In this paper we draw on stories of schooling as told by three transgender secondary school graduates. The study does not aim to be generalizable or ‘speak’ for the educational experiences of all Australian transgender-identifying students. The study is framed by first person articulations of what a trans-positive educational experience might involve. The paper leverages a life-history approach in which the participants rearticulate the influence that cisnormative school environments and media practices had on their transition timeframes. Throughout the life-history interviews conducted in a focus group, the participants considered the concept of how a trans-positive educational approach could be deployed in schools to develop services and resources that align with the findings of the National LGBTIQ Health Alliance, 2020.