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Guided by personal encounters with violence including death, homicides, and incarceration, four authors comprising a teacher, social worker, and two community activists, unveil their 20-year+ advocacy journey in the Jane and Finch community in Toronto, Canada including involvement with programs through the non-profit organization Youth Association for Academics, Athletics, and Character Education (YAAACE). The conversations are examined through an intersectional and Critical Race Theory lens through duoethnography as a methodology. Overall, the article contributes to filling in the research gap by centering racialized personal narratives in the Canadian context, offering nuanced lessons for integrating research and activism, and showcasing tangible ways to support the needs of youth and families through community-oriented, trauma-informed approaches.