This study investigates teacher stress, anxiety, and burnout through my experience teaching music in a suburban Toronto secondary school between 2002 and 2008. Primary data sources include a rich collection of journal entries I have written over a six-year period, which were retrospectively analyzed in this study. Hence, this study is principally rooted in reflective practice. In addition, this study is informed through autobiographical and phenomenological lenses. These other two lenses have allowed me to incorporate secondary source data (anecdotal notes, emails, text messages, and video footage) that were repurposed for this study. Findings have exposed two principal thematic representations from the data, namely; (a) those that directly or indirectly addressed extracurricular performances, and (b) fear of failure. Re-experiencing my experience has been exceedingly therapeutic and cathartic for me, providing insight and transparency into the demanding nature of music pedagogy at the secondary school level. In addition, findings have helped me to refine and develop my current and future pedagogy as a teacher educator.