This article sets out to investigate the realities of the working lives of a small group of secondary school music teachers. More specifically, it focuses upon their views of the National Curriculum, Music Teaching as a Career, the Intersections between institutional roles and personal musical lives, and the Highs and Lows of teaching music. The central dilemma is seen to be the tension between the personal investment that music teachers contribute to schools, and the lack of recognition they receive in the career structure. The study concludes that we need to think radically about the future and be ready to re-define roles in order to generate fresh ways of working.