The article discusses how a peer group culture in the school setting, embedded in conflicting fields of work and education, co-constructs student disengagement. Disengagement is traditionally linked with dropout and engagement with completion, but the study shows that this relation is not so linear. The data are based on a field study, where the author was enrolled as a student in the car mechanic program in order to gain insight into the cultural and relational dynamics of dropping out through an autoethnographical approach. Awareness of the transformations that took place was used to understand the (in)appropriate ways of becoming a car mechanic student. The study reveals discrepancies in different criteria for being successful between students, teachers, and the workplaces. This points to the need to understand disengagement as context dependent and socially regulated, rather than as a function of the individual's attributes.