix of alone time and activity with others. I was fascinated by the history of how extroversion became such an ideal in modern society and the mistakes that can lead us to make.

10. Drive by Daniel Pink 
This book brought to life many of my suspicions — that the corporate world does not use all the best ways to motivate and inspire people. Pink shows that there is huge gap between what we know about motivation and leadership in the workplace and what people and companies actually do. It’s my goal to help close it.

11. The Art of Learning by Joshua Waitzkin 
This book is a masterpiece. Waitzkin walks through how he became a chess champion at age 8 and brought Gary Kasparov to a draw at 11 years old. After quitting chess, he applied the same approach to Taiwanese push hands and became world champion. His concept of “numbers to leave numbers” brings to life the journey of mastery, helping me understand that you need to understand the details before you can take a step back and be a master of the big picture.

12. Work Rules! by Laszlo Bock
 I would consider Laszlo a role model. Not because we both worked at GE and McKinsey, but because of his passion for people. I share a mission with him — to make the working world an incredible place. He offers many free or low cost ways to improve people’s experiences and talks about how conventional wisdom and a lack of caring about people are what holds us back. There is a lot to learn from him and his experience at google.

13. Nothing Special by Joko Beck 
This was the first book I read about Zen Buddhism and mindfulness. The story is a conversation between Beck and her students and will resonate with anyone who is curious about mindfulness, meditation and spirituality.

14. Mastery by Robert Greene
 Another masterpiece. Greene brings to life the journey of historical and modern day masters and provides incredible detail into their journey. We generally accept Michaelangelo and Einstein as brilliant, but don’t hear about the many years they were not considered brilliant. He even shows cases where “masters” were correct, but did not win over enough support to achieve their dreams in their lifetime. A couple interesting examples are the fact that Stephen King wrote every single day for NINE YEARS before selling a single book or Leonardo da Vinci didn’t have his big break until he was 46 (the last supper). My number one takeaway from this book: Find a purpose, find teachers and mentors and then be more patient than you want to be.

15. The Good Jobs Strategy by Zeynep Ton
 Written by my favorite professor from MIT, she presents a convincing and proven account of how treating employees well and paying them above average wages helps companies outperform their competition. She provides traditional examples like Trader Joe’s, Costco and Southwest but also presents unexpected examples like the convenience store QuickTrip to inspire others to believe that this model can work anywhere.

16. The Righteous Mind: Why Good People are Divided by Politics and Religion by Jonathan Haidt 
For anyone that gets frustrated by other’s tunnel vision on politics and wants to understand why they think that way, this book is for you. This book gave me incredible understanding into how people develop their political identities and helped me gain an appreciation for people who are religious. Warning: this book will raise your understanding of other’s views and become more apathetic towards political arguments.

17. Counselor: Life At the Edge of History by Ted Sorensen 
As a consultant and someone that has worked with senior leaders, I found Ted Sorensen’s account of being JFK’s closest adviser compelling. He shares how he was able to bring JFK’s voice to life and how he was able to have an influence on him to make him a better President and leader. The incredible focus and detail the two spent on the words used for letters to Gorbachev during the Cuban mission crisis show the importance of language and influence while provide a fascinating look into one of the most stressful moments in American history.

18. How to Win Friends and Influence People by Dale Carnegie 
This is a classic for anyone interested in building strong relationships, both in your personal life and professional life. His approaches are timeless and dispel myths around “nice guys finish last” — he shows that you can influence people to change their mind by listening rather than speaking and putting yourself in the other person’s shoes. No-brainers of course, but the way he writes is powerful and easy to understand.

19. Moonwalking with Einstein: The Art and Science of Remembering Everything by Joshua Foer 
This book deepened my belief that we are capable of more than we believe. Given our reliance on technology, a good memory is not valuable in today’s world. Yet, that wasn’t always true. Foer makes it his mission to become a memory champion. He starts off with an average memory and builds his skill to become USA Memory Champion in “speed cards,” memorizing a deck of 52 cards in 1 minute, 40 seconds. I’ve use some of his memory tricks to remember people’s names and they are quite effective.

20. The Halo Effect by Phil Rosenzweig 
This book offers a contrarian view on most popular business literature. He shows that only up to 30% of business performance can be explained by leadership or strategy. The rest is determined by free market dynamics, economic changes and competition or unknown forces. This book makes you think twice about crowning someone a “great leader” and thinking twice before declaring a business executive an incredible leader. Are they or did they just luck out with the right company at the right time?

21. The Happiness Hypothesis: Finding Modern Truth in Ancient Wisdom by Jonathan Haidt 
Another great book by Haidt. This book is about the pursuit of happiness and the things that make us happy. There are many things we think make us either happy or unhappy, but do not. We would be happier if we spent more time and money on experiences than things, yet Americans are taking less vacation than ever. I’m writing this on vacation as I overlook Monterey Bay, so I may just be drinking the kool-aid…

22. Steve Jobs by Walter Isaacson 
Everyone knows the basic Steve Jobs story but this book breaks down the detailed conversations and journey to becoming one of the most accomplished business leaders in the modern day. Jobs seemed to succeed and fail based on his extreme views, which range from only eating fruit to his obsession with greatness at Apple. One think I took from this book was his love for walks and using them for meetings with people. I try to incorporate walks into my day as much as possible.

23. 1776 by David McCullough
 This book was a lesson in I don’t know what I don’t know. The majority of the fighting of the revolutionary war during 1776 took place in New York City, not Boston — which I found shocking. I was also dumbfounded by the fact that it was common for armies of that time to take the winter off. The Americans scored a key victory that year because they planned a surprise attack in the snow, in New Jersey of all places.

24. The Autobiography of Benjamin Franklin by Benjamin Franklin
 This book is fascinating as it is Franklin’s self-told journey through his life. Franklin stands out for his ability to take action — if he saw something that needed creating — he did it. From a firehouse to a library to an improved printing press, he was creating, building relationships and pursuing excellence. This is also notable for his breakdown of virtue and interesting attempts to be more “virtuous” by logging his daily activities.

25. Meditations by Marcus Aurelius 
This book is incredible because it was written over 1800 years ago, but its tone and message are still relevant. Aurelius was reflective and self-aware and had the unique position of being Roman emperor. He drops so many knowledge bombs like this that still ring true today: “ Put an end once for all to this discussion of what a good man should be, and be one.”

26. Antifragile by Nassim Taleb 
This book blew my mind. Though at times a bit egocentric in his style, Taleb has read hundreds of historical writings and has synthesized the wisdom for us — much of it that runs counter to conventional wisdom. He argues that systems thrive on an ability to absorb shocks and strengthen because of it (being antifragile). He shows how things such as vaccines, creative destruction and even fasting are ways that systems become stronger from negative shocks. He If you enjoy philosophical wisdom and questioning conventional wisdom, this book is for you.

27. The Signal and the Noise by Nate Silver 
Silver, of 538 fame, talks about how statistics are often used poorly and how to use them in decision making. The main idea I took away from this book was that the outcome does not determine the quality of the process. It is often a mistake to say that you took the right approach if you achieved the goal you want. He offers a probabilistic view of the world. If you are going to be correct 70% of the time and you get a negative result, it doesn’t mean you took the wrong approach. I see people make this error all the time in the business world.

28. There are No Children Here: The Story of Two Boys Growing up in the Other America by Alex Kotlowitz 
This book tells the story of two incredible boys who grew up in the south side of Chicago. It heightened my appreciation for the genetic lottery I won and the wonderful childhood I experienced. The challenges these two boys faced just to stay alive, yet alone thrive, are eye opening and highlighted challenges we still face in our country.

29. The Omnivore’s Dilemmaby Michael Pollan 
I have dealt with some health issues and doctors always told me, “you need to improve your diet.” It was not until I read this book that everything clicked and I realized how much food quality matters. As a systems thinker, his breakdown of the entire food production process was powerful, showing how different factory raised meat can be from naturally raised meat. This book triggered a dramatic change in my approach to what I eat and also helped me increase my energy and mental performance. Thanks Mike.

30. Everything Bad is Good for You by Steven Johnson 
This book destroys the notion that “things are getting worse.” For example, he talks about how people bemoan the low quality of today’s reality TV, but shows that the worst TV shows of 50 years ago were a lot worse than those. You can’t compare great shows like I Love Lucy to today’s worst shows — you have to compare it to the best. Shows like Soprano’s and Breaking Bad are in fact a lot more complex and intellectually stimulating than any show from the past. He also talks about intelligence and a phenomenon called the “Flynn effect,” the fact that people have been getting “smarter” based on IQ scores over the past 85 years. This is a good book if you are skeptical when you hear people say “things are so bad these days…”

31. Infidel by Ayaan Hirsi 
 To say this story was eye-opening and powerful would be an understatement. Ayaan chronicles her path growing up in Africa as a Muslim and how that shaped her role as a woman in the world. Her journey is long on challenges but also long on courage and it was inspirational to read a book from such a powerful woman.

32. The ONE Thing by Gary Keller
If you are excited by pursuing a path that excites you, interested in optimizing your mental performance and asking yourself the tough questions, this book is for you. This book dispels some myths around productivity (hint: your to-do list is not aligned with your success), willpower and discipline. Recommended by a mentor I respect, this book has helped me focus my time on both the things I am good at and the ones that give me energy.

What's the most influential book you've read?

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