The purpose of this study was to analyze the factors influencing women's decisions to enter male-dominated work environments, specifically the fields of academia, law, and Computer Sciences; In order to encourage more women to pursue nontraditional careers, it is necessary to determine the types of support and environments required for women to succeed in these areas. Therefore, qualitative, interpretive research within a feminist theoretical framework was used to assess the impact of family background, educational opportunities, and cultural expectations on the respondents' career choices. How the respondents negotiated the imaginary line between their personal and private lives, and how they handled the discriminatory roadblocks in their workplaces were also analyzed. Triangulation was used for data collection and analysis. Specific tools utilized included: in-depth interviews (quotations), direct observations (field notes), and written materials (documentation). Member checks were used to verify the data collected;Results from the interpretation of the data revealed that "glass ceilings" and gender discrimination still exist within these patriarchal work environments. Despite these obstacles, the women who participated in this study were able to succeed in their nontraditional careers by re-inventing their lives, defying gendered cultural expectations, and becoming indispensable in their fields through specialization. The implications for this research are far-reaching. Male-dominated work environments will become more equitable when sex-role stereotypes are minimalized in familial and educational environments, gender communication patterns are revised, and the corporate culture is restructured to recognize women's unique qualities and contributions.