It would be true to say that all parents face transition points in their child’s education with much trepidation and concern. For parents of a child with a disability transition from school to further study, training or employment is particularly distressing. The interventions multiply, the directions are never clear and there often appears to be a lack of coordination, communication and delay in establishing support services. Understanding the need for independence into the adult learning world while you have had years of interdependence and interventions from experts can leave parents in a dilemma as how best to help and assist their child. How can their transition experience be successful and establish them on their career development journey with the skills and confidence they need to navigate the maze? Through personal recollections and current experience this workshop will aim to examine some of the issues that face students and young adults when disability support services are not seamless. It will offer suggestions on how tertiary institutions, academics and disability support services can develop flexible and supportive services that focus on career development rather than specific operational strategies.