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This study has critically examined Freud’s and Derrida’s theories of mourning, focusing on Zhuangzi’s view of death, and has sought to elucidate the unique structure of mourning embedded in his thought. Freud explained mourning as a process of withdrawing and reinvesting the libid.o from the lost object, while regarding its failure as pathological melancholia. Derrida, however, criticized this dichotomous framework and understood mourning as an ethical practice of remembering the absent other and preserving alterity. In contrast, Zhuangzi does not conceive of mourning in terms of forgetting or mere remembrance; rather, he expands it into a philosophical reflection that integrates the generation and extinction of beings within a cosmological vision of qi 氣-transformation. Zhuangzi’s notion of mourning is characterized, first, by acknowledging and affirming the sorrow that accompanies loss; second, by enabling ontological reflection through the persistence of memory rather than through forgetting; and third, by dissolving the boundary between self and other in order to attain the freedom of the equality of all things (wanwu qitong 萬物齊同). Such a perspective does not regard mourning as rupture or pathological failure, but transforms it into an occasion for ontological conversion and philosophical practice. Moreover, Zhuangzi’s conception of mourning provides a new horizon of thought for contemporary experiences of loss and mourning culture. In particular, it presents an important implication as a philosophical alternative that seeks the affirmation of emotions, the internal philosophization of memory, and the restoration of reciprocal coexistence through the dissolution of the boundary between self and other.