This paper will explore the relevance of Sunderland Church High School for Girls in understanding the life and beliefs of Eileen O'Shaughnessy. It will take account of education reforms, and look at how the influential head teacher, Miss Ironside, instigated changes in the school that benefited Eileen and led to her studying at Oxford University before working in London. The love of education that Ironside instilled returned to Eileen in the early 1930s and contributed to her enrolling on an MA which in turn led to her meeting Eric Blair. The skills and resourcefulness that she started to develop at Sunderland Church High set her in good stead to survive as a single woman in the 1930s. Drawing on archive material, the paper will show how Eileen embraced school life, and how her teachers perceived and encouraged Eileen in her formative years.