The period 1974–1999 were transition years for government school systems in Australia and New South Wales (NSW), where government agencies issued numerous policies and documents to influence and manage education and resultant classroom pedagogy. During those years, many music syllabi were produced for enactment in NSW, placing multiple demands on teacher accountability. This paper forms part of a larger study involving three generations of music teachers representing different career stages and experiences and presents the voices of the group of experienced music teachers (EMTs), exploring the impact of syllabus change, teacher identity, pedagogical skills, and eventual flourishing as confident teachers.