Whiteside graduated from Shortridge High School and entered the Indianapolis Normal School in 1922, when in training as a cadet teacher she met the teachers who became her best friends and Founders of the Sorority. She taught school until 1951 when she retired and later helped her husband to develop a business. She also started her own millinery business and worked with her church and various organizations. After the death of her husband she ran their business from 1955-1957 and returned to teaching in 1959 where she remained until her retirement in 1970.