In this qualitative study of middle school English teachers, I investigated the phenomenon of why teachers stay, year in and year out, despite challenges brought on by educational reforms and negative depictions from the general public. The teachers’ experiences illustrate the dedication and perseverance of professionals committed to working with students year in and year out. I framed this case study (Merriam, 1988) in theories of sensemaking (Maitliss & Christianson, 2014; Wieck, 1995) and critical pedagogy (Freire, 1970; Giroux, 2011). The participants were three teachers who taught middle school English for over ten years. Within this time frame, they were exposed to multiple, ongoing reforms: No Child Left Behind, Race to the Top, and Common Core State Standards. I used sensemaking and critical pedagogy lenses to explore how these teachers experienced issues of power and interpreted educational reforms. I also examined the reasons why they persisted in the profession. I employed grounded theory (Charmaz, 2006; Glaser & Strauss, 1967) and Gee’s (2011) Seven Building Tasks for analysis to identify four categories to illuminate the teachers’ stories: 1) Public Perception of the Profession, 2) Pedagogy and Curriculum, 3) Relationships, and 4) Being a Teacher. The teachers’ experienced ongoing struggles and yet had longevity in the profession. Implications of the study point to the perils and promises of long-term teaching. The perils were challenges of the profession: demands from administrators, new and limiting curriculum, a negative public perception, and long hours. The promises these teachers kept were commitments to decision makers and the public, middle school students and their families, and to the profession. It is these promises that they kept each year that motivated the teachers and sustained them over time.