As women secondary school principals navigate their career paths and manage their work-life roles, they encounter varied obstacles and barriers requiring them to shift, pause, restart and maneuver to reach their goals. The purpose of this qualitative study is to capture an understanding of how women secondary school principals in British Columbia, Canada have navigated the paths to their current roles. The study is important because there is a dearth of information regarding the experiences of women secondary school principals in Canada, and this interpretive interview study positively contributes to the literature base. The data collected was through semi-structured interviews with eleven women secondary school principals. Through open and axial coding of the interview data, common themes emerged regarding career path experiences: career goals and decisions, supports and mentors, gendered expectations, and factors related to being a woman. Findings show supporters, mentors and networks are integral as women strive for and become secondary school principals. Additionally, the findings indicate relationships at home and work are key factors in the strategies women principals utilize to facilitate the management of their work and life roles. This study also highlights the systemic barriers mired in white male dominated expectations the participants were required to traverse to meet their own needs and seek the supports they required to reach their goals. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]