Background. Very little research has been conducted with self-employed music teachers in North America. Research studies pertaining to music education have focused on the work of institutionally-employed arts educators working in the public or private school systems. However, many music teachers work in forms of self-employment due to the lack of traditional forms of employment available. The purpose of this study was to understand the work, artistic engagement, and lived experiences of music arts teachers working in forms of self-employment. This study expands on the work of Gross & Musgrave (2020), who explored the work and well-being of professional musicians in the United Kingdom. The overarching question that informed this study was, What is the nature of self-employed music educators’ work and well-being?Theoretical Frameworks. Elder’s life course perspective was used to analyze diverse lives in connection with the intersection of historical events, structural and social change, human agency, and social interconnectedness. This perspective was combined with Seligman’s (2011) PERMA theory of well-being comprises positive emotion, engagement, meaning, positive relationships, and accomplishment. Together, these frameworks were used to understand participants' employment patterns. Methodology. A constructivist grounded theory qualitative design was chosen for this research to expand our limited knowledge about self-employed music educators' work in Canada. Participants for this study were music, drama, dance, and visual arts teachers working in forms of self-employment. However, the focus of this paper is on self-employed music educators. Participants were recruited through conservatories and private studios. 9 self-employed music educators participated in this study. Results. 4 distinct employment patterns emerged from this research, Arts Educator Entrepreneur, who earned their entire living through arts teaching, Creator Performer Arts Educator who combined teaching with performing and other artistic pursuits, Arts Educator Post-Secondary Student, a teacher who was enrolled in a post-secondary program but continued to teach, and boundaryless career arts educator who combined teaching with other forms of self-employment employment within the arts or other fields. Results of this study indicate that participants with some business training or better equipped to navigate the challenges associated with self-employment. Participants with familial support were more equipped to navigate business challenges associated with self-employment. Conclusions. Post-secondary Music programs should consider providing some form of business training to help prepare students for diverse careers in music. This would allow students to explore career options that pair well with music teaching and performing.