This paper examines two notions of possibility conceived by Kierkegaard and Zhuangzi respectively. Kierkegaard conceives of it with appeals to the feeling of anxiety, while Zhuangzi deals with it in terms of a type of aesthetic feeling. Based on these distinctions, the paper goes further to explore two types of human existence as fostered by these two corresponding concepts of possibility. According to Kierkegaard, in order to maintain a connection with possibility, which would provide freedom to human existence, one must have faith in the redeemer bringing back possibility so that an individual human being might renew his or her choice ceaselessly. Zhuangzi, on the other hand, advises staying in the realm of nothingness and letting go of all things to avoid being trapped by the struggle of discerning between good and evil.