The Water Reckoning project was initiated to involve young people, teachers and academics in a creative project, which drew on Dorothy Heathcote’s philosophy and strategies, in particular that of Rolling Role. The idea for the project began at IDIERI 7 when Pam Bowell proposed the initiation of an international collaboration that would focus on revisiting Rolling Role through the use of digital communications and platforms. The goal was to have the project culminate at the Heathcote Reconsidered conference in London. The project resulted in five educational and research sites being involved from Australia, Greece, Singapore, and the USA. This paper will provide an overview of the project and the Rolling Role concept and how it was applied to the development of the Water Reckoning project. It will also explore initial learnings that have emerged from the project at each site. It concludes with some implications for creating Rolling Role work within contemporary school systems and possibilities for the future.