I enjoyed publishing some thoughts on my reading list from 2017 at the end of last year, and wanted to continue the tradition in 2018. I think my blend moved more toward nonfiction this year, which I’ll blame on getting a ton of good recommendations through work. Stripe is an amazing place to build an impossibly large reading list.

I didn’t quite hit my goal of 20 books this year, but feel good about the material I did get through this year. If I had to pick, I think Men, Machines, and Modern Times, Democratizing Innovation, The Score Takes Care of Itself, and Sculpting in Time were my favorites of the year. I’ve left some notes on these books (and more!) in ascending order of completion below:

1. A History of Future Cities by Daniel Brook

I read this based off of this recommendation and found the juxtaposition of the histories of St. Petersburg, Shanghai, Mumbai and Dubai fascinating. Parallels with Silicon Valley, the rush of investment during boom times, speculators, generations of young men. Eventual bust and resurgence. Thematically, these cities were incubators for revolution, then shunned and curtailed when the revolutions actually occurred. Do the incumbents in Silicon Valley curtail the kinds of environments which fostered them?

2. Democratizing Innovation by Eric von Hippel

I spontaneously started reading this due to this Tweet. I wasn’t really sure what to expect, but engaged with the examination of user modifications to products and subsequent implications on manufacturing and product development processes. At Stripe our business is built on top of users who adopt a toolkit (our API and SDKs) to product a billing solution customized to their needs. The book examines the successes businesses have in identifying lead users who innovate, and rolling those innovations back into the main product to make it better for the main body of customers. A personal example: When developing our metered billing offering, many early insights came from seeing how our customers would create recurring $0 subscriptions every month, and add individual line items once the billing period elapsed. Examining these integrations helped inform the design of the feature to make sure we were satisfying use cases we observed.

3. Financial Intelligence, Revised Edition: A Manager’s Guide to Knowing What the Numbers Really Mean by Karen Berman, Joe Knight, and John Case

As a member of Stripe’s Billing team, I’ve relied on accountants for help understanding the problems our customers experience every day. I’ve started trying to educate myself more on this subject, and while Financial Intelligence isn’t exactly aligned with the products we develop, it served as a really accessible introduction to financial reporting (e.g. balance sheets and income statements) and a great way to learn more about revenue recognition. I really liked this book for the clear examples, conversational style, and interesting anecdotes. I’ve already recommended it to others on my team who expressed interest in learning about these subjects.

4. The Score Takes Care of Itself: My Philosophy of Leadership by Bill Walsh, Steve Jamison, and Craig Walsh

An observation about managing a team is that you can’t get to a high functioning team just by saying “we need to be the best team possible”. What I’ve found effective is focusing on fundamentals. I try to make sure that decisions are backed up with a rigorous methodology, best practices are established and followed, team members know how to unblock themselves and have the tools to do so.

I was going over this at some point in a meeting and my interlocutor said: “That reminds me of Bill Walsh. Have you read The Score Takes Care of Itself?“. Which I hadn’t then, but have now. Walsh’s philosophy is that if you focus a team on how to think and act and keep striving for perfection, then you don’t have to worry about winning games because the outcome is inevitable from doing everything perfectly. I’ve had my share of both successes and failures, but I can see that those things which have been outsized wins have not come from wanting the win really badly but from focusing on doing a good job and having a high standard of performance. For what it’s worth, I don’t think I got this sentiment directly from Bill Walsh but rather from hearing about Thomas Keller talking about cutting tape in his kitchen:

“Just the other day, Thomas was so proud to show me how they use painter’s tape in the kitchen,” Ruhlman says, visiting the Per Se kitchen one afternoon. Instead of tearing the tape from the roll to, say, label the plastic deli cups that hold the ingredients at each mise en place, every strip of tape at Per Se is cut with scissors, every edge perfectly straight. Immaculate. “Because it’s all one thing to Thomas. You can’t be lax in one area and perfect in another.

“It’s not about the sweeping vision,” Ruhlman adds. “It’s about the minute vision. There are no big decisions. A great restaurant is the result of a thousand little decisions. A place like this is just composed of details. It’s a pointillist picture. So every night after service, you’ll see Thomas down on his knees, scrubbing out the cupboards.”

You can’t be perfect in any one area if you’re willing to tolerate sloppiness anywhere, is how I take that.

5. Sculpting in Time by Andrei Tarkovsky, Kitty Hunter-Blair (Translator)

I watched Stalker as part of Cinema Club and it’s a movie which has stuck consistently with me for years. I was fascinated by Tarkovsky and decided to read this book of essays about filmmaking and his own path as a filmmaker.

It took me a long time (technically I started reading this in 2017) but I got a lot out of this book. I liked reflecting on how Tarkovsky considered the obligations of the artist along with how they relate to their audience and the ideal of a fundamental truth in art. As a creator of some things I can only appreciate how short I’ve fallen of his ideals and morals. While I doubt I could bring myself to the sacrifices he seems to call for in terms of keeping a pure vision in art and expression, I can still take things from his process and be better for having glimpsed it.

Cinema Club eventually spawned a dedicated Twitter account, and I Tweeted various excerpts and notes from the book which I found interesting.

6. From Seed to Skillet: A Guide to Growing, Tending, Harvesting, and Cooking Up Fresh, Healthy Food to Share with People You Love by Jimmy Williams, Susan Heeger

Steph and I have a small patch of gardenable space in our backyard and we started growing vegetables in earnest a couple of years ago. Steph’s gift to me for Christmas that year was this book, which I put off (I tend to read Kindle books quickly and physical books slowly due to how I structure my reading time). Steph read this book on gardening food-producing plants (with a focus on small urban gardens) before I did and started talking about worm composters, making our own fertilizer blends, rotating crops and so forth, which I laughed off. Of course, now that I’ve read the book I’m starting to obsess over these things too. Some of my favorite memories from childhood involve eating fresh berries, tomatoes, peppers, cucumbers pulled directly from various gardens. I’d love for our daughter Ada to have those experiences as well.

7. Tempo: Timing, Tactics and Strategy in Narrative-Driven Decision-Making by Venkatesh G. Rao

I’ve enjoyed following Venkatesh on Twitter and reading his Breaking Smart newsletter. He’s a master model maker and labeler of concepts and can seemingly generate sensible 2x2 models for any topic. I loved reading his models for concepts he calls Global Creolization and the Second World. This book provides some similar tools for developing decisions, but around the concept of tempo and rhythm for decision making. I’ll be honest that I didn’t get a ton of actionable items out of this, but with the caveat that I didn’t spend the appropriate amount of focus to work through his models and think through the questions he poses as exercises at the end of each section. This book was in a sense Theoretical Vgr, whereas I think I prefer Applied Vgr instead.

8. Procedural Generation in Game Design by Tanya X. Short, Tarn Adams

I was expecting more of a textbook covering a specific curriculum than the collection of essays this book turned out to be. I enjoyed it, though, as a quick read to get myself thinking about the potential applications of procedural generation for specific projects, rather than getting bogged down in approaches or exercises which may not be specifically applicable to anything I want to do.

9. The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change by Camille Fournier

This book was published last year but came up several times in a short period, from a former manager I really respect, to a company-wide Slack thread: “obligatory plug: The Manager’s Path is the best software engineering management book of all time i mean basically everything Camille writes is worth reading but the book is :1000: even if you have no intention of people-managing ever” and even from one of my direct reports during a 1:1. Of the various references I’ve found useful when learning about managing teams, this book does the clearest job of articulating the stages of a career progression, from software engineer, to tech lead, to line manager, to manager-of-managers, to engineering director and even senior executive staff. It’s the kind of book anyone in software engineering should read - a grounding primer on the expectations, illusions, and reality of each stage, and a great answer when, as a manager, your reports question “what do you do all day?“.

10. Games People Play by Eric Berne

Stripe offers an intensive 12-week leadership course for both managers and non-managers in leadership roles. I was fortunate to be able to attend the course this year, but it certainly didn’t help shrink the ever-growing list of recommended books I’ve been building since joining the company. I decided to read Games People Play not so much because of a strong endorsement (I think it was merely referenced in a presentation somewhere) and found it to be pretty dated. That being said, the “games” do seem to illuminate certain behaviors I’ve observed in both myself and others, and the Kindle version even ends with Kurt Vonnegut’s review: “Most people read the games first, I suspect, skipping the body of theory Dr. Berne carefully builds before them. Without doubt, it is the games that sell the book, for they have the queer ‘There’s-Aunt-Louise!’ charm of Abner Dean cartoons. But then one discovers all the solidly nourishing stuff up front and the book doubles in value.” Which seems about right.

11. Women Don’t Ask: Negotiation and the Gender Divide by Linda Babcock and Sara Laschever

I kept working down Star’s list from Democratizing Innovation. The audience for this book is certainly intended to be women, but a lot of the points were good reminders of the importance of spreading opportunity equally on my team, rather than waiting for individuals to ask directly. It also covers several biases (e.g stereotype threat, tokenism) which are critical to keep in mind as I think about opportunity on the team.

I even find the reminder to try and engage in more negotiation in life useful for myself, as I think I have the tendency to acquiesce to what I imagine the other side wants before fully expressing what I want. I’d heard of a negotiation course where they gave homework assignments to the class to “get someone to say no to you” to help get past this - the implication being that we rarely push on requests far enough for someone to definitively decline. Around the time I was reading this book I came across this great Tweet about goaling on rejection. Saying “I should have X failed negotiations next year” seems like a way to ultimately have more successful negotiations too, while mitigating the sting or crushing feeling of failed attempts from lots of at-bats.

12. Oh Crap! Potty Training: Everything Modern Parents Need to Know to Do It Once and Do It Right by Jamie Glowacki

Every parent needs to go through potty training at some point and for us it was Labor Day weekend 2018. This book came well recommended and I enjoyed the irreverent yet prescriptive tone. While 288 pages seems like a lot, the actual process fits into the first couple chapters, with several supplemental chapters to refer to when things go awry.

I appreciated having the guide to go through a surprisingly stressful time, but our own experience deviated a bit from the stuff covered in the book. I think we got to a point where we were putting too much pressure on things to go as described (which in itself is a failure mode described in the book) and things eventually went smoother once we were more willing to just let things happen (which is a troubleshooting technique covered in the book). I’d recommend it, but also caution that it’s not possible to rush, the technique described does not hold up to shortcuts and you should take the guidance on being mentally prepared in the first few chapters seriously.

13. Six Four by Hideo Yokoyama, Jonathan Lloyd-Davies (Translator)

Sometimes I’ll jump on a book based off of a strong recommendation, like this one which I randomly saw in my Twitter feed. I wasn’t sure what to expect, but a set of kidnapping mysteries told from the point of view of a Japanese police media relations officer was not it! There’s a lot of cultural context around status and relationship to the media which I felt like I was missing out on, but the whole story is pretty intricate, moves along well, and wraps up in an interesting and satisfying way. I’d say that you probably should be into procedurals or mystery novels, but this was an entertaining break from a bunch of nonfiction.

14. The Gray Rhino: How to Recognize and Act on the Obvious Dangers We Ignore by Michele Wucker

This book came up because I was in a job interview where the candidate had looked up the interview panel beforehand, read my Black Swan post, and recommended this as related reading! The concept of Gray Rhino is a high impact event which is foreseeable, and the book examines why systems seem to ignore or be unprepared for such occurrences. Michele Wucker posits that many people regard the US financial collapse of 2007-2008 as a Black Swan event, but it was in reality a Gray Rhino:

The financial crisis that spun out of control in 2007–08 was a Black Swan for some, but plenty of people weren’t surprised: the crisis in the making was a crash of Gray Rhinos converging. There were many warning signals that the financial bubble that grew between 2001 and 2007 was well on its way to bursting... The International Monetary Fund and the Bank for International Settlements issued repeated warnings in the years leading up to the crisis. In 2004, an FBI report warned of widespread mortgage fraud. By 2008, foreclosures were at record levels. Christine Lagarde, then the French finance minister, warned at the 2008 G7 summit that a financial tsunami was on the way. William Poole, the former president of the Federal Reserve Bank of St. Louis, and Richard Baker, Representative of Louisiana, predicted Fannie Mae and Freddie Mac’s problems... Goldman Sachs, as we now know, bet against mortgages through derivatives contracts it bought from AIG. It even took out insurance against the collapse of AIG, because it saw that coming, too. The lawsuits that followed the financial crisis showed in excruciating detail how many firms knew that a collapse was on the way and bet against the securities they were selling to their own clients.

This jibes with how friends in finance talked about their work pre-crash. I still remember getting a description of credit ratings on tranches along the lines of “this is all made up”.

The book itself reads like a fleshed out analyst’s report and serves as a starting point for a lot of other reading, including Nassim Nicholas Taleb’s own works. But as an overview of an interesting framework and a reminder about how easy it is to ignore obvious crises in the making as someone in a management / strategic position, I appreciated the read.

15. The Show That Never Ends: The Rise and Fall of Prog Rock by David Weigel

After the 2016 election, I started reading a lot of the Washington Post. I noticed that David Weigel seemed to write a lot of articles I liked, and that his bio mentioned a book about the history of Prog Rock. This seemed curious, so it made the list for 2018. As someone who likes Pink Floyd and always thought he would be totally into the genre, I have to say this book taught me a lot more about Prog Rock than I now realize I ever wanted or needed to know. The upside, is that I now get all of the references in this Venture Bros clip.

16. Scaling Teams: Strategies for Building Successful Teams and Organizations by Alexander Grosse, David Loftesness

I had the privilege of working at Twitter at the same time as David, and I think a lot of the references he draws upon from his time there feel very personal to me. I think the insights drawn in this book generally ring true and it’s a good, concise summary of many of the themes I’ve synthesized in my own development as an engineering manager at a Silicon Valley tech company. I didn’t always agree with the conclusions drawn from examples in the book (we have pretty different views on Twitter’s Hackathons for example) but I could still see myself recommending this book in the future.

17. Stubborn Attachments: A Vision for a Society of Free, Prosperous, and Responsible Individuals by Tyler Cowen

I picked this up because my company Stripe published it. While having heard people speak admirably about Tyler Cowen, I’d never actually read a book of his before, and I have to say that I was a bit surprised by how much philosophy this (relatively short) one contained. I appreciated how accessible he made his subjects through some direct thought experiments but he also happily gets into the uncomfortable territory of GDP growth is the best thing we can do for others (hence the title). Ultimately he makes a case that we as a society should think in longer terms and “be more concerned with the fragility of our civilization” which I can get on board with even if I tend to dislike the way others have taken messages like “productivity growth is better than welfare” and run these themes into terrible ends.

18. The Steel Kiss by Jeffery Deaver

The Steel Kiss originally made it onto my reading list due to a timely Hideo Kojima recommendation. I purchased it as a pulpy airplane book and discovered too late that it’s the twelfth installment in a mystery series which I have not read. However, I did go see the 1999 film adaptation of the first book The Bone Collector. I’ve also enjoyed movies and TV I’ve started watching halfway through, so why not books? Luckily, this is not a complicated book. In fact, it is a book which introduces characters in this manner:

She skidded the ’60s muscle car to a stop in a bus zone, tossed the NYPD official-business placard onto the dash and eased out of the car, minding the suicidal bicyclist who came within inches of collision. He glanced back, not in recrimination, but, she supposed, to get a better look at the tall, redheaded former fashion model, focus in her eyes and a weapon on her black-jeaned hip. Onto the sidewalk, following a killer.

If you can get past that, the book moves pretty quickly and has some twists I wasn’t expecting. It’s a really big contrast to Six Four, and I love the totally different styles of presenting stories of police officers tracking down serial killers. This one certainly gets points for going incredibly over the top. The book opens with a murder via escalator, which is honestly pretty inventive!

19. Men, Machines, and Modern Times by Elting E. Morison, Rosalind Williams, Leo Marx

Patrick Tweeted a quote from this book which I found compelling (much of the success I see at work is simply from making things explicit) so I started reading this and quickly found myself highlighting large swaths of the book on my Kindle. Like the gendered title indicates, it’s a bit dated, but this 1966 book is a fascinating account of how the American military and various American industries reacted to disruptive innovations in the late 1800s, plus some forward-looking writing from the point of view of the 1960s. I thoroughly enjoyed the history lessons, but was fascinated by how familiar some warnings about the adoption of computers seemed. Here’s a notable passage, especially in light of contemporary debates about AI and bias:

In dealing with the computer, with its incisive capacity to reach clear decisions from the data presented, we will find ourselves in grave difficulties, I think, if we persist in such sloppy definitions of the problems we wish to solve. We will have, in the near future, to ask ourselves if we can assess even quantifiable data without distortion; we will have to painfully consider whether we are ready to lift out our raw affections for observation and analysis, whether we are honest enough and brave enough to make the necessary separations between the indispensable and the irrelevant feeling.

The book has a message about the dangers of being too fixed in our own ways. I was struck by this bit about engineering preferences:

Then there is the apprehension about the computer as a fascinating gadget. It is obvious that there is always danger from the gadget-happy, whether the gadget is a machine, an idea, or a procedure. Amasa Stone, for instance, a very able man, killed a trainload of people because, against advice, he built a bridge at Ashtabula from a truss design for which he had an ancient attachment.

The entire book is beautifully written, and was one of my favorites of the year. I’ll leave with this meditation on complex systems:

Sigmund Freud had a theory that art is merely a neurotic compromise, an enormous effort by men to give reality in the imagined abstract to desires they could not fulfill in action. It is possible that our affectionate attachment to particular schemes of value are equally symptoms of our incapacity to run an environment in a reasonable way. For instance, in the thirteenth century a man petitioned Almighty God only perhaps because he thought he could control nature in no other way. Or a man in the nineteenth century made hard work, thrift, giving to the poor, and the sacredness of individual enterprise into a scheme of value because they were the only devices that enabled him to deal with an uncertain economy he could not run or understand by his reason alone.