He married Dorothea Hope Geddes White in 1908; the couple had three children, Maurice, Margaret, and Christopher.[1]
During World War I, he served as a major with the British Intelligence Department of the War Office. In 1919 he was appointed headmaster of Christ's Hospital in Sussex, where he modernized the curriculum and authored several classical texts.
In 1930, he was appointed Principal of Queen's University in Kingston, Ontario, Canada. Fyfe had earlier expressed some disdain for the standard of education at 'colonial' universities, and so was recruited to improve the standards at Queen's. He had limited success in that task, since Canada was mired in the Great Depression, and funds were very scarce. But he did succeed in modernizing the curriculum somewhat, in raising the level of admission and scholarship, and in attracting increased prestige to Queen's.