Research into men’s health has found that the potential conflict between health awareness and masculinity centred on paid work has been replaced by men’s understanding of health as a competitive edge in working life. In contemporary organisations, being healthy, demonstrating high performance and expressing a willingness to participate in workplace health promotion voluntarily promote one’s career. This chapter describes men’s agentive encounters with health-related social expectations in Finnish working life. The study focuses on how and why men care for their health in the context of work. The material consists of 18 interviews of men concerning work-related self-care. The study shows that the most prevalent aim of self-care was personal wellbeing, understood as a situation in which most areas of life are enjoyable in a sustained way. To this end, the men coopted disciplined practices that aimed to change or maintain certain qualities of the body and mind. However, this goal of personal wellbeing was supplemented by an aspiration for a balance between work and non-work. The majority of participants felt that self-care was addressed repeatedly in both the workplace and in the media. When participants co-opted recommended practices, this was done critically and for the sake of personal benefit. Thus, the study shows how men practice resistance when they navigate expectations surrounding working life. Concurrently, the participants perceived masculinity as more broadly defined and less binding than before. Besides contributing empirical data to the literature on men’s health, this chapter challenges men and masculinity scholars to focus their analytical gaze on men’s agency.