The shifting meanings of work and leisure open up liminal spaces in the boundaries of both spheres of activity. In these liminal spaces, meanings and expectations around behavior are less crystalized and more open to individual innovation. When individuals attempt to transform an interest or a leisure activity into paid work, meanings related to both leisure and work threaten to delegitimize their activities. These spheres, like many activities, identities, ideals and other territories around which boundaries are drawn, are imperfectly compatible. I analyze the personal blogs and interview responses of ten lifestyle bloggers in order to examine how they protect their activities from threatening meanings. These individuals carefully navigate this disputed territory, employing monetary, emotional and relational strategies in order to satisfactorily balance enjoyment, autonomy and legitimacy. Their actions illuminate those of creative entrepreneurs negotiating modern work, and have implications for work on symbolic boundaries, modern work and economic sociology.