[4] In 1917, Douglass began working as a stenographer for John Eugene Diggs, one of Norfolk's few African American attorneys.
She passed the bar examination in 1926, and became the second African American woman admitted to practice law in Virginia, and the first Black female lawyer in Norfolk.
During the 1940s, Douglass served two terms as Virginia vice president of the National Association of Women Lawyers.
[10] During World War II, Douglass was a volunteer with the all-black Norfolk Auxiliary of the American Red Cross Motor Corps.
[11] She served as general counsel for the Norfolk Association of Real Estate Brokers, an organization that worked to combat housing discrimination towards African American families.