Purpose – The purpose of this paper is to analyze the effect of gender upon the relation between protean and boundaryless career attitudes and subjective career success, in today’s dynamic and changing organizational context. Design/methodology/approach – Data were collected using a questionnaire conducted on 150 graduate and post-graduate distance learning students. The data were analyzed using structural equation modeling. Findings – The analysis indicates that women’s career success is positively related with self-direction and negatively related with their reliance on their own values. Furthermore, the authors found a negative relation between organizational mobility preference and men’s subjective career success. Research limitations/implications – A potential limitation of this study is that all participants were distance-learning students, thus limiting the generalizability of the findings to other populations. Furthermore, cross-sectional designs do not permit drawing conclusions regarding the causal direction. Practical implications – Organizations should transform work structures and human resources policies and provide career models that allow women flexibility and more control over their work. Research results show that values-driven predisposition may lead to low levels of perceived career success. This indirectly suggests that individuals experience intrinsic career success when their values are consistent with organizational values, and therefore they should seek work opportunities in organizations whose aim, scope, and philosophy is consistent with their ideals. Originality/value – This is the first paper to shed light on gender’s impact upon the relationship between protean and boundaryless career attitudes and subjective career success, in a context in which there have been calls in literature for more career research taking into account gender differences.