Recruiting and retaining quality teachers in urban schools remains a significant challenge (Freedman & Appleman, 2008, 2009; Lee, Eckrich, Lackey, & Showalter, 2010). With a quarter of the teaching force leaving their classrooms after one year and almost half leaving within five years, teachers in high poverty, urban schools are even more likely to quit (Ingersoll, 2003, 2004). In addition, Donaldson (2009) found that White and male teachers were more likely to leave teaching compared to their female counterparts. While it is important to study why teachers leave the profession (Cochran-Smith, 2004; Kersaint, Lewis, Potter, & Meisels, 2007), we believe that studies on factors that motivate teachers to stay would also provide insights to administrators and teacher educators as they consider preparing, recruiting, and retaining teachers in urban school settings. In the present study, we (two teacher educators) collaborated with one White, male secondary English teacher, Charles (a pseudonym), in exploring his journey from the teacher education program through his fifth year of teaching in an urban high school. Through his critical reflections on his journey over the last seven years, Charles not only shared his challenges and successes, but also offered insights regarding teacher education and teacher retention in urban settings.