The sustainability of careers has become a topic of relevance in the shift from a traditional concept of career to more self-directed, boundaryless careers. In this context, it’s recognized that, while employees manage their careers, organizations should support their development. The present study aims to analyze the dynamics of reciprocal relationships between two components of the primary indicators of sustainable careers, namely, well-being (i.e., purpose in life) and performance (i.e., organizational citizenship behavior), and the moderating role of gender on those relationships. Two hundred and nine participants responded to the questionnaire three different times. A reinforcing relationship was found between these variables for women when the spiral analyzed started with organizational citizenship behavior, whereas men did not show any of the proposed relationships. Therefore, this study enhances understanding of the different workplace experiences of men and women, their well-being, performance, and career development.
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