From 1983 to 1994, she held senior-level positions at several Prince George's County government agencies, including executive director of the Consumer Protection Commission, and community partnerships director at the Department of Family Services.[3] In 1994 she was elected to the Prince George's county council, where she served for eight years. She was council chairman for two terms and vice chair for three terms.[2] After leaving the council, Bailey served as parent liaison for the Prince George's County Public Schools.[3]
In 2001, Bailey was elected to the national executive council of the Association for the Study of African American Life and History (ASALH); she is also president of the Prince George's County chapter. In 2002 she founded the Harlem Remembrance Foundation of Prince George's County, serving as its chairman of the board from 2003 to 2011. The foundation holds the annual Harlem Renaissance Festival, an idea Bailey conceived as a way to highlight the artistic and cultural contributions of African Americans during the Harlem Renaissance era, and to showcase the work of county residents who continue that legacy.[4] The festival draws thousands of visitors each year and features poetry readings, dance performances, visual art, and live jazz.[5] Notable performers have included actor Clifton Powell, who read the poetry of Langston Hughes, and jazz vocalist Jean Carne.[6]
Bailey was instrumental in the founding of several other non-profit organizations, including the LEARN Foundation (Landover Educational Athletic Recreational Non-Profit), the Kiamsha Youth Empowerment Organization, and the Royal Bafokeng Sister City Friendship Committee. She has also served on the national and local boards of the National Council of Negro Women.[2][7][8]