Although the number of female entrepreneurs has recently increased, there is little research that has compared female managers and female entrepreneurs in their work experiences and conditions. Therefore, the aim of this study was to examine the potential differences and similarities between women in management versus women in entrepreneurship regarding challenges, motivators for entry, adaptations, gender roles, and self-monitoring. Data collected from 87 women in management and entrepreneurship showed that female managers faced gender biases more than did entrepreneurs and had to choose between their professional and their personal goals when deciding to have children. Motivators for entry into entrepreneurship were increased job autonomy and flexibility of schedule. Regarding adaptations, all managers and entrepreneurs changed their communication style according to an audience and relied on their social support systems to deal with household responsibilities and on mentors for professional issues. Lastly, entrepreneurs were higher self-monitors and more likely to be androgynous than women in management. There were no differences in adoption of a masculine gender role between the two groups. Results of the present study indicate that these two groups of professional women have similar as well as different experiences and conditions. The implications of these findings are discussed