Over the last few years, I've read 20-40 books each year. Some were throwaway works, while others made a lasting impression and I've given away copies to friends. I think that books are still one of the best ways to communicate complex ideas and to engage with some of the best insights of history, so I want to share some of the things that colored how I think about the world. (If you know the inputs, you can guess the outputs, no?)
That said, I also want to recognize a certain myopia the lends to the list being full old white men. While I can't change the past, the future is yet unwritten – and most importantly, still unread.
Nonfiction - Technical
This is the book that got me into computers. Dense but fascinating story of the birth of electronic computers (the hardware of it all) and how the big/fundamental software problems have not changed at all.
The Information: A History, A Theory, A Flood
by James Gleick
This is the "software" companion to Dyson's "Turing's Cathedral". Illuminating. Claude Shannon's impact on information theory helped me understand so much about technology.
Incerto Series (Antifragile, Skin in the Game in particular)
Nassim Nicolas Taleb
Pugnacious, counterintuitive, and persuasive. Where ethics, statistics, and decision theory intersect.
The Theory That Would Not Die
A whole nonfiction narrative about Bayesian statistics? Actually fascinating.
More of a pamphlet than a book, but an essential research companion guide to how to work with data & its human side.
The Phoenix Project
Gene Kim, Kevin Behr, George Spafford
There's a lot that I learned from this novelization of how IT departments function & produce work, and was given so many threads to pull on for further reading.
Nonfiction - General Interest
Guns, Germs, Steel
I think this was the Sapiens of the 2000s? There were a few big ideas here, beautifully narrated.
Change by Design
It's hard to capture the formative learnings of your college days, but when I was at Parsons, design thinking was the thing that was being taught. As students we were a few years ahead of the curve, and Tim Brown's book captured a lot of the ways of 'thinking about problems' that we were studying. I never actually finished the book, but only because it was too close to home at the time.
Thinking in an Emergency
Elaine Scarry is brilliant and this plus "The Body in Pain" are both great explorations of their topics. I like to think of "Thinking in an Emergency" as a deeper, more robust, and more practical "Checklist Manifesto".
About how people come together. Short, sweet, and utterly fascinating. When I finished it, I went back to page one to reread it and take notes.
I think this book colored my perspective on organizational behavior & the malfunction of well (or nigh) intentioned systems. Utterly fascinating for anyone who works at a large corporation, or wants to understand a very particular human element of American capitalism.
I don't think I'll ever forget the evocative distinction between privacy and secrecy: 'everyone take a shit; it's not a secretive act, but it is one that most of us want privacy for.'
A Universal History of the Destruction of Books
An insanely morbid account of all of the knowledge lost throughout history due to book burnings and library destructions, for all sorts of reasons. Read it and cry.
Cult Fiction Anthology
A canon of fiction authors, their books, and their lives. A small book, I carried it in my pocket for years as a how-to for getting an alternative literary education.
I could put almost anything by Jan Chipchase here, but this one stuck with me for a while. More of a subversive case study than a book. I think you can read it here as a series of blog posts.
A fascinating history of the evolution of the corporation through history, and the long running tension between business (commerce) and government.
Regardless of how you feel about Kissinger-the-man, this was a fascinating exploration of China's history and evolution of its modern political philosophy from a guy that was deeply intertwined in its history. I learned so much from this book, and think that anyone who read it has not been surprised by the last decade of China's actions.
Team of Rivals
Doris Kearns Goodwin
Almost a cliche to say that if you want to understand politics and working together across the aisle you should read this, but this was a fascinating biography of Lincoln and a masterclass in working with people.
Better known as the inspiration for the musical, but Hamilton was a really brilliant thinker and the sections on designing government and policy were fascinating. I sometimes think I learn more about 'how things work' from biographies than I do from dry explainers. Detail & context is everything.
Ride of a Lifetime
I usually on recommend books a few years old, but I read this and them immediately found myself turning to it over and over again for some of the insights. His perspective on presenting to the board helped me craft & pitch my marketing plan when I started a new role. His perspective on negotiation and working with people helped guide a lot of early conversations with folks who were personally invested in some of their successes. Anyway, a masterclass in business and the impact of being thoughtful when working with people. There's a lot to criticize about Disney, but also a lot to learn about business leadership from Bob Iger.
Love him or hate him, hard to deny the chutzpah, technical vision, and impact on our world by nearly sheer force of will. Musk lives his own quote of "eating glass and staring into the abyss".
Boyd: The Fighter Pilot Who Changed the Art of War
Boyd sometimes feels like one of the best secrets out there. His impact on strategic thinking and modern military design cannot be underestimated.
I know very little about football, and care even less. Yet this book on Bill Bellechik, coach of the Patriots, was a masterful lesson in management, recruiting, and chock full of insights of managing teams. I took copious notes every chapter.
Jonathan Safran Foer
Single-handedly the reason I became a vegetarian.
Born to Run
Single-handedly the reason I started running.
Nonfiction - Philosophy
Existentialism is a Humanism
Jean Paul Sartre
The shortest, most accessible, most direct of Sartre's work. I come back to its intentionality even today.
I think this came out as a series of New York Times essays originally. I remember printing them out and reading them. About Thomas Khun, his paradigm shifts, and self-blindness, among other things.
Duty of Genius: Wittgenstein
I find biographies to be really helpful in contextualizing a person's work. It's easier to follow the steps to a conclusion than to start with the conclusions themselves. Ludvig Wittgenstein impacted how I think about the world for a good decade, and impacted how the world thinks about philosophy for a good hundred years.
Two Cheers for Anarchism and Seeing Like a State
James C. Scott
Two sides of the same coin – one a deep academic review of the failures of state planning, the other a celebration of political anarchism (and not the punks-burning-things kind).
Dunne & Raby
A ramble through the intersection of maker culture, design, and science fiction. Not really a philosophy book.
Ego is the Enemy
What an interesting character. I read his "Trust Me, I'm Lying" when I was first getting started in marketing, and stuck around for his reading lists. This book is a turn to stoicism, the middle part of a 3-book trilogy ("Stillness is the Key" and "The Obstacle is the Way" are the other two). This one resonated with me the most, probably because I need to take myself down a peg or two every so often. It's not a good book in the sense that it can often read like a collection of quotes, linked together with some narrative, but it was right at the time and I took a lot away from it, recommended it to others, and they got a lot from it too.
All Quiet on the Western Front
Erich Maria Remarque
Jean Paul Sartre
I wouldn't recommend it but I read it when I was 13 and came out changed.
Blue Ant Trilogy
I think I stayed in marketing for the better part of a decade because of the imprint that these books made on me when I first read them.
That jackpot. Those peripherals.
China Mountain Zhang
It's a science fiction book about common people – just living your life and the small everyday struggles – homosexuality, immigration, education, certification, finding a job, playing games. A beautiful book that feels like a path for what science fiction could be, a path not traveled.
Anything by Philip K Dick.
The Hainish Cycle (particularly The Dispossessed, Left Hand of Darkness)
Ursula K Leguin
Feminist, politically science fiction years beyond what anyone else was writing, using the lens of "some things different" to explore themes very dear to our times.
The book that inspired me to learn about computer engineering. Also, its really good.
The Savage Detectives
A giant of South American literary fiction alongside Cortazar, Borges, and Garcia Marques... but perhaps the one with the most youthful energy, full of love and action and an absurd by comedic amount of self-seriousness.
A classic for a reason. Tolstoy's books are set in history, but what they explore are relationships between people and how folks act, feel, and think – things that in both our petty and noble natures do not change. There's no better, more expansive way to explore that than a long stroll through Tolstoy's books.