This article focuses on the degree that "students' aspirations" (educational and occupational) are linked to or affected by their working status, and other personal or family characteristics. By drawing data from a larger cross-sectional study of the social and educational profile of students in primary and secondary education (ages 7-18), carried out in the Dodecanese region, in two phases (1995-96 & 2001-02), it examines the relationship between high school employment and the educational and trajectories of youth, as it is mediated and influenced by various personal ("e.g. gender") and family ("e.g. parental occupation") factors. Its main merit is the provision of comparative data from a country on which there is no research on youth employment to date, and the corroboration of a series of research findings at international level, relating to adolescence, adolescent employment and the school-work link. Before analysing the main data, a short description of the international bibliography on the particular issues is given, and a brief background on the research carried out in Greece about the youth employment is outlined.