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This chapter explores perspectives on the role of leaders in higher education to promote wellbeing that strengthens capabilities and capacities and provides means for sustainable achievement and flourishing. The author discusses perspectives on health and wellness and approaches to wellbeing, flourishing, and thriving to find and create work–life balance and addresses training and development to enhance knowledge on the importance of wellbeing. The chapter is based on a qualitative interview study on practices of wellbeing, flourishing, and thriving in educational organizations with a purposive sample of six higher education leaders in the USA, Canada, and Jamaica. The findings revealed that promoting wellbeing in higher education demands qualities promoted by leaders such as capability, capacity, and sustainability for success. The chapter concludes with a theoretical framework on educational leaders’ wellbeing, flourishing, and sustainability that can create opportunities for leaders’ to understand health and wellness in their institutions effectively.

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