This paper examines the hidden challenges experienced by individuals with special needs during the transition years between school and work. An assessment framework is proposed that covers domains of difficulties, developmental tasks during the transition years, the matrix of support within the home-community-institutions ecosystems, and the individual's personal profile of schooling experience, academic attainments, interests, aptitudes and sense of self-determination. The paper ends with a model for intervention addressing self-efficacy and the social cognitive environment of the individual.