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As part of a clinical approach in a psychoanalytic orientation, my research in education science focused on the “school drop-out process.” It analyzed teenagers’ relationship with knowledge, leading me to implement a unique research approach to understand this relationship. This article presents my experience as a researcher in setting up discussion groups for twelve- to fifteen-year-olds in schools near Paris. This professional experience, also involving personal aspects, led me to wonder about my subjective involvement and my counter-transference regarding both my object of study (relationship between knowledge and dropping out of school) and the target group (teenagers). This article presents a clinical analysis based on elements that questioned my own subjectivity as a “subject-researcher” and my involvement in relationships with teenagers. I argue that this analysis is essential to understanding what I call the “school drop-out process.”