Books that have changed my life [2012-2018]

I try to read a lot. I find it valuable to change my perspective, teach me new things, or simply for entertainment value. The following are books that, whether by content or by chance, taught me something that has stuck or changed my approach to life. In order to be included in this list, the book has to have fundamentally altered something about the way I see the world.

I wrote a version of this post a while back. I’m going to skip repeating the books on that list, but they’re still good.



The Art of Learning by Josh Waitzkin. I read this a long time ago, but it helped kick off a reinvigoration of learning for me. This book and both of the Tim Ferriss podcasts with Josh Waitzkin, gave me a huge appreciation for the importance of learning to use the subconscious as an ally for learning and working. It also encouraged me to see being bad at new skills as simply “Investing in Loss” as Josh calls it in the book. I’ve tried to do much of that since reading this book, in chess, drawing, writing, flying trapeze, tango, etc.

A Mind for Numbers by Barbara Oakley. Holy shit. If you want to be better at learning, read this book. Maybe I was just bad at it before, but the ideas and techniques in this book have changed my approach to learning everything, from coding concepts to memorizing music. I’m really grateful to have stumbled across it. I owe that to Derek Siver’s summary of the book.



Positive Intelligence by Shirzad Charmine. I read this with a book group, and we all came in to our next meeting feeling like this book had opened a new realm of observation. Shirzad talks about our Judges, or the ways we cut ourselves down and hold ourselves back. He gives them archetypes and enough detail to start observing and weakening them. This book led me down a path of learning to meditate and investing in therapy, both of which have had lots of positive side effects. I’ve recommended this book to many people whom I hoped would see the same benefits as I did.

His concept of Positivity Quotient for teams has also stuck with me. I frequently refer to it when evaluating how I’m doing in my job.

Nudge by Cass Sunstein and Richard Thaler. I’ve read a lot of books on behavioral economics, so this one is somewhat representative of a whole class of books, but it is great in and of itself also. It’s somewhat long and dry, but it really helped me gain perspective on both decisions I make as a person and product design choices I make at work.



Radical Candor by Kim Scott. This book is all over the place in Silicon Valley (including the TV show), but for a good reason. It’s a remarkably simple framework which helped me identify one of my primary weaknesses as a manager (I tend towards ruinous empathy if I’m not careful). It then offers a number of helpful tactical ideas that I have adapted into my work.

Peopleware by Tim DeMarco. This book is full of little tidbits for people who manage software teams, like learning about the Hawthorne Effect as it applies to process change or the concept of Teamicide.

Team of Teams by Stanley McChrystal. The ideas that: 1) efficient process creates brittleness and rigidity and 2) forming human relationships across organizational boundaries has massive benefits have changed how I look at organizations and management.

Runner Up:

Extreme Ownership by Jocko Willink and Leif Babin. This book was a great reminder to own outcomes and not make excuses. I’d recommend this book for the value of this alone. Jocko is also a force of nature and his podcast is interesting perspective and inspiration at times.


Sapiens by Yuval Harari. The biggest thing I got from this book was the realization that nearly everything we do as humans is based on shared ideologies. Much of what we take for granted could very well be shared illusion or confusion.

Leonardo da Vinci by Walter Isaacson. This book has made me way more excited about filing my notebooks with all sorts of things. Kind of an odd take away, but learning about Leonardo’s curiosity and endless search for discovery and answers was invigorating and led me to keep trying to go deep into new subjects. Also, discovering how bad he was at finishing things made me feel better about not pushing every project I start to completion



Interestingly, in compiling this list, I realized how many books I’ve read that didn’t have this effect. I feel like I’ve been getting more and more picky these days about my reading, especially for non-fiction. I mostly feel like I’ve gotten about everything I can from self-help books and management books. I still occasionally will be surprised by something in these categories, but have been exploring more history, art, and fiction recently, which has been fun.

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