The publication arises out of a research project of school education within South Africa and takes a school leadership perspective for imaginative possibilities resulting in school change. It illuminates the complexities associated with leading schools as they assume particular identities owing to specific categorizations. Its specific focus is on school leaders’ lived experiences of addressing school challenges that brought about substantive change to school life. The book chapters collectively build on personally, professionally, and socially useful understandings of teaching, learning, governance, school finance and school-community partnerships in relation to wider social, political and cultural concerns, and across diverse contexts. Drawing on everyday real-life experiences, generated mainly through a range of narrative and arts-based practices and sources, the book communicates new voices, new insights, and imaginative possibilities for working with school challenges in contextually relevant and responsive attitudes to bring quality education to the doors of schools. The book, therefore, foregrounds school leaders from school principals through to teacher leaders’ imaginative solutions to reimagining school life in each of their respective schools. Using a multi-perspectival theoretical lens, we offer portrayals of different dimensions of lived experiences of school life. The authors of the chapters (comprising both experienced and novice researchers) present critical descriptive accounts of different contextual realities of schooling juxtaposed against how they are categorized, for example: infrastructure (quintile rankings); financial (fee paying); geography (rural, urban, townships); poverty (feeding scheme) and performance.