This chapter considers the pathways to becoming an artistic social entrepreneur. Previous research on social entrepreneurs has emphasized the impact of one's stock of human, social, and cultural capital on one's mobilization of requisite resources for launching and sustaining a social enterprise. Less sociological attention has been given to the influence of career-biographical factors, such as family, religion, education, and pivotal career turning points that may inspire and compel one to become a social entrepreneur and to envision and shape one's social enterprise, let alone an artistic social enterprise. The profiles of four artistic social entrepreneurs in this chapter illustrate how their strategic and risk orientations and career pathways shape the social enterprises they envision and influence their assumption and enactment of their roles as artist activists.