Generally speaking, when people use the word fun, it's like a placeholder. You know, "How was your evening?" "Oh it was fun."

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.

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.

I think this dichotomy or opposition between work and play, between leisure and serious stuff, is definitely a bad way of thinking about the useful insights that play provides.

Normally we think of play as the opposite of work. Work is the thing you have to do, and then there's play, the thing you choose to do.

If you stop someone who's talking about something being fun, and say "Well what do you mean?" it's almost impossible to answer.

Actually a lot of the supposedly serious and meaningful and worthwhile content on the podcast or on the television is no more or less meaningful than the clothes in the laundry basket or the dishes in the sink. It's more a matter of the attention you're willing to bring to them, where you're willing to allow meaning and pleasure and the light to escape.