Self-confidence has been designated a requisite individual characteristic for advancement in the workplace. Historically, self- confidence has been associated more with men than women. As a result, research on self-confidence in the workplace has been conceived within masculine behavioral paradigms under a guise of gender neutrality. The purpose of our study is to expose potential social and contextual factors not broadly examined in the extant literature on individual self-confidence in the workplace. Utilizing a problematizing approach, we developed two research questions: (1) what are the contextual and situational factors of the organizational environment that positively influence women’s self-confidence?, and (2) what are the contextual and situational factors of the organizational environment that negatively influence women’s self- confidence? In our analysis of qualitative survey results of a sample of 299 women professionals, we found that meso-level (social) and macro-level (organizational) factors contribute to women’s experience of self-confidence in the workplace, in addition to micro- level factors, that receive the bulk of scholarly attention. We propose that individual factors interact with social and organizational factors and support or impinge upon the attainment of self-confidence in the workplace. We include recommendations for further study.