The decrease in well-being of school leaders has become an area of concern among scholars and practitioners around the world. Globally, increasing social, political, economic, educational, and professional demands faced by school administrators have led to an unmanageable workload, stress, burnout, and a lack of work–life balance. However, some principals thrive amidst challenges and are recognized by various national and international awards as outstanding school leaders. Examining the challenges that award-winning school principals face can both prevent conditions that decrease their well-being and help understand coping strategies and support systems necessary for successful school leadership. Our study examined the sense of flourishing among the national award-winning principals in the Canada’s Outstanding Principals (COP) program that recognizes outstanding contributions of principals in publicly funded schools. In this article, we describe participants’ perceptions regarding the significance of principal well-being, barriers and challenges to their well-being, coping strategies to promote and sustain their well-being, and necessary policy and school system supports for enhanced principal well-being.

Given the intensification of school leadership roles, often resulting in heightened levels of stress, increasing workload, and ever-expanding challenges, it is important to understand how school leaders attend to and grow their own wellbeing as well as that of those they lead and work with. Our exploratory study examined the sense of flourishing within the professional lives of school headteachers from England’s “Growing the Top” outstanding schools, a program led by Challenge Partners. This article details participants’ perceptions of overall flourishing through its constituent constructs: flow, thriving, resilience, grit, and wellbeing. Our findings indicated that flourishing for England’s outstanding school leaders was a complex phenomenon, not helped by the current backdrop of challenges that school leaders in England are experiencing, with positive correlations in varying degrees among the constituent constructs of flow, thriving, resilience, grit, and wellbeing.