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Mechanisms that lead to individual failure in professional pathways and the way they are resolved can be seen as a “black box” in management research. This article presents an analysis of individual failure in professional pathways which encompasses four dimensions: objective transactions, subjective transactions (Dubar 2015), identity tensions, and identity strategies. Six cases of failures and four identity strategies (manipulation of results, skills, blind conformity, and avoidance) were identified from a longitudinal study, based on eighty-seven interviews and observations of management accountants and banking advisors, within three organizations. Our research shows the importance of the relational and subjective dimension of failure, whose resolution requires the implementation of evolving strategies. Our interactionist and processual approach enables us to address the most hidden failures in organizations.