Contemporary agendas of high-stakes accountability initiatives, national and international competitiveness drives, and standardized curriculum policies have significantly influenced the work of principals. This article explores how these changes influence the work of Ontario principals in English-speaking public schools. We know the changing nature of principals’ work, as compared to the work of teachers, has not been as well represented in the literature and research. Over the last two decades in Ontario, school principals have had to deal with sweeping reform measures that have re-engineered and reconfgured the educational terrain of school administration and leadership. This article takes a broad approach to understanding what contemporary principals do. Among other things, it acknowledges the wide-ranging, diverse and complex nature of what principals do. Most importantly, it adopts the concept of ‘work’ to explore principals’ worlds. While the study in this article utilized a mixed-methods approach using interviews and school site observations, findings reported in this article come from the principal interviews only. This article focuses specifically on changing student demographics, information and communication technology, and health and wellbeing