This essay begins by examining Hannah Arendt’s meditations on labor, work, and thought in The Human Condition (1958) and The Life of the Mind (1978), in order to probe the relationship between representations of work and the work of literary composition in Virginia Woolf’s first novel, The Voyage Out (1915). I argue that these two female intellectuals exhibited a shared concern for exploring the nature of the peculiar “work” of the imagination as analogous to, and importantly distinct from, other kinds of labor. Turning to The Voyage Out, I show how the novel dramatizes this relationship between labor, work, and authorship within the context of the contradictions inherent in its fictionalized imperial setting. Examining The Voyage Out in light of the later Arendt’s thought thus offers an opportunity to uncover the ambivalence at the heart of an early modernist experiment regarding the extent to which labor—particularly domestic and feminized labor—is or should be equatable to the work of literary production. I conclude by suggesting that reading Woolf together with Arendt illuminates the development of modernist critiques of mechanized and alienated labor, their relationship to modernist aesthetics, and an ambivalence at the core of such literature and theory about the activity of intellectual life.