With research pointing to increased levels of stress and work demands on school leaders, attention has turned to examining the factors that contribute to their well-being. Studies have also shown that many school administrators not just survive but also thrive in their work and succeed despite work-related challenges. Furthermore, some principals experience flourishing at work, which is characterized by optimal functioning, feeling good, and achieving a balanced life. Our study examined the sense of flourishing of the national award-winning principals in the Canada's Outstanding Principals program, which recognized outstanding contributions of principals in publicly funded schools. In this article, we describe the participants' perceptions in relation to the following constructs in the overall flourishing: flow, thriving, resilience, and grit. This study highlights the conditions, behaviours, mindsets, and characteristics that are critical for the well-being of school administrators.