With the increased participation of women athletes and the growth of women's college sports teams and programs since Title IX, it would seem that this trend in participation would be translated into a golden opportunity for women to advance in athletics careers as coaches and administrators. Yet, while the opportunity for such career advancement would seem available, women remain underrepresented in these areas, particularly in key leadership positions where much of the decision-making about women's college sports get made. Such underrepresentation by women in college coaching and athletics leadership poses a problem for women in sport and has been the subject of numerous research studies. What has not been sufficiently studied, however, is the decision-making that women engage in as they consider whether or not to pursue or to continue careers in college athletics as coaches and administrators. Through in-depth interviews with current and former coaches and administrators, this study provides a greater understanding of the underrepresentation of women in athletics leadership from the perspective of the women in, and most likely to fill, those positions.