Being a woman in the outdoor learning profession can bring distinctive challenges and roadblocks. Even more difficult is sustaining a life-long career, flourishing into a woman's 50s or 60s. Based on this premise, career longevity seems elusive for some women who aspire to work in the outdoors. This paper analyses the autobiographies of three experienced Australian female outdoor educators who have successfully navigated careers in the outdoor profession. Four key emergent themes were identified in the women's life histories that included: orientation towards the outdoors; decisions and motivations for entering the field; career opportunities; and challenges. Their narratives exemplify the accomplishments of women with distinguished careers in the outdoor profession and highlight various manifestations of burnout. Finally, the findings shed light upon factors that allow women to achieve career longevity.