This literature review confirms that, for all young people, including those with vision impairment, transition from secondary school to adult life is a period filled with challenges and complications (Konarska, 2007). For this reason, transition-to-post school has been well-researched. Yet, few studies have examined how adolescents with vision impairment are prepared for post-school life, how they transition, and how they partake in post-school life. Despite the provision of a disability-specific curriculum, ongoing support from specialist staff, and the design and implementation of individual transition plans, research has indicated that young people with vision impairment find the transition to post-school difficult, face social isolation, and experience high levels of unemployment and underemployment. Although many of these young people have the cognitive capacity to contribute to and participate in society, most encounter difficulties in the social world and the world of work that minimise their contributions and diminish their life satisfaction. This chapter reviews literature on the transition pathways of adolescents with vision impairment and identified difficulties within the world of work and the social world, including employer attitudes and concerns about hiring a person with vision impairment and initiating and maintaining friendships.