This work investigates the complexity of ethics as a field of inquiry and practice across a principal’s career. Fully contextualized, and thus carrying the contradictions and requirements of any school, the issues realistically do not usually lead to a single, beat-all answer, as any solution will likely have positive and negative consequences. Drawn from the authors’ experiences and studies of schools over decades, the central figure is a fictional principal of a magnet school, whose dilemmas reflect the questions educators must be prepared for. Each decision takes into account the principal’s and staff’s identities and values because they are all human and their opinions influence the outcomes. The work injects analytic, virtue, feminist, care, deontological, and critical theory insights as Deweyan ethics provides a lens for examining dilemmas. This accessible work blends reflective theory, the ordinary worlds of schools, and engaging pedagogical practice to guide those planning to enter the education sector.