Background: Globally, there is a disparity that exists between equal employment opportunities for people with disabilities post-schooling. While South Africa has aimed at the inclusion of people with disabilities, there has not been sufficient evidence of a successful transition from school to work environments.Objectives: This study documents the experiences and barriers that influence the preparation of high school students with disabilities for post-secondary education and work opportunities.Method: A qualitative research methodology employing multiple case study design was used where semi-structured in-depth interviews were conducted with youth between the ages of 18 years and 36 years who were currently employed. The participants were identified through purposeful sampling. Data were analysed by thematic analysis.Results: The findings indicate two overarching themes indicating that the career choices of participants, firstly, were significantly influenced by teacher and guidance counsellor expectations and, secondly, experiences of discouragement where personal agency and autonomy were limited.Conclusion: This study illuminates the need to enhance the decisions around careers for people with disabilities which should debunk the expectations of society.Contribution: This study will make teachers, mentors and counsellors more aware of their contribution, influence and support to youth with disabilities as they transition into the workplace.