This article aims to present the issues involved in the passage from youth to adult life in the context of the Youth Qualification Project, a pilot project created by the Association des centres jeunesse du Québec (ACJQ). The trajectories observed among young people are fertile ground for examining the stakes of socio-professional insertion and qualification in the most disadvantaged populations. For these groups, in which those at risk find themselves excluded from their majority, the pilot project’s analysis of experience paths highlights the importance of the role of support figures, acting as allies, guides, and crossing guards for these students as they make the transition to adult life. The analysis suggests the necessity of seeing the passage to adult life as being composed of multiple, intimately related transitions, and to consider insertion as a multiplex process that young people can only understand in a compartmentalized way.