Despite working many hours under stressful conditions, surgeons report high levels of career satisfaction. However, female surgeons report lower career satisfaction and are underrepresented in some surgical fields. The goal of this analysis was to explore how gender influences career satisfaction for pediatric surgeons working in male-dominated subspecialties using a qualitative approach to inquiry. The grounded theory method of data collection and analysis was used. Forty-two surgeons from nine countries were interviewed using teleconferencing technology about how gender influences their career satisfaction using a semistructured interview guide. Transcripts were coded line by line, and codes and categories were created using an inductive approach to inquiry. All surgeons in this study described their careers as satisfying; however, a paradoxical tension emerged whereby female surgeons reported that they experienced no gender bias while simultaneously reporting clear instances of discrimination. All surgeons reported biases against women including instances of sexism, gender-based discrimination (i.e., unwillingness to hire women, encouragement to leave the profession, etc.), unequal distribution of labor for parenting/domestic work for women, and a lack of adequate accommodations and policies for pregnancy, birthing, and breastfeeding. The qualitative methodology used in this study revealed deep complexities of the experiences of female surgeons and the ways in which these experiences contribute to or detract from career satisfaction for female surgeons. Implications of our findings are discussed, and several feminist and psychological theoretical frameworks in which to understand the processes and complexities of career satisfaction for female surgeons are presented in the discussion.