Competitive sport in Canada is experiencing a reckoning, with calls for a national inquiry as well as an imploding of conventional norms challenging the primacy of winning above athletes’ personal well-being and psychosocial development. Through the present study, coaches’ challenges and successes in creating safer and more inclusive sport spaces were explored. Nine competitive sport coaches participated in an individual pre-season interview, completed an in-season reflective portfolio, and took part in an individual post-season interview. From a story analyst approach, the central narrative theme of ‘it’s my responsibility to enact change’ was identified within the coaches’ stories. To create relatable and resonating findings, a storyteller approach was used to communicate the multiple meanings of the central theme as accessible creative nonfiction stories. Four composite vignettes were developed to detail the coaches’ developing critical praxes: (a) when is it okay to intervene?; (b) why am I still hurdling over barriers?; (c) burning out… it’s consuming me; and (d) breaking through… it’s necessary work. The findings build on previous research, demonstrating how a coach’s critical praxis constantly shifts on a continuum of awareness and advocacy. Moreover, the findings provide alternative narratives on the challenges and successes coaches may face as they restructure their coaching practice to become safer and more inclusive. Researchers should make further use of creative nonfiction stories as they can help coaches assess how they can become transformative leaders who critically reflect on social issues in sport and act in ways that support advocacy and empowerment.