This article examines the potential contribution of social enterprise to the "wicked" problem of creativity and literacy in a performative schooling environment, drawing on an ethnographic study of Ciento, a social enterprise organization that works with under-resourced young people, families, and communities in Melbourne, Australia. In light of the growing body of research on the ways in which schools navigate creativity and performativity, this article contributes new knowledge on non-school organizations that is largely missing from this conversation, as well as new insights on the operations of education-focused social enterprises in Australia. It considers the social, political, and historical factors that have shaped this unique space of educational "wickedity" and the ways in which organizational rationales and practices, as well as the experiences and views of staff and participants, indicate a complex, promising, and innovative approach to educational problem-solving.