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In today’s society, the growing norm of individualization places pressure on individuals to bring about favorable conditions for social integration, something that is no longer provided by major institutional affiliations. Biographical self-assessment and the ability to develop a “project of the self” are at the core of these new forms of socialization. In the field of employment, career development counseling services, which are supported by legal provisions, seek specifically to improve employees’ levels of autonomy by supporting their career repositioning. However, sociologists stress the ambiguity of this appeal to subjectivity, which can disempower the beneficiary while claiming to strengthen their autonomy. In exploring this hypothesis, the article shows that an instrumental framing of the subject’s biographical self-assessment has detrimental effects. By analyzing discursive practices from two different career development programs, it shows that referring to the principle of reality tends to restrictively frame interactions and prevent access both to subjective exploration and to the inter-subjective dynamics of the relationship.