The Radiance of Drift and Doubt is the sage's only map.
(Zhuangzi, 2; Ziporyn)
I have previously mentioned Paul Kjellbrg's contribution in Essays on Skepticism, Relativism and Ethics in Zhuangzi ("Sextus Empiricus, Zhuangzi, and Xunzi on 'Why Be Skeptical"). I have found this essay downright inspiring.
Sextus (160-210) was a skeptic of the pyrrhonian school. Pyrrho (360-275 B.C.E) is said to have "traveled to India with Alexander where he encountered gymnosophs, or 'naked philosophers', after which he is said to have exhibited a state of remarkable peace of mind through his refusal to pronounce anything good or bad." This is an intriguing factoid in itself.
Kjellberg contrasts Sextus' with Zhuangzi's skepticism and asks how they differ. But first, he indicates how they are both "soft skeptics" in that they do not deny the possibility of knowledge but simply the possibility that one can conclusively know the certainty of what one knows.
Thus, both make uncertainty a fundamental point of departure for their philosophical journey. And both decide to make of uncertainty a positive phenomenon. The decision is thus not so much to be a skeptic, for that seems to them a necessity of intellectual honesty, but rather to make of this unavoidable reality a means to peace, rather than despair.
Sextus suggests that in the suspension of judgment as to whether something is good or bad, death for instance, enables one to achieve a certain degree of peace (ataraxia). Zhuangzi makes a very similar argument in his suggestion that the fear of death may be entirely misguided; perhaps we are lost children who don't know the way home, or like the woman who wept inconsolably upon being taken captive in war only to have a complete change of heart upon becoming the Emperor's concubine. This relatively intellectual use of skepticism to achieve a degree of peace can no doubt be nourished and intensified, but Zhuangzi goes further; for him it is an invitation to mysticism.
The choice to affirm rather than deny the reality of our uncertainty suggests for Zhuangzi an opportunity to release ourselves completely into that very same affirmation. "Handing it all over to the unavoidable" is not simply an intellectual exercise, but a mystical one. And the consequences likewise go beyond a moderate degree of peace and into joy and thankfulness.
In this, we can also see how his way is a way of according with nature; it is an agreement with the way things seem to be. As such, it remains true to the uncertainty inherent in the human condition, for nothing needs to be true for it to 'work'. In the next post we'll look at how the working of Zhuangzi's skepticism differs from that of Sextus.
You can check out Scott's writings on Zhuangzi here.