We hypothesized that increased enrollment of female medical students and different priorities of the current generation of students would be important influences on the declining interest in surgical careers. Students scored statements on surgical careers on 5-point Likert scales regarding agreement and whether these statements encouraged them to pursue a career in surgery. Data were analyzed using the Mann-Whitney U test. Qualitative comments were iteratively coded using a constant comparative method. Nine US medical schools. A Web-based survey on the Association for Surgical Education server was e-mailed to medical students. A total of 1300 of the 1365 respondents stated their sex. The survey asked questions pertaining to surgical life, surgical residency, surgeons as influence, equity, family, and other influences. A total of 680 (52%) of the 1300 respondents were male. Men and women disagreed about whether surgeons lead well-balanced lives (68% and 77%, respectively) and saw this as a deterrent. A total of 35% of women (3% men; P<.001) were discouraged by a lack of female role models. Compared with students unlikely to study surgery, lower percentages of male (74% vs 65%) and female students (85% vs 58%) likely to study surgery agreed that career choice was influenced by their decision to have a family (P=.01 for men, P<.001 for women). Of medical students who agreed that their skill sets were compatible with surgical careers, similar percentages were likely (30% men vs 24% women) and unlikely (49% men vs 54% women) to study surgery. All differences between men and women were less apparent when students likely to study surgery were compared with students unlikely to study surgery. The decision to have a family was a more significant influence for women than men, but family and lifestyle priorities were also important to male students, supporting our hypothesis that generation and gender are both important influences on career choices.