Successful transition from education to the workplace is vital for young people, particularly Indigenous students from remote communities, to support their long-term economic and emotional well-being, social inclusion, physical and mental health. This paper reports findings from a three-year study undertaken collaboratively with young people at a remote Aboriginal boarding school. Motivated by the theoretical constructs of Indigenist theory and Funds of Knowledge, this research centres the voices of Aboriginal peoples. A team of Aboriginal and non-Aboriginal researchers worked "with" young Aboriginal people at the school to develop the method, to collect, and then analyse the data for this strengths-based qualitative study. Currently enrolled young people engaged in yarning with the participants, namely those who were past students from the school. This made it possible to gather stories to better understand the experiences, strengths, and motivations of Aboriginal young people from remote communities and the issues, constraints, and challenges faced when transitioning to life beyond the classroom. The findings highlight what can be improved to prepare Aboriginal people from remote communities for the workplace and for life beyond school--including their existing strengths and knowledge, aspects that occur within the parameters of the school, employer roles, skill development, and enablers of job and life success.