I find it helpful to remind myself on occasion that this interest in Zhuangzi and the rest is a kind of game. As I see it, the more like a game I see it, the more playfully aware I am that it is a game, the more it works its magic. Playing this game playfully makes one more playful. There are unhappier ways to be.
I imagine Zhuangzi as a playful sort of man, perhaps approximating his hypothetical sage who unites his heart with all other things and chariots on the back of every eventuality. He has hid his world in the world, where nothing can be lost. Thus, he is free to play. Thus he can roam "in our homeland of not-even-anything, the vast wilds of open nowhere", where he can “loaf and wander”, “doing lots of nothing”. That sounds like play to me.
A prerequisite to play is that it be optional; it is not required. Zhuangzi offers no truth, makes no claim that his way is the ‘right’ way; he only suggests that it may be an effective way to greater happiness should we wish to give it a try. This is not ‘serious’ business. Cosmic implications do not loom. In freeing himself from the belief that any one way must be the ‘true’ way, he frees himself to enjoy his way without distressing over whether it is right or that others follow other ways.
Play requires a bit of seriousness; that’s part of the fun. But when our seriousness becomes serious, then we have begun to lose our awareness of how that it is just a game. The freedom of play requires that it remain ever-aware that it is, after all, just play.
You can check out Scott's writings on Zhuangzi here.