Brook Ziporyn, in his introduction to his Zhuangzi, summarizes one dimension of Zhuangzi's philosophy so succinctly that I will presume to reproduce it here, though it be a more lengthy quote than I usually share. He begins by stating that Zhuangzi sought to answer the question, "How should I live my life?"
Zhuangzi's answer to this problem, simply stated, is this:...our understanding consciousness can never know why it sees things one way rather than another, can never ultimately ground its own judgments, and is actually in no position to serve as a guide for living. To consciously weigh alternatives, apply your understanding to making a decision about what is best, and then deliberately follow the course you have decided on — this is the fundamental structure of all purposive activity and conscious knowledge, the basis of all ethics, all philosophy, all politics, all human endeavors at improvement, and this is precisely what Zhuangzi seems to consider ridiculous and impossible. Knowledge is unreliable; Will is unreliable; Tradition is unreliable; Intuition is unreliable; Logic is unreliable; Faith is unreliable. But what else is there?Zhuangzi's philosophy is intended to bring us to this precipice from which there is no way forward except to leap (though perhaps we might attempt a retreat into faith in the unreliable, that is, into unconsciousness). This is a leap of faith; but it is a faith devoid of all content, except for a fundamental trust that ultimately, all is well. Yet even this is secondary to the simple inevitability of this necessary leap. Anything else is a retreat into self-deception. Death is the seal of this same inevitability. Our fate is, quite simply, out of our hands. Zhuangzi's leap is an acknowledgment of this in life.
This leap could be called an act of surrender into the inevitable. This is what is meant by "opening (oneself) broadly into the vastness....abandoning (oneself) to it, even to the very depths." And this implies a great letting go. What is letting go? Releasing one's grip. On what? On life itself. On identity. On every false sense of grounded fixity.
What may be unique about Zhuangzi's vision is that it offers no new surety to replace the unsure. One does not leap from groundlessness so as to discover a true ground. No, it is the acceptance that one remains forever ungrounded. "The Radiance of Drift and Doubt is the sage's only map."
One can only wander.
Yet this wandering is a free and joyous experience. That which wants and requires surety has been left behind; all that remains is the experience of living, without need of purpose or answers.
You can check out Scott's writings on Zhuangzi here.