This paper is an exploration of the multiple realities of women’s work experiences in coaching and athletic management positions. Eleven women who had previously coached or directed women’s athletics programs were interviewed using a semi-structured approach. Three general categories emerged from the data — Support, Gender Differences, and Change. The work experiences reflect problems the women encountered at work, how organizations can be empowering, and the impact empowered women can have on the social construction of work. Based upon the data, we suggest that the individual search for empowerment takes different forms, yet also acknowledges that systemic changes must take place in order to improve the work environment for women. These findings are significant because they validate women’s experiences and contribute to the understanding of work experiences of those who are underrepresented and often left out of key circles of power and control.