Concerned about the phenomena of early school leaving in our region, we are two teachers who initiated and developed a new school from the ground up to re-engage young people disenfranchised with schooling back into formalised learning. Using critical action research methodology over a three and a half year developmental period, this endeavour involved us in exercising particular dimensions of leadership to engineer a sustainable second chance school. Twelve years after its development, the school continues with enrolments of over 100 senior secondary students in recent years. The schooling justice work we pursued during the developmental period drew us into emancipatory leadership work that called us to be; (1) teacher activists embracing social entrepreneurial strategies imbued with (2) relational sensibilities, and (3) architects of socially just school design informed by (4) critical praxis within a university led professional learning community. The second chance school has re-engaged over 1000 students back into formalised learning since its inception and has offered pathways into post-school tertiary study, apprenticeships and training for the majority of these students.