[2] Despite being uneducated and working in menial jobs, her parents, Hall and Bettye Estelle Massey, sent all of their children to college.

[1] Estelle received a teaching certificate from Prairie View State Normal and Industrial College (now Prairie View A&M University), but decided to move into nursing after she was nearly killed in a violent incident while teaching at a public school.

In 1934 she worked as a researcher for the Rosenwald Fund, then returned to Homer G. Phillips Hospital in St. Louis to become its first black director of nursing.

[3] In 1972 she taught at Central Nursing School of Lincoln Junior College in Kansas City, Missouri.

This marriage ended in divorce, and in 1947 she married Herman Osborne, public relations director of the United Mutual Life Insurance Company.