Playfulness is a quality that we can easily attribute to the thought of Zhuangzi. It can be found everywhere in the very medium of its presentation. Theories are espoused only to be turned on their heads. Horseheaded Humpbacks instruct us on the beauties of the Way. The Sage (Confucius) becomes the author of his own deconstruction. This is but a sampling; all in all, the entirety of the Inner Chapters becomes a philosophy of no-philosophy (Wu), a poking fun at contemporary philosophy to free us from every fixed philosophy. What makes this other than mere sarcasm or cynicism, however, is that this playfulness in the medium is a reflection of the message itself. Zhuangzi call us to a life lived in the spirit of playfulness.
Wu (The Butterfly as Companion) gives considerable space to an exploration of play in the message of Zhuangzi. He discusses how the qualities of play are reflected in many of his themes in ways that we might not immediately recognize. One such theme is "the usefulness of the useless". Play is useless in that it has no purpose other than itself. It is "autotelic"; it has no end beyond itself. Play is "self-forgetting", and in the midst of play takes no thought as to its usefulness. Needless to say, we can think of all manner of benefits to play, but when we do so we are not playing. When Zhuangzi tells us of the usefulness of the useless he is stepping out of the play, to invite us to come play.
Wu offers Zhuangzi's answer to Hui Shih's charge that his words are useless (like his useless tree) as an example of such an invitation. He also tells us that "by definition play cannot be defined" and thus if we are to 'understand' it, we must experience the 'spirit' of it. Here is Wu's translation of Zhuangzi's response to Hui — a powerful invitation to a spirituality of play:
Now you have a huge tree, worrying about its no-use.
Why not plant it in the village of not-any-existence,
the field of vast nothing?
Go rambling around and doing nothing beside it,
Roaming around and lying asleep beneath it?
Not dying young by axes, there is nothing to harm.
If there is nothing for which to be useful, how can there
be anything from which to distress and suffer?
You can check out Scott's writings on Zhuangzi here.