Teacher professional learning and professionalism cannot be advanced via a singular focus on building core competencies, standards, knowledge, and skills alone. Never is this made more apparent than in Singapore, where a highly efficient and effective teaching fraternity has been nurtured over the years through centralised policy-making but where increasing attention has been paid to the importance of holistic development and individual student wellbeing. Alongside this policy shift, we argue for a more holistic and dynamic view of teacher professionalism that considers the values and moral foundations of teaching. Teacher resilience must be seen as a social practice that is context dependent and realised through a process of coping and appraisal. Building on social cultural and cognitive theory, our multiple-case study examines the stories of professional growth written by two school leaders almost a decade ago together with more recent interview data via the narrative inquiry method. Our findings indicate that their professional identities and practices as teachers and school leaders were deeply grounded in student-centric values formed in their beginning teacher days and in ways that enhanced their professional excellence and growth. The need for research, policy, and practice that prioritise emotional wellbeing and the development of the whole person is also discussed.