Acting as an entry marker into the adult world, the transition from compulsory schooling is inextricably linked with a change in career status. As such, transition is widely acknowledged to be a significant event in the lives of all young people regardless of their dis/abilities. However, many dis/abled students in New Zealand, particularly those with high-end needs, experience many challenges in the construction and enactment of their career. These are often exacerbated by the limited availability of mainstream opportunities and/or the absence of clearly defined employment pathways. In addition, they are less likely to have had access to meaningful workplace experiences whilst at school which would assist them with the decisions they must make, and actions they must take in relation to their futures. In this article I locate the concept of the dis/abled student within a New Zealand context, critically explore the notion of career and consider whether this is a feasible and realistic aspiration for those with high-end needs. Following this, I discuss a case study of a post-secondary transitions scheme in the South Island of New Zealand which was established to meet the aspirations of students with high-end needs. This is used to illustrate how initiatives that seek to address the disjuncture between the desires of this student group, labour market expectations and the requirements of local employers can present both opportunities for change and challenges for inclusion.