Whilst disability policy in Ireland has advanced in recent years, the under-representation of people with a disability in the workforce continues to be a social and economic challenge. Education and training have been identified as critical factors enabling a move into paid employment yet little is known, in an Irish context, as to the experiences of people living with disabilities as they transition into work. This qualitative study explores the views and perceptions of a diverse group of people with disabilities who are attempting, or have already made, a transition from education or training to work in the context of fluid 21st century labour markets. Key issues identified in the research include self-perceptions of work-readiness, concerns related to disability disclosure and the need for more flexible approaches to work-place accommodations.