Work is a semiotically oriented activity, that is, when working, individuals anticipate aspects of their activity using a network of signs and meanings and project themselves in time with the aim to achieve certain goals. This study proposes a discussion on the relationship between purpose and work and distinguishes purpose as objective, related to actions aimed at goals, and purpose as a glimpse or a hyper-generalized sign. Both of these purposes are related to other dimensions of an individual’s relationship, with their work that are not contained in their actions aimed at situated ends. From a methodological viewpoint, the arguments are developed based on the analysis of two fictional characters, inspired by the cultural psychology of semiotic orientation: Sisyphus, extracted from classical literature, and Bartleby, the scrivener of the novel of the same name written by Herman Melville. Based on this analysis, we propose considering the purpose–work relationship on two axes: (1) what articulates sense-meaning in the process of meaning-making, and (2) the axis of action potency and its relationship with the concepts of emptiness and contingency based on a human agent’s experiences in culture. The paper aims to contribute both to the cultural psychology of semiotic orientation and to the literature on the meaning of work.