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The first woman to become superintendent of a major city school system, Ella Flagg Young was an advocate for teachers throughout her long career. A reform-oriented leader in the Progressive movement, Young worked closely with John Dewey at the University of Chicago, earning her Ph.D. when she was 55 years old. She led the Chicago schools during a tumultuous period when progressivism warred with industrialization as a model for education. Her tenure as superintendent was marked by a number of reforms, but also by conflict with the conservative Board of Education.

Ella Flagg Young graduated from the Chicago Normal School and began teaching in Chicago in 1862, when she was 18 years old. Her career in administration began 3 years later when she was appointed director of practice-teaching classrooms. During the next 14 years she served as a high school math teacher and as principal of two Chicago schools. Young's reputation as a democratic leader grew as she encouraged her teachers to develop their own teaching methods and established faculty study groups to enrich the curriculum.

In 1887 Young was promoted to assistant district superintendent, a new position in the rapidly growing Chicago system. In this position she continued her democratic education practices, including popular teacher institutes on a variety of topics. Young herself often led the institutes, but she also invited faculty from the pedagogy and philosophy departments at the University of Chicago to speak. She used the institutes to advance her ideas about democracy in education and encouraged teachers to take an active role in shaping curriculum. The Chicago Teachers' Federation, organized in 1897 and the first teacher advocacy organization in the United States, was started by teachers who had been influenced by Young's ideas.

Her tenure as assistant district superintendent ended in 1899 when she resigned after a conservative and autocratic superintendent was appointed. She left the school system and went to the University of Chicago to study with John Dewey in the new Department of Education. Within a year she had completed her Ph.D. and joined the faculty. Young's dissertation, published in 1900 as Isolation in the Schools, laid out the stark contrast between the industrial model of education, with its clock-driven mechanization and rigid bureaucracy, and the humanistic and democratic Progressive model. Dewey later said that during Young's time at the University, she acquired a theoretical base for the ideas she had developed earlier through practical experience. In return, Dewey learned how the theories he was developing at the University actually translated into educational practice. Young remained at the University as a professor of education for 5 years, administering Dewey's Laboratory School, editing a journal for teachers, and developing new courses. She left the University in 1904 when John Dewey's philosophical conflicts with University President William R. Harper led to his resignation. Dewey went to Columbia University and Young went abroad for a year.

In 1905 she returned to Chicago as principal of the Chicago Normal School, where she put into practice the reforms and scientific approach to education espoused by Dewey. Young restructured the Normal School and improved relations among the faculty, students, and community. Her pragmatic approach to education stressed content as well as pedagogy, and she cautioned her teachers to be concerned with both what students learned and how they learned it.

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