Borrowing from paradoxical leadership literature and using the case of a social enterprise formed from a traditional nonprofit, the present study identifies a set of multilevel skills that helped the leader address the two social–business tensions, namely, continuance as a nonprofit and the forming of a social enterprise and the sustenance of a social enterprise and preventing the drift towards a for‐profit orientation during the formation of social enterprise and in its sustenance thereafter. The individual‐level paradoxical leadership skill of balancing idealism and pragmatism, the organizational‐level paradoxical leadership skill of navigating organizing contradictions, and the societal‐level skill of gauging societal developments and their organizational implications helped address the two different manifestations of social–business tensions during the formation and sustenance of a social enterprise. Implications for paradoxical leadership, social–business tensions, and social enterprise literature are discussed.