While conducting a qualitative, semi-structured interview study that investigated the role of program administrators and managers in the field of teaching English to speakers of other languages (TESOL), the author encountered a TESOL professional whose 30-year career as an instructor, administrator, and owner of her own language school was so inspirational as to warrant its own exploration as a continuous professional development case study. Using the conceptual framework of continuous professional development (CPD) through the lenses of critically reflective practice and transformative and transformational learning (Brookfield, 2017; Cranton, 1996; Freire, 2007; Mezirow, 1991) and the methodological framework of the use of narratives in TESOL and teachers' narrative inquiry as professional development (Johnson & Golombek, 2002; Pavlenko, 2002), the author unravels each step of Sophie's career as a guidebook for other TESOL professionals who might be contemplating a similar journey. The author's findings highlight the impetus and decision-making processes behind each transition in her career trajectory and concludes by illuminating what Sophie identified as lessons learned. Since many TESOL professionals aspire to open their own language schools in an English as a foreign language (EFL) context, the lessons learned from that enterprise were delineated separately. The critical roles preservice preparation, CPD, and effective supervision and mentorship play when transitioning into administrative positions were identified as areas for further investigation and research, including how modifications in these areas might foster a more seamless professional evolution into entrepreneurship.