Martin Heidegger famously declares that Dasein does not perish but experiences its demise, and that death stands before us as something to be anticipated. This idea of being-towards-death is an anticipation of possibility, of becoming authentically free for one’s death. If we take Heidegger’s view of death and compare it to that of the Daoist philosopher Zhuangzi, we notice that the latter also holds death in an unusual light. For Zhuangzi, death is possibility not because it symbolizes the perfection of being but insofar as it reveals its entanglements. This paper will thus argue in support of the Daoist notion that death is neither to be feared nor does it serve as the end of one’s contribution to the world. It will also take the stance that death qua nothingness is both a corporeal and metaphorical embodiment of Dao in that death and nothingness reflect the natural praxis of Dao to be still, empty, and quiet. In order to facilitate our analysis, we will focus on the story of Zhuangzi and the roadside skull, a story that has Zhuangzi pillowing said skull from which he realizes that life is but a pillowing of death.