From the Philadelphia Award Records [3081]. 

Born in Philadelphia, Bailey was educated entirely in its schools and universities.  Graduating from the Philadelphia High School for Girls in 1916, Bailey hoped that a scholarship to Radcliffe College would serve as the springboard to a successful writing career.  “In those days families didn’t like to let their daughters go away from home,” Bailey recalled, “so I went to the University of Pennsylvania instead and fell in love with it.”  Bailey majored in education because it was the only area of concentration open to full-time female students at the university.  In 1931 she earned a Master’s of Science degree in Education.  Bailey began her 43-year career in the Philadelphia public schools teaching math at the High School for Girls.  She rose steadily within the administrative hierarchy, from department head of mathematics and then vice principal at Roxborough High School, to principal of Stetson Junior High.  After completing a special assignment on curriculum development, Bailey returned to Girls High as principal.  She was later promoted to superintendent of School District 6.  In 1953 Bailey was promoted to Associate Superintendent of Schools in charge of curriculum, instruction, and teacher education.  Bailey knew of only one other woman in the country holding the position of associate superintendent in a big city public school system.  She distinguished herself in this role with her innovative efforts in teacher in-service training.  Bailey believed that “the broad cultural background acquired by the teacher in college isn’t enough.  There must be on-the-job training.”  This training included after-school courses for teachers, and an emphasis on continual teacher self-improvement, whether after school, on the weekend, or in the summer.