Although women and girls are making a space for themselves in sport, the underrepresentation of women coaches and findings within the literature suggests that women continue to challenge the historical connection between gender, power and masculine hegemony (Bougher et al., 2021; Theberge, 1984). Underrepresentation of women in coaching can often be attributed to external, social, and structural barriers, such as hiring from principal similarity, unequal assumptions of competence, microaggressions, homophobia, and a lack of role models (LaVoi et al., 2019; Norman & Simpson, 2022). The purpose of the current study was to understand the women coaches’ journey by exploring the facilitators and barriers that affected their progression in leadership roles within the sport system. Using a retrospective interview procedure in tandem with Côté and colleagues’ (2020) Personal Assets Framework, a spectrum of 13 engaged and 7 disengaged model women coaches were identified and asked to reflect upon their unique leadership experiences. Following a two-phased interview approach, a thematic analysis indicated that intrinsic motivations of growth facilitated coaching career progressions, supportive mentors, and a passion for the sport. Additionally, the coaches discussed many barriers such as doubt from male colleagues, cost of travel, the bias of organizations and colleagues, and being disregarded for positions and opinions.