Background: Few studies have examined whether women and men identify the same factors as important in choosing their specialty. We sought to evaluate whether the factors influencing residents' choice of surgical specialty differed by gender. Study Design: A 32-item Web survey, designed to elucidate which factors motivated residents to seek fellowship training, was sent to 99 graduates of a university general surgery program, all of whom matriculated between 1985 and 2006. Results: A total of 74 (75%) respondents replied (16 women, 58 men). There was a higher proportion of men who pursued fellowship training than women (69% versus 38%, p = 0.04), but there was no significant difference in those who were currently in academic practice (men, 46% versus women, 27%, p = 0.2). Both genders were equally likely to respond that interest in and intellectual appeal of their field, clinical opportunities in that field, and having an influential mentor during residency were important in choosing their future specialty. But significantly more women listed lifestyle as an important factor in choosing their future careers (69% versus 43%, p = 0.03). When respondents' data from the most recent decade were analyzed, there was no difference between genders in completion of fellowship training or in those in academic practice. But lifestyle continued to be more important to women. Conclusions: Both genders were influenced by many similar factors when deciding to pursue subspecialty training, but women were more likely than men to be influenced by their perception of the lifestyle associated with their career choice. These findings suggest that general surgical residency programs might improve efforts to recruit women by addressing the perception of the lifestyle associated with choosing a surgical career. © 2007 American College of Surgeons.