The work‐family literature examines the degree to which work and family roles can be segmented or integrated by an individual. In the family firm, the requirement that work and family roles be integrated creates tension for family employees, particularly those who prefer higher degrees of segmentation between the roles. Integrating family firm with family relations research, this article explores potential difficulties experienced by family employees in making transitions from their family role to work role and the potential for family employees to engage in deviant behavior due to unresolved conflict and ambiguity from work‐family role integration. These difficulties, we argue, are in part due to problems in separating role expectations when they come from indistinct sources; that is, when the boss and father, for example, are the same person. We explain how the tensions between work and family can create a cycle of deviance in the family and family firm domains.