Charles and Annie O'Connor have four children: Eileen, Mary, Charles and Francis. In 1904, the family moves to Sydney, where Charles finds work as a bookkeeper with Anthony Hordern & Sons. Initially living in Surry Hills, the family relocates to Redfern. Mary attends the nearby Sisters of Mercy school, while Charles and Francis attend the local Patrician Brothers school. Eileen’s attendance at school is irregular due to her handicap. Eileen and Mary are enrolled at Mount St Bernard at Pymble, a boarding school conducted by the Sisters of Mercy. Eileen finds the amount of movement required between the classrooms, refectory and dormitory too taxing and returns home, where her father provides home tuition. Despite just three years of formal schooling, Eileen proves to be a persuasive speaker and a prolific writer.