This paper aims to discuss the coherence and consistency of the Stoic and the Nietzschean “art of dying at the right time”. Throughout this paper, we will use this expression to refer to the Stoics’ and Nietzsche’s treatment both of involuntary and voluntary death, inasmuch as both seem to be strongly connected to and grounded on the notion of timeliness. Taking this notion as a guiding thread, we will emphasize the several similarities that link their approach to suicide. Indeed, as will be shown, it is plausible to assume that Nietzsche’s understanding of voluntary death is particularly influenced by the Stoic tradition. At the same time, we will point out the relevant differences that make these two approaches differ. In dealing with the Stoic and the Nietzschean attitude towards suicide, the underlying question will be whether the legitimization and defense of voluntary death is compatible—and if so, to which extent—with their teachings, in particular, with their notions of happiness and affirmation of life, on the one hand, and their ideals of living in accordance with nature and amor fati, on the other.