This article follows the movements of educational imagination articulated by the late scholar of religious education Maria Harris to offer musings on academic leadership that attempts a decolonial turn for enduring change in theological education. With stylistic and thought experimentations, the essay identifies challenges besieging administrative leadership amid a global pandemic, shifting institutional and cultural landscapes, and enduring legacies of colonial, racial, and gendered regimes. Harris's educational esthetic and theories of learning and change leadership frame insights for a decolonizing and diasporic consciousness for today's religious educator who administers and leads with educational imagination.