For all young people, transition from secondary school to adulthood is a period filled with anticipation and challenge. Adolescents with vision impairment experience some unique and specific difficulties associated with their disability and their ability to operate in society (Konarska, 2007; Rosenblum, 2000). Notwithstanding the provision of a disability-specific curriculum, ongoing support from specialist staff, and the design and implementation of individualised transition plans, these young people find the transition to post-school life difficult, face social isolation, and experience high levels of unemployment and underemployment. Despite these poor post-school outcomes, few studies have examined how adolescents with vision impairment are prepared for post-school life; how they transition out of secondary school, how they plan to participate in post-school life, and how this transition process can be enhanced. Primarily, the study presented in this thesis aimed to capture the perspectives of adolescents and young adults to provide insights into the influences and experiences related to the critical transition. The perspectives of these key stakeholders were augmented by the views of school staff and parents. In this qualitative study, carefully sequenced and systematic methods were used to gauge participant perspectives. First, adolescents with vision impairment (n = 5) were invited to generate daily journal entries of their lives at secondary school over a 4-week period in response to set prompts. Following journal writing, the researcher designed interview procedures (i.e., an interviewer script and interview items) based on the study’s aims, along with data from journal entries and relevant literature. Second, one-on-one interviews were conducted not only with these adolescents, but also with young adults (n = 5) who had lived the post-school transition. Third, school staff (n = 6) and parents (n = 3) participated in separate focus group discussions in order to collect their perspectives about this transition. Prior to analysis, data from these three sources (journal entries, interviews, and group discussions) were transcribed and the resultant text coded into themes, sub-themes, and categories using NVivo8 software (QSR International, 2007).