Books I Enjoyed In 2016

Drew Dillon
ProductMan
Published in
7 min readJan 2, 2017

In 2016, I resolved to focus on learning. I found mentors in fields I’d never worked in before and read as much as I could. All told, I read 37 books last year. Here are 19 of my favorites from the year and what I learned.

The End of Average Rose, Todd
Much of my reading this year took aim at the Taylorist view of the world, but most would just devote a chapter. Todd goes a hundred steps further, giving a history of the concept of average before elucidating the many ways the shorthand of “average” negatively impacts our lives.

A Book of Five Rings Musashi, Miyamoto
If you learn nothing else from Miyamoto, it’s the importance of hard work and practice. He not only outlines the elements of a philosophy that allow a single swordmaster to take on thousands, but continually reinforces how hard it will be for you to understand and live that philosophy.

If you master the principles of sword-fencing, when you freely beat one man, you beat any man in the world. The spirit of defeating a man is the same for ten million men.

You should consider this deeply.

Made to Stick Heath, Chip
Clarity of communication was a big theme for me early in the year. How do you distill a message to it’s essential elements and make it memorable for the people you’re communicating that message to?

One thing that stuck with me was the weakness of abstraction. That experts in a subject must fight to make their messages more concrete. There’s a clear connection from here to Nassim Taleb’s work below.

NeuroTribes Silberman, Steve
One of my favorite books of the year was this history of autism. Silberman gives a detailed account, from the earliest records he can find, of people exhibiting autistic traits. Indicating that autism isn’t a recent phenomenon, brought on by some fault of modern living. He traces its diagnosis and the search for a “cure” through the eugenic movement, exercised ruthlessly by the Nazis, and into the modern era.

The takeaway, like The End of Average and so many other things I read this year, is that we shouldn’t be trying to fit everyone into the same box. Autistic kids have very different needs in terms of schooling and socialization, but that that investment is worth it. That science and humanity need people who question authority and may focus on narrow things that others overlook.

The Industries of the Future Ross, Alec J.
I heard an interview with Ross partway through the year and was impressed. I had no idea the State Department interacted with other countries in the ways he was describing.

During this part of the year, I was thinking a lot about innovation. Where do great ideas come from? What do they need to survive?
Ross has interesting ideas here, like Japan becoming a robotics hub, due to labor shortages, etc.

Fooled by Randomness Taleb, Nassim Nicholas
I never read Taleb’s more popular Black Swan, honestly I thought it was written by Malcolm Gladwell and steered clear. Fooled by Randomness popped up in a blog post about VCs’ favorite books and I hadn’t heard of it or the author, so I checked it out.

Taleb treads familiar ground in this book, that people suck at understanding probability, but layers it with his own reading in philosophy and experience as a stock trader. What you come away with is a lot of refreshing and contrarian views to life and risk taking.

Antifragile Taleb, Nassim Nicholas
Taleb asserts that small amounts of stress and failure toughen, rather than weaken, organic things. Attempts to prevent those stresses and small failures lead to catastrophic failures.

Taleb gets a lot deeper into his personal philosophy in this book, down to his diet and exercise routine. Taleb is a great contrarian and this book is basically a catalog of counternarratives, some even contradicting other parts of the book. I could see why people who don’t like their beliefs challenged might not like this book, but I really enjoyed it.

The Life-Changing Magic of Tidying Up Kondo, Marie
I admit, I read this one for the hype and for the giggle factor of telling my wife I was reading it. But, as cleanliness challenged as I am, I have to admit a deep love of throwing crap away.

I didn’t Konmari the whole house the next week, but I did use this as a nudge to get rid of a lot of clutter and have been more mindful about the things I bring into the house since.

Work Rules! Bock, Laszlo
I sell software to HR, so it made sense to me to look at Google’s innovative approach to HR. Bock’s HR department certainly wasn’t typical, with data folks and former consultants making up 2/3rds of the team.

The book was a bit rah-rah Google, but I appreciated his drive to prove the efficacy of the programs he put in place. I also saw parallels with Ed Catmull’s work at Pixar in terms of refining and implementing new ideas.

This Will Make You Smarter Brockman, John
This isn’t one book, but rather a collection of essays. Many are futuristic and/or thought provoking, but a few are summaries of the work of Daniel Kahneman, et al.

The Alliance Hoffman, Reid
Halfway through the year, I read a number of books on leadership. I’m not sure why, maybe my natural dislike of business books, but only one made the recommendations list for me.

Hoffman outlines a pretty simple management practice wherein employment is viewed as tours of duty. These tours are mutually agreed upon to make sure the employee grows in the way that they want and the company gets what they need from that employee. I found this and the detailed sub-recommendations to be a useful tool for myself and the managers on my team.

Sapiens Harari, Yuval Noah
Harari’s book, deservedly, made a number of top 10 lists this year. It’s a thought-provoking exploration of what it means to be human. The good and bad of our evolutionary past and the implications for our future.

The memory I still carry from this book was Harari referring to forms of government, capitalism, etc. as forms of religion. This rang true for me and still has me considering the belief and the responsibilities of government.

Creativity, Inc. Catmull, Ed
Another book about innovation, this time from one of the co-founders of Pixar.

The history of Pixar alone makes for a pretty fun read, but Catmull also discuss the ways Pixar has worked to gather and cross-pollinate ideas from across the company. This is an area anyone who works on products must strive to improve.

I think product people will find parallels with a director of Pixar, whose story about princes living in the clouds may become one about a senior citizen flying his house to South America.

Between the World and Me Coates, Ta-Nehisi
Coates’s book is, for me, a competitor for favorite books of all time.

Written as a letter to his son, Coates tells the story of his education. That black people in America don’t have ownership of their bodies. That the n-word is an abstraction for hate of the mistreated anywhere. And that only by eliminating this concept can any of us be free.

It probably shouldn’t have been as eye-opening as it was, but this book deeply affected me. I’m still considering what I can do about it.

The Happiness Advantage Achor, Shawn
Achor’s book was one of the first I read this year. My goals in reading it were twofold:

  1. Learn more about what makes people happy at work, part of AnyPerk’s mission.
  2. Learn more about motivation and how to make my employees feel more fulfilled in their work.

I enjoyed Achor’s model and especially the connections to innovation, another area of my research.

I summarized Catmull’s book and Achor’s in a presentation to my team about mindset and innovation. A few months later, an employee admitted to me that he’d been having a tough time personally and was considering quitting, but that the presentation had struck a chord with him and kept him at the company.

Re-Reads

It had also been a long time since I read a few books that I discuss frequently. I decided that a renewed focus on learning should include going back to a few books to see if they have anything to teach me now, later in my career.

The Lean Startup Ries, Eric
This is one of those books that gets half-quoted so often, it loses all meaning.

The last time I read Ries’s book, I was an individual contributor at a mid-sized company. Reading it now as an exec at a small company, it was a different experience. I can now impact these things at my company and it lead me to deeply consider and socialize whether we had sufficiently prioritized validated learning.

Thinking, Fast and Slow Kahneman, Daniel
The seminal work on bias and foundations of behavioral economics. Kahneman and his partner Amos Tversky researched decision-making and its relationship to the structure of the human brain.

Kahneman is referenced in 2/3rds of the books above and this book should be required reading in high school, if not sooner.

Predictably Irrational Ariely, Dan
Ariely continues the work of Kahneman, outlining many ways in which our brains cause us to make poor decisions. I learn something new each time I read this book, as my own perspectives and recent decisions change.

Honorable Mention

The Death and Life of Great American Cities Jacobs, Jane
This is an incredible book, outlining the philosophies of city planning and their failures. Jacob’s book discusses the technical details of what makes a vibrant city block or park, and how to achieve them. Unsurprisingly, Taleb references her work in Antifragile.

The only reason I don’t recommend the book at the top level is that it’s dense. Late in the book, she goes into some pretty extreme detail that might not be relevant to cities today. But other than that it’s great.

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