May studied under Brymner from 1907 to 1912, and twice, in 1910 and 1911, won bursaries from the Art Association of Montreal (AAM). She was later awarded the AAM’s Jessie Dow Prize in both 1914 and 1918. In the early 1920s she gave classes in her Montreal studio, which was that of the Beaver Hall Group, but her real career as a teacher began in 1936, when she accepted a position at the Elmwood private school for girls in Ottawa, where she settled. She also introduced art classes for children at the National Gallery of Canada in 1938.