This article examines the ways in which Gipsy Hill Training College's (GHTC) graduates represented their lives and work in the college magazine, the "Gipsy Trail". The so-called "Wraggle Taggle News" featured snippets from married and single women teachers at every stage of their lives and work in Britain and overseas by the late 1930s. It will be shown that graduates integrated discourses of the modern woman and Gipsy Hill's modernist ideals of individual autonomy, and educational and social progressivism into their paid work and domestic situations, leisure and propaganda work across their life course. Indeed, it was a case of "once a teacher, always a teacher" and everywhere a modern woman teacher in the interwar years. (Contains 142 footnotes.)