The Zhuangzi is a book that opens to a virtual wilderness of interpretive possibilities begging for exploration by scholars and laypersons alike. What follows here is an adventuresome foray by one of the latter. As such, it is essentially an exercise in creative writing. Since it is our interpretive conclusion that this was precisely what Zhuangzi himself was about, we believe he would smile broadly upon this endeavor however far-afield its proclamations might be. This point is central within this essay. However we engage with Zhuangzi, whether as a dilettante or an academic, it is the engagement that matters most. Conclusions are secondary at best. This having been said, conclusions will be found herein. Ambiguity is the signature characteristic of Zhuangzi’s writing. Awareness of ambiguity as a defining characteristic of the human experience invites us to consider the importance of not-knowing, the thing-left-out, the usefulness of the useless, the prioritization of Yin over Yang, and, most importantly, the experience of inherent emptiness. For Zhuangzi, such an awareness invites a radical paradigm shift away from the cognitive to the visceral. It invites an embrace of emptiness that renders one free of all dependence on being a self in need of itself.