Drawing on the views of a wide range of theorists, including in particular Greene, Greenfield and Habermas, the author argues for the need, if we are to conceive of new possibilities for ourselves and for society, for imagination. In this context, a persistent theme of rural communities, once heavily dependent on a single economic resource, surrounds the need for innovative leaders who are capable of imagining new options and willing to take considered risks. Based ona case study of a single community and its school, the author argues that these characteristicsare becoming the first victims of an everincreasing technological rationality of educational institutions, but that the process may be reversed by practices of communicative discourse, and by a revitalization of critical participation in the practical and performing arts. An underlying assumption is that successful school leaders consider the interests of adults as well as those of students, and that they, together with other community members, engage in decision-making on socioeconomic and cultural ends as well as means.