Building futures for young people in and out of rural places has been a perennial quest for those interested in education and youth studies . For rural youth, the opportunities education can afford usually necessitates leaving home to study in a regional or metropolitan campus, with added cost and loss for families and communities. Thus, aiming a post-compulsory education for rural students typically involves ‘higher stakes’ than for their urban counterparts. This chapter examines the impact of the view of education as ‘learning to leave’ (Corbett in Learning to leave: the irony of schooling in a coastal community. Fernwood Publishing Co., Halifax, 2007) against the backdrop of building the social fabric and sustainability of rural places. We explore this tension between the concepts of aspirations and belonging in young peoples’ lives and then consider the implications for changing (rural) teachers’ work. We argue that the tension between belonging and being aspirational, as it is articulated in educational discourse, is central on both individual decision-making and institutional responsiveness. We seek to problematise the relationship between belonging and aspirations by focusing on the impact that rural teachers’ work can have in (re)solving or (re)producing this tension. We draw on case studies in Victoria and Tasmania to examine how different communities represent structures of opportunity, and consider some related challenges and opportunities for rural education .