A Chicago native born on the crossroads of working-class, Black and female, Shay Stewart-Bouley’s career since 1997 has focused on weaving these intersections into her daily life and professional work. Since the mid-1990s, Shay has worked in the non-profit sector, during the earlier years working primarily with marginalized groups in Chicago, including the homeless and women being exploited in sex work. In the early-2000s, Shay moved from her native Chicago to Maine and, as a Black woman living in one of the least diverse spaces in the United States, found herself writing regularly about race relations, social justice, and white supremacy in such publications at the Portland Phoenix (where she had a month column, “Diverse City” for more than a decade), the Portland Press Herald, the Journal Tribune, and DigPortland. It was also in Maine that her work shifted to non-profit administration, working both as an executive director at a small faith-based non-profit in Southern Maine and non-profit consultant/grant-writer to other organizations, then later becoming executive director of the oldest continuously operating anti-racism organization in the nation, Community Change Inc. (based in Boston), where she still works today, though she continues to reside in Maine.