With sports and games, you have fun despite working very hard, even despite failing repeatedly. Even the fun of a night out, you have to get somewhere and do all the conversational, social work of being out. There's effort involved. But then when you're finished, you can conclude, "Actually there was something gratifying about the hardship that I just encountered." That discovery of novelty is where the molten core of fun is.

We're stuck in these situations with other people and our stuff and our jobs, and thinking that we can extract ourselves from those seems doomed to me. Instead, how can we live within those systems of constraints? We don't have to enjoy them, exactly, but at least acknowledge that those boundaries are real and that they structure our response to the world. And then once you do that, you allow yourself to say "I did my best given the circumstances."

The whole idea of play is in finding, acknowledging, and then working with the natural constraints and limitations that you find in the world.

Forcing your spouse to stop doing that bad habit that drives you crazy, or making your kid be better at math or at art or at swimming, or making your parents or your in-laws not be annoying in the way that they're annoying, these are sometimes doomed goals.

You can experience play at work, not because you're messing around or wasting time or something, but because you're looking really deeply and seriously at things and asking what is possible, what can be done with them, what new ideas might emerge?

Even when we tell kids to go play, what do the kids do? They come up with a set of constraints and structures. "Oh, we're gonna build a fort out of clothes, and now that we're in the fort we're going to pretend that we're prisoners," or whatever.

The problem with fun is we really don't know what fun means at all.