ABSTRACT Women are under-represented in high-performance head coach positions throughout global sport. To shed light on why this under-representation exists within UK swimming, an autoethnographic account of the first author’s experiences as a woman who competed and coached in high-performance swimming over a thirty-year career is presented. Critical reflexive conversations with the second author, coupled with sourcing artefacts such as memories, photographs and emails inspired four evocative personal stories that chart the voyage of: 1) a child entering and aspiring in the sport, 2) the transition from a retired female athlete to novice coach; 3) progression in becoming an international coach, and; 4) reaching the pinnacle of a coaching career and then beginning a coach tutor role. Accounts of how gender as a relation of power was exercised and navigated during the inauguration and progression as a woman who coached in a patriarchal profession are offered. In the pursuit of winning Olympic medals, an unrecognised double bind was revealed to have been negotiated throughout the entirety of the coach development pathway whereby masculine ideals were uncritically reproduced within the cultural landscape of elite UK swimming. Bourdieu’s concepts of habitus, capital, field and doxa offer analytical insight for how masculine norms were socially reproduced. This double bind is argued as having and continuing to impede women coaches’ progression towards achieving equality within high-performance settings like UK swimming. The study highlights the value of acknowledging socio-cultural factors in coach education to address gender imbalances at an elite level.