Entrepreneurship- the process of transforming ideas into enterprises that create financial, social, and/or artistic value- is a label used to categorize the skills and mindsets needed to self-curate a successful career in the arts. Whether wrought via opportunity or necessity, entrepreneurship has emerged as a practice that can empower music educators to address inequities, build collaborations, bolster advocacy, and innovate transformative solutions to challenges they identify in the field. Interest in the application of entrepreneurial ideals and practices to music, education, and the arts has steadily grown over the past 30+ years, with courses, centers, institutes, and degree programs in music and arts entrepreneurship now numbering in the hundreds at colleges and universities internationally. Prior to this institutional codification, entrepreneurial thinkers shaped music education for generations-dreamers like Shinichi Suzuki, Carl Orff, Jose Antonio Abreu, and Julia Ettie Crane. Yet, we know little about how this spirit develops through postsecondary music education, and whether differences manifest in the perceptions and outcomes of music teachers who pursue an entrepreneurial path. Therefore, the purpose of this study is to examine the educational antecedents, career conditions and outcomes, and demographics of active P-12 music educators who engage in entrepreneurial activities within the arts simultaneous to their teaching jobs. The data source for this study is the 2022 North American survey of arts degree alumni produced by the Strategic National Arts Alumni Project (SNAAP). This survey was distributed to 120 postsecondary institutions, with over 61,000 alumni responding. Respondents answered questions about their satisfaction with their educational experiences and subsequent careers, perceived skills development, and other elements of their educational and professional histories. Applying several filters to the full SNAAP survey dataset resulted in a final analytic sample of 72 active P-12 music educators who indicated that they also worked freelance or as an independent contractor within the arts or design. Descriptive and inferential analyses revealed a range of findings concerning high-impact practices that foster entrepreneurialism, perceived skills gaps that should be addressed to better meet the needs of these entrepreneurially-minded teachers, and differences in career outcomes when comparing these teachers to those who are less entrepreneurial. Specifically, entrepreneurial music teachers were significantly less satisfied with many aspects of their undergraduate education; slightly more satisfied with their earnings, opportunities to be creative, and overall job satisfaction; and significantly more likely to utilize creative thinking, problem-solving, and adaptability in their work.