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As soon as I was old enough to learn, my father taught me to play chess. He was not a chess player himself, but he knew the basic rules of the game, and he thought it was something I ought to know how to do.

Chess was way more interesting than checkers. I loved how each piece had its own way of navigating the board, and how the game’s idiosyncratic choreography led to unexpected situations that I had to improvise my way out of. After playing a few introductory games with my father, I began to play with my friend Carl, who lived across the street.

Carl was as new to chess as I was, so our games were played just for their entertainment value, mostly as a way to pass the time on rainy days. In a sense, I viewed chess the way I’d later view a game of Twister: The outcome didn’t matter so much as what sorts of interactions happened on the board.

Then, one day, everything changed. Shortly after our game began, Carl’s rook advanced inexorably toward me, and when it got far enough into my territory, it began to knock off my pieces, one by one. The game ended quickly, before I’d had much of a chance to do anything. The next game went the same way. Obviously, Carl had been studying.

What I discovered that day was that my father hadn’t really taught me chess. He’d taught me the rules of chess, but he’d left out the main part of the game, which was analyzing your opponent’s weaknesses, predicting how each move would play out down the line, and working out a strategy to limit your opponent’s available defenses against your attacks. In other words, it was about ruthlessly driving your opponent to defeat.

This is supposed to be the part of the story where I vow to learn all I can about chess strategy so I can exact my revenge on Carl, and go on to vanquish much better players. But in truth, that idea never occurred to me. I’d never seen the point of competitiveness. Sure, losing felt bad, but winning meant making my opponent feel bad, and where was the pleasure in that? I’d always thought that the idea of one person winning and one person losing was just to make sure that games had a way to end. If playing chess meant investing time, work, and emotional energy into defeating the other person, I didn’t see the point. It made much more sense just to quit playing chess.

While my father had been the one who introduced me to chess, it was my mother who taught me to play Scrabble. As with my father and chess, my mother was not a Scrabble player — mah jongg with “the ladies” was her game of choice — but she thought that learning Scrabble would encourage my interest in language, which was something that she shared. The Scrabble board was a place where I could show off the breadth of my vocabulary and engage in creative problem-solving, so playing the game came pretty naturally to me. My mother usually won, but that seemed only fair, since she was the one did the Sunday New York Times crossword puzzle every week. Part of the fun was watching how elegantly she played the game.

It was not until years later that I discovered that I had been as wrong about Scrabble as about chess. For real players, Scrabble was not about vocabulary at all. Playing it well required memorizing lists of words, but it wasn’t necessary to know what the words meant or how to use them in a sentence. For purposes of the game, they were merely sequences of letters, as arbitrary as the winning tile combinations on my mother’s mah jongg card.

Worse, Scrabble was as much about playing aggressively as chess had been. It wasn’t enough to make good use of the letters you’d drawn; you were supposed to keep track of which letters your opponents were likely to have, and prevent them from laying down the ones with higher point values. In fact, you were supposed, as much as possible, to prevent them from putting down any letters at all. Whenever I dared to play Scrabble as an adult, I was berated by my opponents for making it too easy for them. “Look!” they would say disparagingly. “You just opened up this whole section of the board for me!”

I didn’t get it. I thought I was doing a good thing. I always came up with my best Scrabble words when I had numerous options as to where to put my letters, so why wouldn’t I want to give other players the same opportunity? To do otherwise just felt mean-spirited.

Now that I think about it, I guess I’m just uncomfortable with the whole idea of strategy. Strategy has its places — for example, I try to load the dishwasher strategically, so that I can keep adding dishes throughout the day without having to rearrange anything — but in interpersonal affairs, it feels cynical. Strategizing means trying to outsmart other people, to take advantage of their blind spots, rather than aiming to be generous toward them. It’s certainly not an attractive part of human nature.

I understand that in the real world — particularly in business and politics — it’s often necessary to act strategically. People whose interests are different from yours are going to try to outmaneuver you, and they’ll do whatever they can to find an edge. You may need to do the same in your own defense. Games of chess, from what I understand, were long considered a training ground for military strategists, allowing them to cultivate skills that would aid them on the battlefield. Napoleon, for example, was known to be an avid chess player. But while I understand the necessity of learning those skills, I can’t find a way to experience them as a source of pleasure — especially among friends. We may live in a world of winners and losers, but recreate that world in microcosm on a game board? I don’t want to spend my leisure time plotting against people; I want to find ways to share with them.

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Since You Asked

Sometime in the 1980s, before the internet was in common use, a friend came to me with an odd request. “I’m doing a ten-mile walk for charity,” she said. (I don’t remember what the charity was.) “And I’d like you to sponsor me.”

“Sponsor you? I don’t get it,” I said. “Where are you walking to?

“We’re not walking to anywhere,” she said. “It’s just to raise money. Like, if you pledge two dollars per mile, and I walk the whole ten miles, then you donate twenty dollars.”

“And if you only walk five miles, then I only donate ten dollars?”

“That’s right, she said. “But I’m planning to walk the whole ten miles.”

This made no sense. “If you’re asking me to donate money to this charity, that’s fine. But what does your walking have to do with it? Why does the worthiness of the charity to receive my money depend on how far you walk?”

“That’s just how it works,” she said.

“But I could just donate twenty dollars, because you asked me to,” I said, “and then you wouldn’t have to walk at all.”

“Twenty dollars is fine,” she said. “I’ll put you down for two dollars a mile.”

So she got what she wanted, but I felt like no actual communication had taken place. I still saw no inherent connection between the money and the walking.

I wish I had a more satisfying ending to this story, but I don’t. Nowadays, I see plenty of requests from people who are walking (or running, or biking, or swimming) for charity. And the weird thing is that nobody seems to see anything strange about it! Everyone just accepts that a person’s engaging in an unproductive physical activity is a rational reason to donate money. When I donate, it’s because the charity is worthwhile and a good friend asked me to; I don’t care what my friend does for exercise.

But I’ll tell you what I won’t do — I won’t vote for someone just because they ask me to. The situation is usually like this: A friend will email me (usually as one of many “undisclosed recipients”) with a message like, “I entered Floofy in the World’s Cutest Dog contest, and if he gets the most votes, I win a lifetime supply of pet food. So please vote for Floofy as the cutest dog, and tell your friends to vote for him too!”

Originally, I used to take these requests seriously. I would have to reply, “I’m sorry, but I don’t have time to look at the pictures of all of the dogs, so I have no way to confirm that Floofy is really the cutest.” And they would respond, “What do you mean? I’m just asking you to vote for him. I’m your friend — don’t you want me to win the pet food?”

The thing is, if everybody votes for a particular candidate because someone asked them to, then the adorable dog photos that everyone uploaded serve no purpose at all. The winner of the contest is not going to be the cutest dog; it’s going to be the dog whose owner has the most friends. That makes the whole thing a lie. Why not just call it a popularity contest? I just ignore those kinds of requests.

Unfortunately, the contest entrant’s way of thinking also pops up in more significant situations. When I was a faculty member at Chabot College, in my roles both as a department head and a committee chair, I was often in the position of having to request things from the administration. Naturally, the equipment or staffing that I was asking for cost money, and there were other people whose roles required them to compete for the same pot of money. I would fill out the appropriate forms, in which I would make a compelling argument for why my request was necessary, but I almost never got what I was asking for.

“Of course not!” my colleagues would say. “You can’t just go through official channels. You have to advocate! You have to get in their face! You have to convince them that what you need is more important that what other people need!”

But there’s no way I could do that, because in truth, I had no idea whether my needs were more important than others’. The only people who had the information necessary to prioritize the various requests were the administrators to whom the requests were made. That’s why we had to fill out forms — so that the administrators could do their job, which was to analyze the competing claims and make justifiable decisions. If their conclusion was that other departments’ needs were more urgent than mine, I had to respect that determination.

I don’t want to live in a world where the resources go to the person who yells the loudest, or the dog food goes to the person with the most connections. For that reason, I have to trust that other people don’t, either.

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