Favorite Reads of 2020

In 2020, I set out to read 40 books. Somewhere in the middle, a lot of goals and plans went upside-down. Amid the chaos, I found more time to read. And so I ended up reading 50 books over the course of the hellish year. Some were short, some were long. I read some fiction and some non-fiction. I read a few things to help me grow as an engineering manager, I read a few things for fun, and a few of the things I read fit both categories. Here are my top twelve reads of 2020 – in the order in which I read them – with a few pullquotes here and there.

Ten Reads of 2020

Thinking in Bets, Annie Duke. A remarkably easy read, Thinking in Bets comprises champion poker player [Annie Duke’s leadership strategy. We know that leadership by consensus is inappropriate. And we also know that we have to make decisions with limited information. Duke wraps a bow around all of this and encourages leaders to make decisions as though they were placing bets. She equates decision-making in poker to decision-making in business and management, You don’t need to be certain about everything. You need to understand your uncertainty and make your decisions accordingly. This one fundamentally changed the way I approach decision-making.

One of the things poker teaches is that we have to take satisfaction in assessing the probabilities of different outcomes given the decisions under consideration and in executing the bet we think is best. With the constant stream of decisions and outcomes under uncertain conditions, you get used to losing a lot. To some degree, we’re all outcome junkies, but the more we wean ourselves from that addiction, the happier we’ll be.

Boom Town, Sam Anderson. In a former world in which we ate lunch with coworkers in person, a colleague mentioned they were reading a book that combined the NBA with U.S. history. I was hooked. Sam Anderson is a New York Times columnist who spent a year in Oklahoma City. The year he spent coincided with the Oklahoma Thunder’s first year after trading future superstar James Harden. Anderson chronicles the founding of Oklahoma City, its 20th century history and identity as forgotten in the national culture, and the stake in the cultural zeitgeist that was them landing the NBA franchise. The book weaves these stories with essays on The Flaming Lips, the city’s urban redevelopment in the second half of the 20th century, and, of course, the bombing in 1995.

The Making of a Manager, Julie Zhuo. Julie Zhou was an early team member on Facebook’s design team, and she got to help grow the team out first as an IC, then on the people path up through VP. The lessons she lays out are targeted for tech companies, but generic enough to span beyond the design function. In a sharp ten chapters, Zhou expertly describes the role of EMs and some of the trappings and travails of the job. For a long time, High Output Management was my go-to book recommendation for new engineering managers, but I always felt awkward asking new EMs to translate the lessons across decades. I can now recommend The Making of a Manager, and I stress no more.

This is the crux of management: It is the belief that a team of people can achieve more than a single person going it alone. It is the realization that you don’t have to do everything yourself, be the best at everything yourself, or even know how to do everything yourself. Your job, as a manager, is to get better outcomes from a group of people working together.

Atomic Habits, James Clear. James Clear lives up to his name with a dense and easy read on building good habits. In his advice, Clear toes the line between ambition and apathy. I found I had applied his lessons in building up some of my good habits, and I had ignored them in places where I have yet to build them up. The book spends a good amount of time covering how to build good habits, but it also brilliantly spends some chapters on breaking bad ones. Clear is upfront with you: you won’t make it on willpower alone. Amen.

Fleishman Is in Trouble, Taffy Brodesser-Akner. Fleishman Is in Trouble was my favorite novel read of last year. Fleishman is a newly single father watching his two kids in Manhattan when his ex-wife fails to show up for her pick up. The narrative is the star as Brodesser-Akner embodies the 40-something Fleishman who is at times hopeful, reticent, regretful, and pliant. The further the author takes you into Fleishman’s head, the more you start to wonder who you have been rooting for. And then, Brodesser-Akner sweeps through the world she’s created in a Flynnesque second act.

Time was going to march on anyway. You were not ever going to be young again. You were only at risk for not remembering that this was as good as it would get, in every single moment—that you are right now as young as you’ll ever be again. And now. And now. And now and now and now.

The Victory Machine, Ethan Sherwood Strauss. I picked this up as a vacation book. Sports were paused, and I needed a fix. The Victory Machine tells the story of the how the Warriors super team rocketed to success and ultimately how it fell back to earth. Each chapter focuses on a player or coach at a particular juncture in the journey. It was particularly insightful to hear how Steve Kerr approached joining the Warriors in the first place and the care and strategy he put into starting the new job. I would recommend that chapter to any sports fan who wants something a little lighter than The First 90 Days.

The New Jim Crow, Michelle Alexander. A lot of my favorite reads of the past few years are a mix of fiction, non-fiction books that inspire me, and a smattering of management and leadership books. While I can say that this book inspired me and it does touch on leadership, I’d be remiss to not call this book the devastating read that it is. The book is ten years old, and it sadly could have been written right now. Alexander flashes a spotlight on the systems that operate in this country that were both designed to hold back people of color and to make the system itself virtually impenetrable. Each chapter focuses on a different microsystem (e.g., legislation, police enforcement, prisons), and each supports her central thesis that we are currently living in a new Jim Crow Era. I recommend this book to anyone who lives in the United States.

One theorist, Iris Marion Young, relying on a famous “birdcage” metaphor, explains it this way: if one thinks about racism by examining only one wire of the cage, or one form of disadvantage, it is difficult to understand how and why the bird is trapped. Only a large number of wires arranged in a specific way, and connected to one another, serve to enclose the bird and to ensure that it cannot escape.

Neuromancer, William Gibson. Neuromancer did that wonderful thing where I stop multiple teams in reading it just to check when the book came out. The book is the genesis of the entire cyberpunk subgenre, and it’s clear throughout that many modern, more popular pieces of science fiction owe themselves to this novel (see: The Matrix and Ready Player One). The futuristic novel takes place in a world where people can enter and engage within a lifelike virtual reality. The main character is a former infamous hacker who, after a failed job, had his body altered so that he could no longer enter the alternate world. He’s a disheveled shell of himself until a new player offers him a chance to reverse the procedure for one last job. Gibson masterfully puts you directly in the world offering just enough context clues to keep you hooked without losing your motivation. Gibson’s debut novel was published in 1984.

The Sound and the Fury, William Faulkner. I went to school down South, and while I was there, I became friends with a particular party animal. He was the kind of guy that would make sure the party had enough beer, and that everyone was having a good time. At some point on many nights, he would tell everyone that would listen that his favorite book was The Sound and the Fury. I remember this making sense to me at the time. It’s by Faulkner, and all I knew about Faulkner at the time is that he was revered in Mississippi. I always promised my friend I would read it, and for some reason, I told myself I would read it in the Fall. Brilliant, challenging, and ultimately, devastating, Faulkner tells the story of a wealthy family damned. Over the course of four parts, The Sound and The Fury focuses on four different members of the Compson family. The families troubles start away from these four characters and even the second-order consequences of those troubles are driven by supporting characters. The reader is left to put together these characters from the four vantage points given, and the effect is that of four family members whose lives are happening to them, rather than them exhibiting much, if any, agency. It’s a classic for a reason.

Because no battle is ever won he said. They are not even fought. The field only reveals to man his own folly and despair, and victory is an illusion of philosophers and fools.

Total Recall, Arnold Schwarzenegger. When I became an engineering manager, I stumbled across a podcast on leadership and startups called Seeking Wisfom. The show was hosted by the CEO and Head of Marketing of Drift, and the two focused on how they built their business and how they grew their people. They talked a lot about books, and there was one book I was surprised to hear them continually reference. You have an idea in your mind of who Schwarzenegger is. You might have two or three ideas. This man’s life is so full you have barely scratched the surface of his accomplishments and his philosophy. And it’s heart, the 600+ page memoir is a book on leadership and ambition. Schwarzenegger started as a kid in a small town in Austria before he set his sights on bodybuilding, then acting, then business, then politics. His philosophy is summarized in ten rules at the end, including: Forget Plan B, Reps, Reps, Reps, and Stay Hungry. And, unintentionally, the ending reads as the Greek tragedy that a massive part of his life became.

The First 90 Days, Michael D. Watkins. This book was recommended to me at least three times as I joined a new org this past Fall. TF9D focuses on strategies and tactics to employ when starting a new job. It suffers from generics in that it’s meant to apply broadly across industries, but if you put in the effort of translating, you can take away a playbook that can help you succeed across a number of onboarding scenarios. Given that the book spends half its time on starting at a new company and half on starting a new role within your current company, you could probably read this book in half the time.

Your goal in every transition is to get as rapidly as possible to the break-even point. This is the point at which you have contributed as much value to your new organization as you have consumed from it.

Love Is a Mix Tape, Rob Sheffield. This book came out around the time of Nick and Norah’s Infinite Playlist. It felt like the zeitgeist was going through a music as physical object resurgence. I never quite got around to this one, so when a friend put together a list of ten potential books for us to club together, I called this one out. Of course, Love is not a piece of fiction. It is a long-time Rolling Stone writer and editor’s ode to the music that shaped his life. Most importantly, it’s a story of the people in Sheffield’s life that were stitched together with the ribbons of so many cassette tapes. I finished this book holding music and loved ones more dearly. Quite the accomplishment from the music critic.

Dan Ubilla is obsessed with the craft of engineering management

He writes every two weeks. Sign up below for early access to his blog posts.

    We won't send you spam. Unsubscribe at any time.