In this chapter, the authors present data from participants about how legal prostitutes manage work and life boundaries. They argue that work-life management practices are different for stigmatized workers because they must cope with occupational stigma by segmenting work and life realms in acutely distinct ways. The data revealed that work-life boundaries are disciplined by legal mythologies and ambiguities surrounding worker restrictions, occupational ideologies of “work now, life later,” and perceived and experienced effects of community-based stigma. These legal, occupational, and community constructs ultimately privilege organizations’ and external communities’ interests, while individual dirty workers carry the weight of stigma.