Mobility is essential in navigating familiar and unfamiliar environments. People with disability may experience vulnerability in navigating the external environment, when mobility is hindered by discomfort, commodification, or disorientation. Independent commute, choice, and control can be enhanced with appropriate aids, technology, and infrastructure. Self-determination can also be seen to enhance mobility through the realisation of strengths and limitations of the individual and the opportunity to act with self-regulation, in a way that responds to events in an empowered way. Utilising a critical incident technique, this qualitative study examines the enabling and disabling factors that impact self-determination of young adults with mobility disability in the context of their journey to work and explores the role digital technologies can play in this journey. Key findings related to the importance of mobility planning, transport options and communication in the journey to work are discussed. The importance of digital technologies is highlighted including the proposed features of digital enabling platforms.