This chapter presents an alternative theoretical framework that expands current understandings of self-determination in post-school transition planning for students with disability. Achieving successful and productive post-school transitions has developed into a social inclusion trend that is evidenced in the discourse and policy of many developed countries. However, more recent literature on youth aspirations has criticised this conventional approach to raising aspirations for and participation in post-compulsory education, as it fails to recognise important links between young people's aspirations and their access to social, cultural and economic resources. Likewise, research shows that people with disability have continued to experience significantly poorer post-school outcomes and fewer opportunities for self-determination than their peers, leading to social exclusion and marginalisation through no choice of their own. Thus, re-imagining aspirations for people with disability can be a crucial step to afford new insights into post-school transiting planning that can pave the way to a more inclusive and democratic society.