At the start of 2017 I, feeling a little unproductive, defined a set of goals which I’d try to achieve by the end of the year. It was around this time that I, feeling a little unhappy in my job, started looking at other places to work. While I was investigating the culture and history of Stripe (which I ultimately joined) one very common theme was how voracious of a reader its CEO Patrick was.

Reflecting on the meager list of books I’d completed in 2016, I realized that my own reading pace had dwindled over the years. Back when I commuted to Mountain View from SF, I generally had multiple hours per day to read. That became maybe 40 minutes each day when I started taking Muni to work downtown. When Twitter moved its office to within walking distance I basically stopped entirely, not making up in reading the time I was gaining from a shorter commute. I missed the depth I felt that I got from reading books and figured the best way to bring that back was to construct a goal of reading a specific quantity this year.

I had only read a handful of books in 2016 so I figured that even one a month would be a reasonable improvement. I rounded that up to 15 (stretch goals!) and actually wound up starting and finishing 17 books in 2017, a great success!

This late in the year I tend to feel reflective, so I thought I’d write a little bit about what I read, why I picked it, and what I got out of each book. These are listed below, roughly in order of completion:

Eccentric Orbits: The Iridium Story by John Bloom

During my interview process at Stripe I got the chance to have a brief chat with Patrick over the phone. I asked him what he was currently reading and he said something like “I’m reading a book called Experimental Conversations, but you shouldn’t read that, you should read a book called Eccentric Orbits”. I wish I remembered how he sold it but it was something along the lines of the story of building the Iridium satellite cluster being ‘a triumph of the corporate system’.

Iridium is the network which powers those satellite phones you see in movies like Jurassic Park 3 and American Sniper. The cluster itself is a spinning matrix of planes of orbiting satellites and has some roots in the Star Wars missile defense from the 1980s. The technical background and challenges in getting dozens of satellites into orbit made for a great story. But the bureaucratic mess involved with funding and coordinating all of this was surprisingly fascinating too. Structuring a business with such huge upfront costs both in terms of regulation and financing is extraordinarily difficult and it’s kind of amazing that such projects actually happen. Not without costs—the first company to run Iridium went bankrupt. But the book covers the process of salvaging what remained and structuring a successful business off of that. It was a great example of second-mover advantage which I’ve come back to many times this year.

Iridium continues to be topical in 2017. The next generation constellation is being launched by SpaceX and recently passed the halfway point in deployment.

Blue Mars by Kim Stanley Robinson

I only read a few books in 2016 but I did finish the first two books of the amazing Mars Trilogy. Covering the colonization, development, and terraforming of Mars, the trilogy seems especially pertinent as we get closer to the first manned mission to Mars. I felt that the series went on a little long but the third book closed things out with a huge scope and an impressive examination of the way that future technology can shape civilization.

One of the most terrifyingly prescient parts of this series was a description of massive sea level rise due to the collapse of Antarctica’s west ice shelf. This sends Earth into chaos and prompts a surge in immigration to Mars. This description was originally published in 1994 but the New York Times’ amazing reporting on Antarctica this year highlighted how realistic that threat is to our future society.

Experimental Conversations: Perspectives on Randomized Trials in Development Economics by Timothy N Ogden

I figured I’d check out the other book Patrick mentioned during our call, so I read this series of interviews with economists about their use and perspectives on randomized trials for economic studies. It was a bit out of my comfort zone and I didn’t have background on many of the studies referenced. In that sense I learned a few things, for example how in this paper by Pascaline Dupas and Jonathan Robinson simply providing Kenyans a physical box to put money into helped facilitate savings:

Our most striking result is that getting access to a safe and designated storage technology as simple as a Safe Box can have large and lasting impacts on health savings and investment behavior. How is this possible? All the Safe Box provided was some protection against theft, but in focus groups conducted before starting the study, theft did not seem to be a primary concern for people. What then accounts for the large impact of the Safe Box? This section presents evidence from open-ended survey questions that we administered to our study participants throughout the study period. All in all, the data strongly suggests that the box facilitated labeling, which, as discussed in Section II, is a form of mental accounting that can act as a commitment device: once money was put into the box, it was labeled as health savings, which made it less fungible and therefore less susceptible to friends’ requests and daily spending.

Payments Systems in the U.S. by Carol Coye Benson

Upon joining Stripe, new hires are given a copy of this book. It’s (supposedly) a little dated given the fast paced world of payments systems but I found it a nice quick overview of some general banking concepts and terminology.

The Well-Grounded Rubyist by David A. Black

In the spirit of preparing for my new job at Stripe, I knew that I’d need to brush up on Ruby, which I hadn’t written professionally for several years. This was a well-scoped overview of the mechanics of the language and helped me understand some unique concepts to Ruby which I hadn’t really gone too far into previously. I recommend this book to new hires who haven’t written Ruby in a while.

Shoe Dog by Phil Knight

This is another Patrick book. I’ll admit that his recommendations are prevalent in this list, but there’s some kind of survival bias going on here where he reads a lot, therefore he recommends a lot, therefore many of the recommendations I receive come from him. In this case I think he was presenting at an all-hands meeting and said something like “if you want to understand how important cash flow is to a business, I recommend reading Shoe Dog”.

Indeed, I felt like I came out of reading this book with an appreciation for how important (and how much of a gamble) contributing profits back into a company for growth and expansion is. It worked out well for Nike and Amazon but from this account managing cash flow seems like a tough needle to thread.

Distributed Algorithms: An Intuitive Approach by Wan Fokkink

When I started at Stripe, I joined a weekly paper reading group which focused on academic Computer Science papers. Most of these were for distributed algorithms, implementations of which I had worked with at Twitter but were new enough that I hadn’t studied them in the course of obtaining my C.S. degree. This overview of distributed algorithms had a great depth of coverage and was presented in a practical way without getting too far into specific proofs.

The Rise and Fall of D.O.D.O. by Neal Stephenson

I have a weakness for Neal Stephenson books. I’ve read all of his books at least once, including those published under pseudonyms. So whenever a new one comes out it jumps to the head of my queue.

There seem to be a couple archetypes of Stephenson books. There are (1) fully plotted, fleshed out worlds like Snow Crash, Cryptonomicon, the Baroque Cycle, and Anathem. Then there’s the (2) “good idea but more of a sketch” novels such as Reamde and Seveneves. Then the (3) “several credited authors and it feels like Stephenson wrote maybe three chapters” books: The Cobweb, Interface, The Mongoliad. To be clear I enjoy all of them, but this fell somewhere in-between 2 and 3, while 2015’s Seveneves was closer to being somewhere between 1 and 2. That being said, the story which intertwines witchcraft, technology and time travel is an entertaining read.

Multipliers: How the Best Leaders Make Everyone Smarter by Liz Wiseman

I started managing the Subscriptions team at Stripe in October, which was more than six months since I stopped managing a team at Twitter. So I brushed up the sources I mentioned in Reading List - Managing Engineers and decided to go more into depth on Liz Wiseman’s Multipliers framework. This gave me plenty of areas to work on as I got back into managing again.

Managing Humans: Biting and Humorous Tales of a Software Engineering Manager by Michael Lopp

In the same vein as Multipliers, I read the book version of the Rands in Repose blog. I’ll be honest that this provided only a little additional information over the posts I had already read. I’d strongly recommend this book if you’re a manager and haven’t read the blog, but you can skip it if you have.

Color and Light: A Guide for the Realist Painter by James Gurney

I spent 2017 trying to paint regularly. I’d been following James Gurney’s incredible art via his blog and Instagram feed but was excited that he had published a few books on art theory. This book helped inform my understanding of light in my own paintings and gave me lots of techniques to look for when analyzing art. Looking back at the master studies I completed in January, I see why many of those paintings “worked” while many of my own imaginative paintings didn’t. It’s also a very fun book to read as it contains a bunch of wonderful examples from James’ own portfolio.

All the Birds in the Sky by Charlie Jane Anders

Back when Gawker was still a thing, I read io9 pretty regularly. I remember noting the editor Charlie Jane Anders’ posts as being well-written, so when I found out that her first speculative fiction book was nominated for the 2017 Hugo award, I added it to my list. Despite feeling a bit twee to start, it evolved quickly and I found myself pretty impressed with the places the story went. In a weird theme, this was the second witchcraft/technology crossover book I read this year and probably the better one of the two. Anders’ style evokes Matt Ruff, one of my favorite authors, and I’ll be happy to read more of her work.

Powerhouse: The Untold Story of Hollywood’s Creative Artists Agency by James Andrew Miller

Another Patrick book. This time it was referenced with regard to this article comparing the opportunities given janitors at Kodak in the 1980s vs. Apple today. The Creative Artists Agency had a habit of breaking in its junior employees in the mailroom and giving them opportunities to prove themselves before rising to the prestigious (and well paid!) heights of being a full agent.

There were lots of notable points in this book, but I especially liked the structure, which was told almost entirely via interview quotes. The story is told verbatim from words of the founding team, agents who worked at CAA, and many of their famous clients. Yet it maintains a narrative thread and I always understood the points it was implying through editing. Like an Errol Morris documentary, the mastery is in the editing.

Spelunky by Derek Yu

I actually re-read this in 2017 after telling a few people it was my favorite book about product development. Derek gives a really unique and deep insights into his creative process while developing Spelunky. It may seem very game-specific but the things I loved about that book are broadly applicable to many things I do: How to structure a creative process in a rigorous way. Evolving a product and learning about its strengths through iteration. Acknowledging that making games is more fun than programming and choosing tools that favor making games rather than programming more. Finishing and practicing finishing. I have a very high highlight to word count ratio on this book.

Jagged Alliance 2 by Darius Kazemi

This book is in the same series as Spelunky and covers a strategy game which I loved in my youth. Darius doesn’t bring the same creator point-of-view to his investigation as Derek did, but he does a great job of picking apart the systems of Jagged Alliance 2, giving a good analytical breakdown of the interactions which led toward the game’s unique strategy and sense of identity.

Groundwork for the Metaphysics of Morals by Immanuel Kant

One of the most pleasant surprises on TV in recent memory has been The Good Place. It’s a really well-crafted show and manages to keep things interesting without being too convoluted. It also makes philosophical concepts a bit more accessible and I found myself wanting to read more about morals after watching the show. So I picked up one of the references and started reading Kant.

I’ll be honest that it’s been a while since I read any philosophy and it was harder to get through than I’m happy to admit. My process was essentially to read a section of the book, then the corresponding Wikipedia summary to make sure that I understood the gist. It was interesting to follow Kant’s derivation of his categorical imperative: “I ought never to act except in such a way that I could also will that my maxim should become a universal law”.

Death’s End by Liu Cixin

The other series I read in 2016 was Remembrance of Earth’s Past, beginning with The Three-Body Problem and followed up with The Dark Forest. I finished the series in 2017 and it’s still lingering there in the back of my head. Cixin has this amazing ability to manipulate the emotional impact of his scenes, and I find myself oscillating between wonderment and despair throughout. The scale he deals with is incredible, and his ability to provide a seamless ladder of technological leaps from present day up to the end of time itself easily matches the abilities of Stephenson and Robinson whom I also read this year. This particular book deals with many dimensions and presents an immensely convoluted subject in a wonderfully illustrative way, evocative of the iconic Flatland. The final sequences in the book are absolutely haunting.

And that’s it! One of the few goals this year I was able to surpass, which means that I can set a more ambitious target in 2018.