Careless Players

A response to reading Careless People by Sarah Wynn-Williams.

My reading list is fluid. Although I usually know what I intend to read next (planning is part of the joy), occasionally my local library gives me an early ”Skip the Line” short-term loan of an ebook that disrupts the list. This happened Friday afternoon when a copy of Sarah Wynn-Williams’ Careless People showed up. I wanted to read this controversial book about Facebook that Mark Zuckerberg was trying to suppress since the author is a former employee. I had no special desire to read disparaging things about Meta, but the so-called Streisand Effect made the attempt to ban this book more interesting to me. Nice job, Zucky.

Sarah Wynn-Williams tells a devastating tale of the amoral (and sometimes just weird) behavior on the part of Facebook‘s leadership from Zuck on down, including his longtime heat-shield, Sheryl Sandberg. I suggest you read it to see how Meta’s management is alleged to have callously ignored the health and well-being of their employees and, more importantly, the stability and safety of the world, in their relentless pursuit of power and money. It’s essential reading.

There’s plenty of material to address, but the vector that inspired me to put fingers to keys is how board games occasionally played a role and learning opportunity in the tale. Wynn-Williams is clearly a board game player and the few times she mentions playing with Mark Zuckerberg are notable. I assume he learned the board game Catan from Reid Hoffman, a former Meta board member, my CEO crush and an avid fan of the hobby. Reid has often referenced game play and its value in his work. Zucky, to hear Wynn-Williams tell it, hasn’t managed to grok much out of his time with ‘these games of ours.’

Early in the book, Wynn-Williams talks about playing Catan with Zucky and a couple of obsequious employees. If you don’t know Catan, it’s a modern board game that involves building out settlements, roads, and cities on an island, gathering resources, and buying development cards to get to 10 victory points and win the game.

Unlike most classic board games, it’s more competitive than confrontational, although there are some ways to get victory points via competition. Much of the game involves trading cards with others to get the resources you need to build. This is often necessary since you can’t rely on your resource production because they are doled out randomly each turn. You can also steal from others if you roll a 7 on two dice (i.e., the most common roll), where you move a Robber Baron pawn to block someone’s production and steal a resource card from them.

When Wynn-Williams sits down to play with Zucky and these other two subordinates, both of them seem to do everything they can to help their boss win the game. Whenever he wants to trade with them, they do it immediately, even if it makes little sense for them. Wynn-Williams suspects this is happening until, late in the game, one of the players puts the Robber Baron on the other player instead of Mark, who is close to winning. She is so overwhelmed by the fact that they are obviously playing to let him win that she can’t help but call it out. As you might expect, the other two players act like nothing of the sort is happening.

When she questions Mark about it, he seems oblivious to the meta-game they are playing. They don’t care about winning a silly board game if it will make their boss upset. When the author presses the point, Zuckerberg is literally confused by the idea that anybody would do anything different. She surmises that he’s been in a bubble where people treat him like this for so long that he can’t even detect that there’s an issue. Perhaps people are used to letting children win games when they are really young (something that I say should stop as soon as possible), but this is a man - at the time - in his thirties.

This component of the book particularly interested me because I’ve written a book about how playing board games can have an impact on how we work and live in the world. In this case, it’s clear that the real-world meta game (no pun intended) is having an outsized impact on their gameplay. The author, who is from New Zealand, clearly had a different perspective than the toadies also playing the game. They’re Americans who are just being practical, figuring it’s worth it to throw the game to their CEO if it might help their rise in the company. With someone so obsessively competitive, they likely figure it can only hurt them to beat him at some silly board game.

While it’s hard to argue with the actions of these players, it’s disappointing that they felt this way. I’ve been bringing board games to work for decades, usually playing with people who were technically subordinates, but I never expected them to do anything but play to their ability and compete. That said, I once publically defeated a senior leader at my company in a board game after a gaggle of his direct reports told me how good he was. The guy never liked me after that experience. His behavior made me assume he had a low self-esteem, and that bore out over time.

Later in the book, Wynn-Williams references board games again when she plays directly with Zuckerberg. This time, it’s a game of another modern classic, Ticket to Ride. They play it head-to-head this time and she cleans Zuckerberg‘s clock, which surprises him. Of course, it doesn’t surprise me. If you’re used to playing with people who enable you to win, how will you develop the skills to be successful? Naturally, he won’t learn the best strategies to win.

This is why I’m such a big advocate for games. The tabletop game is supposed to be a safe place where you can compete, experiment with strategies, and learn how to deal with too much to do and not enough time to do everything. The best modern board games give us this challenge. You need to think about the opportunity cost of each action. While it might help you do something great, what are you giving up? Plus, it gives you a little window in game theory since you need to react to how someone else is reacting to the game state. We get stronger from these challenges and these skills are transferrable to real-world work and education activities.

Yet, if no one challenges you in these games because - in the real world - they worry that their actions on the tabletop will affect their job or performance reviews, you all lose. You will never build the skills to succeed - and if you have those skills, you will see them atrophy. You don’t get stronger by having things handed to you.

Shortly after their Ticket to Ride game, Wynn-Williams gets another chance to play Catan with Zuckerberg. Wynn-Williams actually wins the game this time, but she’s surprised that she does. Looking at the board, she tells Zuckerberg that he could’ve already won if he had not let himself be so focused on trying to claim The Longest Road tile. Again, if you aren’t familiar with Catan, there are a variety of ways to gain victory points, including building settlements and cities, which usually form the primary component for getting victory points. You can also get points for picking up development cards, and two competitive tiles that only one person can get, the Longest Road and the Largest Army.

Both of those tiles provide victory points, but you can lose those points if you fall behind someone else’s road length or army size. The skilled Catan player only competes for these tiles after weighing their value against the more reliable sources like building out settlement and cities. If you happen to fish more Army cards from the Development Deck or need to build a lot of roads to expand, then go for it. But you don’t ignore a path to victory just to compete for them.

Well, you shouldn’t. Overly competitive players often chase these tiles because they cannot abide someone ‘beating them’ in this sub-game. But you don’t need either of these tiles to win. You just need 10 points, however you earn them. Wynn-Williams points this out to Zuckerberg, noting that if he wasn’t trying to win EVERYTHING, he could have just won the game.

Zuckerberg‘s inability to win in this situation feels like a metaphor for a problem we have with late-stage capitalism. Without firm progressive taxation in place, where the largest earners pay higher taxes to the government for the good of the country, high net-worth individuals stay focused on simply ‘winning,’ by finding tax loopholes, acquiring businesses to endlessly expand even when it makes little sense, and perhaps trying to be on the Forbes Billionaire list. Without the understanding that they are already winning in the game of the American Dream, they keep trying to dominate yet another market, expand into yet another category, and even work to suppress those who disagree with them. The concept of ‘enough’ has lost meaning for these folks.

In other parts of the book, the author alleges that Zuckerberg’s obsession with getting into China caused the company to act in a variety of morally repugnant ways. From callously ignoring the wellbeing of their employees, treating subordinates like serfs who should go to jail in the name of business growth, and even ignoring the rule of law, it’s shocking what she says they have done just to grow their already successful business into a troublesome, if huge, new market.

Zuckerberg’s blindness about being able to win the Catan game because of his focus on dominating everything shows why Meta has had so many questionable business dealings in the past. If you need a reminder, there was the Cambridge Analytica controversy, whistleblower Frances Haugen’s revelations about how Meta ignored research showing the devastating harm they were inflicting on young people, and myriad acts of disinterest on the world stage because of the company leadership’s lack of concern for how their platform was causing harm. Everything from harm to teenage girls to the genocide in Myanmar was simply viewed through the lens of how it helped Meta expand and grow their business. Over and over again, they’d claim that they’re going to do better, but the author’s book notes that there was never any intention of doing anything that wasn’t about the company’s bottom line.

Some may find it silly to suggest that if Mark Zuckerberg was better at a board game, maybe he would understand the world a little better. That’s fine, but I certainly believe it wouldn’t hurt. This is why I wrote my upcoming book, Optional Rules: Variants for Life I Learned from Board Games. I believe that board games are a proving ground that enables us to understand how to play by the rules and be successful in life in a closed environment. When you have rules in place that everyone agrees on, your creativity, grit, and integrity can guide you to victory. When we say that the rules simply don’t apply for people with a lot of money or power, the entire game is just a bad joke and not worth the time spent. Winning a game that matters will always be more satisfying and positive for everyone involved.

Bad Games Encourage Bad Behavior

This is also one reason I hate the quintessential US board game, Monopoly. Yes, I’m one of those snooty gamers who take issue with the unappealing mechanisms it's built on. Roll-and-move randomness is boring. The notable lack of decision-making, from just drawing cards that have an immediate impact on you to losing turns because of the whim of dice, just doesn’t appeal to most game connoisseurs like me.

But forget all that. The real reason I loathe Monopoly is the message it sends. Monopoly teaches you to be mean and ruthless in your pursuit of money. Being successful in Monopoly’s dark world means bankrupting everybody else so you can have all the money for yourself. The goal is to raise rents so high that people can’t pay them and that you can only win when everyone else loses everything they own. You knock your friends out of the game so they can sit on the sidelines with nothing to do, nowhere to live, and not a dollar to their name. They just watch you amass more wealth than you will ever need while they have zilch.

Yes, Monopoly is an abomination to me because of what it teaches young kids and families: That late-stage capitalism is the way to win. For all the apologists that talk about the nostalgia that they’ve experienced from those four-hour plays of this monstrosity that ended in a fist-fight, please get over it. I say it’s time to let it die as the poster-boy for board games in America.

Let’s instead encourage games like Catan, where you trade and you negotiate and you build your civilization out without tearing down the other civilizations on the board. This is a game where you might not be the big winner, but you can see how well you do in the context of that game. While you might not get to the magic 10 victory points you need to win, you can look at what you built and be proud of it - even if it’s only worth 5-7 points. Next time, you can do better because you learned about weighing the options that provide the most value instead of slavishly worshipping wealth at all costs.

Catan still has competition. The Largest Army and the Longest Road can be components of winning the game. But they aren’t the only way to win. The world deserves better board games that support values that help us realize there is more to life than amassing wealth. There are other ways to win. There are plenty of them out there that could help both kids and adults realize that dominating all the money and power isn’t the only way to win.

I hope one day Zuckerberg will actually play more board games against people who have the moral fortitude to challenge him rather than simply enabling him to be less than he could be. Enabling billionaires to be the least version of themselves has consequences, as we unfortunately see every day now.

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