From Aboriginal Australian perspectives and experiences, Aunty Judi Wickes and Marnee Shay bring a cross-generational, critical race analysis of Aboriginal identities and how they are implicated in the schooling experiences of Aboriginal young people. Using autoethnography, Aunty Judi and Marnee discuss their educational experiences in the Australian education systems from primary schooling experiences to university settings. These narratives bring forth the dominant discourses that continue to subjugate and subordinate Aboriginal Australians and Aboriginal Australian identities in Education settings. The paper distinguishes the narratives of two Aboriginal women and how on-going colonial and racialised constructions of Aboriginal identity continue to impact upon the educational experiences of Aboriginal peoples and consequently the engagement of Aboriginal young people in school settings. Moreover, we will use the process of critical self-reflection to re-imagine educational approaches to reconstruct our own experiences and consider what changes might improve the outcomes of Indigenous young people for future generations.