Nyangatjatjara College is an independent Aboriginal school distributed across three campuses in the southern region of the Northern Territory. The College serves the Anangu (Pitjantjatjara and Yankunytjatjara) communities of Imanpa, Mutitjulu and Docker River. Since 2011, the College has conducted a series of student and community surveys aimed at obtaining feedback regarding students' educational experiences and their future aspirations. In 2016 Nyangatjatjara College funded a research project, Centring Anangu voices in Anangu education, to look more closely at Anangu educational aspirations in order to inform the development of a five-year strategic plan. Among other activities, interviewers conducted surveys by listening carefully to Anangu school students and community through sharing first-language narratives. This paper focuses on the most commonly discussed aspiration of students, their families and communities, namely, that school should enable young people to get a job. This finding parallels other research findings (Guenther et al., 2015) and the philosophical underpinnings of "red dirt thinking" on aspiration and success (Osborne & Guenther, 2013). Our examination of the data suggests that the theme of "work" is intertwined with aspects of the local community context. The paper concludes with an analysis of existing school-to-work transitions and opportunities, with suggestions for strengthening local participation in employment initiatives across the tri-state region at the intersection of the Northern Territory, South Australia and Western Australia.