Aboriginal school students, especially those living in rural and remote areas, continue to achieve below the national standard in oral language, literacy and numeracy. On leaving school their unemployment rate is three times that of non-Aboriginal people. At the same time we know academic and career success is closely tied to one's self-identity. Therefore, the aim of this research is twofold: firstly, within the context of living in a rural community, explore which factors contribute to a positive self-identity amongst Aboriginal youth; and secondly, examine how this relates to their educational experience and transition into the workplace. The participants were five Aboriginal males aged between 16-18 years at the commencement of the study who attended the local high school and were supported by Clontarf Academy staff who were located at this school. The data were collected over an 18 month period using observation, formal and informal interviews (i.e., yarning). This was done from an 'inside' perspective as one of the researchers had a long term mentoring relationship with all the participants. This rich and thick data was used to formulate in-depth, ethnographic case studies which were further interrogated to identify themes to address the research aims. The findings show that 'family' play a key role in the maintenance of both language and culture, that style of communication continues to be strong marker of Aboriginality, and their location in the rural area and particularly as part of the Academy served to support and sustain strong Aboriginal identities.