While many urban teachers flee urban schools after a few years of teaching, many spend their careers in teaching in the urban environment. A series of biographical interviews was conducted with four "career" urban teachers; throughout the data collection and analyses and despite their decade or more in the field, the interactions between the teachers' personal and professional lives emerged as an important theme and challenge. The following questions are addressed in this article: How are urban teachers thinking about the challenges and/or satisfactions of their work, and in what ways do the teachers' professional lives influence their personal lives? The perspectives of effective teachers who persist in the field can inform administrators about teachers' experiences, aid them in retaining more experienced teachers, and humanize the political discussion about school failure in the urban context.