There are two articles in Experimental Essays on Chuang-tzu that take Zhuangzi's unique application of the concept of play as their main theme. I won't make further mention of either here except to say that they have inspired this post.
The word "play" seldom appears in the Inner Chapters and then only at the whim of the translators. Yet, I think it represents an essential aspect of his philosophy as actually acted out in the world. His chosen word is "wandering".
What does it mean to "wander"? She who psychologically wanders fully engages in the normal activities of life, yet with an inner detachment untypical of the usual manner of that engagement. Typically, we do things because we perceive their outcomes as of significant importance. Success or failure becomes a matter of grave concern. Our very sense of self-worth can depend on the levels of our perceived achievements; we depend on outcomes. Zhuangzi's wandering, on the other hand, though it may pursue the same tangible goals, does not require any specific outcome. One does not depend on any outcome to derive a sense of worth or meaning; these are self-arising and non-contingent. Nor does one fear outcomes that may even threaten one's existence; there is, in the end, nothing to lose.
Zhuangzian wandering (play) is thus a kind of world-engagement free of worry; it is carefree living. One does one's best and follows along with whatever arises. Yet still this does not address the quality of positive enjoyment that play suggests. From whence does this arise? If we say that someone is carefree, does this not conjure up a vision of someone enjoying themselves? Why is this? For no reason. For to be carefree is to require no reason to enjoy oneself. Given the opportunity, this human experience seems to naturally express itself in enjoyment. To require a reason to be happy is to depend on something, is to make happiness contingent, and that is the dissolution of happiness.
I have taken “happiness” as my normative value. There are words that describe and categorize this valuation, but they are all abstracted from the actual life experience which, it seems to me, takes the enjoyment of life as its given. Happiness is not a goal of life; it is the expression of life itself. And like life, it has no ground, no raison d’etre, no need to justify itself; it simply is.
People speak of finding one’s purpose in life; ‘spiritual’ books propose to tell us how to discover our ‘true purpose’. No such agenda is ever considered by Zhuangzi for the simple reason that life itself is understood to be sufficient in itself. Zhuangzi assumes we prefer happiness because life is an impulse toward self-enjoyment. It is enough to let life express itself in us.
You can check out Scott's writings on Zhuangzi here.