This symposium presentation will share insights gained from the presenter’s experience of leading positive education in two Australian school settings. The presenter will draw on learnings derived from leading the development and implementation of a whole-school approach to Positive Education at Loreto Toorak and then taking on the role of Head of Positive Education at Geelong Grammar School, a school 10 years into their Positive Education journey. This presentation will contribute to a broader discussion about how to develop, implement and sustain a whole-school approach to Positive Education in a range of contexts: the challenges school leaders will likely face and the strategies which can be utilised to overcome these challenges.