Technical and vocational education represents a central formative component of high school education in Chile, encompassing nearly 40% of students, who fundamentally come from the poorest sectors of society, in the last two years of compulsory education. Such relevance, however, has not found a correlate in the development of policies aimed at strengthening the training model or articulating with the country?s productive needs. The record shows that TVE graduates have heterogeneous and especially complex life experiences. Structural factors linked to high degrees of social vulnerability and institutional inconsistencies present in school-to-work policies are part of the diagnosis of the situation. In this framework, the article addresses the tensions and the type of resources that young people use to face their immediate future once they leave PTE. Based on an analysis that combines contributions from life course perspective and the sociology of the experience (emphasizing the analysis of breakpoints and structural tests), it is possible to review the decisions, supports, difficulties, and challenges that these young people experience in their school-to-work transition. The effect of structural constraints and the ways in which these young people carry out their personal actions within a highly individualized context and with weak institutional supports, as in the Chilean case, are explored.