Women make up an increasing proportion of students entering the medical profession. Before 1970, women represented 6% or less of the medical student population. In drastic contrast, nearly half of first-time applicants to medical schools in 2011 were women. However, the ratio of women to men is less balanced among graduates from surgical residencies and among leadership positions in surgery. Less than 20% of full professor, tenured faculty, and departmental head positions are currently held by women. However, this disparity may resolve with time as more women who entered the field in the 1980s emerge as mature surgeons and leaders. The aim of this article is to review the history of women in surgery and to highlight individual and institutional creative modifications that can promote the advancement of women in surgery. A secondary aim of the article is to add some levity to the discussion with personal anecdotes representing the primary author's (ECM) personal opinions, biases, and reflections.