Teaching can be incredibly rewarding and fulfilling as a career. Yet, we also know that the teaching profession is stressful and challenging with many demanding facets and realities beyond a teacher’s control. Moreover, research underlines that teacher wellbeing impacts positive student development (Granville-Chapman, 2021). So, how does a diverse school community underscore and build on commonalities to collaboratively work toward teacher and community-wide flourishing? Appleby College, an international day/boarding school comprised of forty-four cultures and nationalities, works to achieve this in our community through our everyday actions and interactions. We do this by intentionally focusing on five principles and practices in applied positive psychology and integrated elements of Granville-Chapman’s Model of School Leadership: leadership for teacher flourishing (2021). This allows teachers to feel empowered and enables them to develop and sustain their wellbeing and work toward community-wide wellbeing. Data collected through the COMPASS study, an initiative funded by the Canadian Institute of Health Research in collaboration with the University of Waterloo, will be presented and used as a basis for discussion. Stories of this work in action will also be shared as opportunities for growth and next steps forward.