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Infidel by Ayaan Hirsi Ali (10/10): This book is gripping, dark, scary and inspiring. I find her to be one of the bravest women alive. Definitely check it out.

The Autobiography of Benjamin Franklin by Benjamin Franklin himself (7/10): This book is fascinating mostly because its his own narrative about his life. I found the part about how he manually tracked his virtues over a number of weeks in a chart. The OG life hacker.

Chaos Theory & Complexity

Chaos by James Gleick (unrated): I remember reading this senior year of college and being captivated by Fractals. I've read it too long ago to give it a serious review, but I remember it was a challenging read.

Chaos At Work by Paul Millerd (unrated): This is an essay in which I try to map some of the (mostly missed) lessons of Chaos theory to modern organizations.

Riding On The Edge Of Chaos (MIT Management Review) by Richard Pascale (10/10): This essay combines a nice narrative of an organization embracing the principles of chaos theory as well as an exploration of the science. Fun read for nerds.

Community & Connection

Tribe: On Homecoming and Belonging by Sebastien Junger (10/10): This short but powerful book contrasts Junger's experience in war and coming back home trying to fit into modern society. He explores the modern world's loss of community, connection and belonging.

The Unsettling of America by Wendell Berry (9/10): Wendell Berry tries to make sense of the systematic shift away from farming as a local family-driven endeavor to one done by major industrial organizations. This book is a fascinating combination of diatribe on farm policy of the 1970s (don't worry you can skim through quickly) combined with relationships, work, love, marriage, community, belonging, food and connection to nature.

Creativity, Curiosity & Originality

Curiosity by Ian Leslie (9/10): Leslie walks us through three types of curiosity: empathic, diversive and epistemic. He also explores the history of curiosity (Saint Augustine described it as "pointless, perverted and prideful) as well as some of the modern beliefs around education and what people miss (general knowledge does matter)

Originals by Adam Grant (My Graphical Book Review) (10/10): Originals is probably one of the best popular books to understand modern organizations from a lens of creativity and originality (and why it doesn't happen). He shines light on why middle managers often don't take risks and looks at inventors like Edison and Einstein went through enormous amounts of duds before landing on some great ideas.

The Icarus Deception by Seth Godin (9/10): Godin challenges the convention takeaway of the Icarus myth to "not fly too close to the sun" and says instead: ""we tend to forget that Icarus was also warned not to fly too low, because seawater would ruin the lift in his wings. Flying too low is even more dangerous than flying too high, because it feels deceptively safe." He packs a ton of personal "case studies" or stories of people that harnesses their creativity.

Freelancing & Self-Employment

Linchpin: Are You Indispensable? by Seth Godin (10/10): Godin has been a self-employed solopreneur and freelancer for decades. He helps people re-frame their thinking away from needing to be “chosen” for a job towards a world where the world depends on you expressing your creativity and daring to “make a ruckus.”

Gig Economy, Diane Mulcahy (5/10): Probably a 5 for experienced freelancers, but a 10 for people without any knowledge or experience with the gig economy. Has a bunch of great exercises for helping people think about how to figure out what to focus on and how to position yourself in the freelance economy,


A Random Walk Down Wall Street by Burton Malkiel (10/10): Finance is one of the things that gives people enormous anxiety, yet they want to exert zero effort to ever understanding how money actually works. Investing is quite easy if you are willing to learn and have a guide like Malkiel. 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. This book should be required reading for all college graduates.

Gift Economy & New Economic Models

Sacred Economics: Money, Gift, and Society in the Age of Transitionby Charles Eisenstein (10/10): This was a mind-altering book where Eisenstein combines his academia chops and deep understanding of economics with a re-imagination of what is possible if we questioned "why" behind some of the ways our economy is set up. Reading this book inspired me to experiment with a gift economy approach in my work, which has been amazing.

+ Linchpin also touches on the idea of a gift economy


Happiness Hypothesis: Finding Modern Truth In Ancient Wisdom by Jonathan Haidt (9/10): This book is an amazing walk through history ans the wisdom of our elders and what they knew about happiness. It seems that in the busyness of the modern age, we have forgotten a lot of these lessons.

The Happiness Advantage by Shawn Achor (8/10): Another book about happiness from someone that lived with Harvard undergraduates. One of the key takeaways from this was that the people that took breaks and spent time with friends when they were stressed seemed to do better in school and other achievements than the ones that powered through with the work.

Health & Food

The Omnivore’s Dilemma, by Michael Pollan (10/10): I felt a bit dumb after reading this book. How could I be eating food created by the monster that is the US Industrial Food system and not know what is happening to my food. I learned about grass fed vs. grain fed meat, what factory farming is doing to the quality of our food and soil and how we are disconnected from how we get our food. Most of all this just woke me up to pay attention to what I'm actually eating.

Introversion / Solitude

Quiet by Susan Cain (10/10): 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.

Solitude & Leadership by William Deresiewicz (10/10): I try to read this essay once a year. What seems like an ordinary college graduation speech comes off as a call for a deeper sense of leadership. The kind not build on heroic action and achievement, but the kind built on a foundation of reflection, solitude & friendship.

Learning, Thinking & Mental Models

American Scholar (Essay) by Ralph Waldo Emerson (9/10): This timeless essay talks about the state of learning in the 1800s and still rings true to the limits of learning in institutions today.

The book, the college, the school of art, the institution of any kind, stop with some past utterance of genius. This is good, say they,—let us hold by this. They pin me down. They look backward and not forward. But genius always looks forward. The eyes of man are set in his forehead, not in his hindhead. Man hopes.

The Art Of Learning by Josh Waitzkin (10/10): 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.

Antifragile by Nassim Taleb (10/10): 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.

Skin in The Game by Nassim Taleb (9/10): Not as good as Antifragile, but a book about a simple and powerful idea. His argument is that for systems to survive, we need "skin in the game" which means that there needs to be some cost tied to actions within the system. You cannot have a system where individual elements survive no matter the failure (e.g. too big to fail banks). Written with Taleb's usual charm :-)

Freakonomics by Levitt & Dubner (7 or 10/10): This book gets a 10/10 because it is one of the first books that really awakened my curious mind when I was about 20. 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. I'd probably recommend Predictably Irrational instead of this book now.

Predictably Irrational by Dan Ariely (9/10) Highly entertaining read if you like to have your ideas of conventional wisdom be shattered. Many of the experiments were done in my favorite grad school bar (Beacon Hill Pub). This book was one of the first that led me on a path to accept that we are all irrational. The rational "economic" 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

A Lesson on Elementary Worldly Wisdom As It Relates To Investment Management & Business by Charlie Munger (10/10): Everyone should read this speech at least once in their lives. I've read it a few times. Although we are clearly irrational as the book above says, there is still room for embracing new mental models, especially if they help you re-frame what is happening or consider alternatives as part of a decision making process.  Munger is probably one of the best in the world at this and this speech will show you why.

Moonwalking with Einstein: The Art and Science of Remembering Everything Joshua Foer (8/10): 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.

The Signal and the Noise, Nate Silver (8/10): 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.

Everything Bad is Good for You by Steven Johnson (7/10): Today's reality shows are way worse than what was on TV 50 years ago, right?  Wrong.  Johnson argues that if we are going to make comparisons, we need to compare our worst media today with our worst media 50 years and and same with the best media.  Game of Thrones is a much more demanding show to watch than I Love Lucy.  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…”

Meaning & What Matters

Survival In Auschwitz by Primo Levi (10/10): This was a powerful book that ponders what is means to survive in one of the darkest moments in human history. Quotes like this one were a slap in the face to any modern worries I might have: "Sooner or later in life everyone discovers that perfect happiness is unrealizable, but there are few who pause to consider the antithesis: that perfect unhappiness is equally unattainable."

Man's Search For Meaning by Viktor Frankl (10/10): I think everyone should read a story about someone's experience in the holocaust at least once in their lives. Levi or Frankl's books are both perspective-shifting. This book tends to drift into his own personal philosophy called "Logotherapy" but I think most people will resonate with the general sentiment offered here:

Everything can be taken from a man but one thing: the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.

Tuesday's With Morrie by Mitch Albom (10/10): Every time I read this book I end up crying because Morrie is very much a man I deeply admire. I first 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. 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.

Last Lecture by Randy Pausch (10/10): Continuing in the same vein as Morrie, this book is literally the last lecture given by Professor Pausch. His topic is reconnecting with your childhood dreams. It is originally based on this lecture (here's the video), though I think the books is a bit cooler. If this doesn’t move you to tears, I don’t know what will.

How Will You Measure Your Life by Clayton Christensen (9/10): 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. (alternative: check out the longform version here)

Philosophy Of Work

Modern Organizations

Sociology of Drug Culture & Economics

Persuasion & Communication

Philosophy Overviews

Mindfulness, Rest & Spirituality

Understanding Politics

Mastery & Performance

Life Design

Travel / Nomadism