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.

You don't want to be told, "Hey, do whatever you want." That's what we think of when we think of play. It's the thing where you get to do whatever you come up with in your own mind, all bets are off, there's no boundaries.

This willingness to be frank and plain about the way that the world is, is a good first step. But that doesn't mean that you get what you want.

When we use this word fun, it sort of bangs up the ordinary and the extraordinary altogether.

We think we want enjoyment, and that enjoyment is incompatible with work, and somehow we have to import the pleasure into these miserable experiences. That takes for granted that there's not fun or play to be found in the work itself.

We know exactly where the path to despair and insanity lies. It's in that sense that life is meaningless, there's nothing about today that's worth doing because it's just like yesterday and it's going to be just like tomorrow.

The more you're drowning in familiarity, the better the fun is. It requires less novelty to produce even more gratification. And it's something that didn't come from you. It was about the other thing - the thing you were experiencing, or the people you were with, or the mechanism you were operating, or whatever it might be.