Recent studies have highlighted high incidences of anxiety and depression amongst working musicians (Jacukowicz, 2016; Vaag et.al, 2016; Detari et.al, 2020), with psychosocial features of the contemporary working environment cited by some as a key contributory factor (Gross and Musgrave, 2016, 2017, 2020; Loveday et.al, 2022). Despite these reported challenges of musical work, music education within Higher Education (HE) has never been more popular, evidenced in the growth of courses dedicated to music, music production and music business management (Born and Devine, 2015). This popularity has consequently led to an increased interest in how music graduates manage their transition from education into the music industries (Bartleet et.al, 2019; Bennett et.al, 2018; Ghazali and Bennett, 2017). This chapter builds on this literature by asking; how meaningfully are music graduates being prepared for the emotional challenges they might face in their careers? By presenting personal reflections as an educator working within music and entrepreneurship education in HE in the United Kingdom, this chapter offers thoughts around how to best prepare students to enter a working environment typified by poor mental health outcomes. By considering curriculum-based opportunities and challenges – and asking questions as much as promising to answer them - this chapter contributes towards existing scholarship concerned with graduate transitions into the creative industries as well as pedagogical developments within music education.