After the First World War, the second generation of headmistresses were working in a Britain in which the secondary education of girls was generally accepted. In 1920, Phyllis Monk, a former Blackheath student and Roedean teacher, was appointed to take charge of Chorleywood College, a new secondary school for girls with a vision impairment. She became a pioneer in special education for girls, but triangulating personal with school and national records demonstrates the challenges Phyllis faced in ensuring Chorleywood's survival. She had to deal not only with the financial difficulties and technological limitations of the interwar years, but also with societal constraints, which illustrate the nexus of class, gender and disability. As a head, she was a pioneer and wrote her own book about her school, creating discussion of her presentation of her own role.