Playing to Play: On the contradiction of playing to win

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You should have taken that bishop! Why didn’t you take that bishop? You had the game won!


A dominant sound in professional, personal and spiritual development is to worships at the altar of BIG.

Play Big.

Play Bigger.

Play a Big Game.

Play a Bigger Game.

Play a Big Game You Can Dominate.

Play a Bigger Game You Are Destined to Win.

And it goes on quite hyperbolically. There is a point to this sort of expansive talk because we fall into the habit of seeing ourselves as quite limited. We are limited in some ways and in others we are not.


When P first sat down at my table he just wanted to chat. But eventually he saw the chessboard there and wanted to play. The pieces slid out of their cardboard tube and were arranged on the board. Crowds bustled and strolled on that bright and windy day.

So we started to play. I know the rules of chess and appreciate the elegance of the game but I am an amateur of the first degree. I can rarely see more than a two or three moves ahead…if that and hardly show any skill for setting up grand traps or 11-dimensional strategies. But I enjoy the game and seeing the way the lines of force show up on the board. I like that a feminine piece is the most powerful on a board with 28 squares around the perimeter – each symbolizing a day in the phase of the moon.

Each game is a cosmic act.

P was an amateur as well, though a better player than I.

We chatted broadly and the whole experience was just lovely.

And then I inadvertently set a trap. All my pawns on the right side were in a big diagonal line and had trapped one of his bishops.

I saw that if I took his bishop that the game would be over in a few moves. The entire right side of the board would have been wide open and his King and Queen were trapped. The game was as good as over.


Playing a game so that we can win it is an action filled with contradictions.

Because we play to win we feel the weight and the obligation to try to win. In so doing we take away or abrogate the freedom to simply play. Those who must play can’t actually play freely at all. The constant attention to progress towards winning makes every move critical…it must be made in order to secure the title of winner!

So in order to  play a game we must engage in some level of seriousness which is counter to the full spirit of play. When and if you “win” a game – chess or otherwise, you now have a title of “Winner” and this is a title that looks backwards in time. It points towards accomplishments you secured in the past. If you win enough you might be considered a “Master Player” who is so good at playing the game that this Master Player can’t even be approached on the field of play because they are so good. So in playing to win we drive towards a place and a space where play is no longer possible.

Winning a game (or an argument or a title or some kind of status) can be quite contradictory. Playing for the sake of playing can be quite paradoxical.


So at that moment I saw that I had the game won. But I was enjoying the process of playing and the process of chatting with P. Knowing that I had essentially won was enough but to take it was a choke point. To win would be to end it at that moment. So I made an intentionally weak move on the left side of the board that allowed us to exchange Queens but not before P with anger and exasperation said

You should have taken that bishop! Why didn’t you take that bishop? You had the game won!

It was more fun for me to continue to play than to claim the title of winner. Not only was the act surprising to P but it freed me to be surprised for the rest of the game as well.


In the cult or culture of winning and bigness we inadvertently cultivate a seriousness that kills our capacity to either be surprised or to be delighted by surprise. When we are playing big or playing to win or playing a game that we can dominate…surprises tend to be unwelcome.

Only in releasing our need to win and claim a title can we free ourselves from the exercise of power over others or situations and be free to embody the strength in ourselves. There true creativity arises.

If the point of our play is to be so good at playing that no more play is possible or necessary then our play has ceased. Why are we doing this?  For example…

“I want to be so successful that I’m a billionaire and I don’t need to do anything any more”

The cosmic act of chess or the cosmic act of our professional or personal activities and development can align with the way the cosmos acts itself…it does not seek to win or to lose. It simply seeks new ways to express itself. And if barriers for that come up…the cosmos uses those impediments as part of its approach to express itself.

Have you seen how playing to win and playing big impedes with actually playing? I’d love to hear your experiences on this.


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Have you read Finite and Infinite games by James P. Carse?

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