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While health in the workplace has been paid considerable attention in management research, one category of workers has been left in the shadows: executives. With this in mind, this paper explores executives’ work by focusing on the paradoxes that define it. The aim is to gain a better understanding of the relationship between the executive’s health and the company’s health. The methodology is both quantitative and qualitative. The quantitative study emphasizes a positive correlation between the executive’s and the company’s perceived levels of health. Four configurations of this relationship are highlighted, of which two mark a possible disconnection between the health of the executive and the health of the company: a "protection zone" (the executive is fine, but the company is undergoing major difficulties) and an "overheating zone" (the executive is struggling, but feels that the company is doing well). The qualitative study unveils four paradoxes that are linked to the work of executives and may impact their health: relationship to time, relationship to size and growth, relationship to stakeholders, and relationship to oneself and to the entrepreneurial project. Finally, we also analyze the ways in which executives go about managing these paradoxes.