This qualitative case study of successful educators in one urban high school investigated: How do veteran urban teachers wrestle with the decision to stay or leave teaching? If and how can we conceptualize their considerations in light of a theory of courageousness? Using philosophical foundations and a framework of ordinary courage (Brown, The gifts of imperfection: Let go of who you think you're supposed to be and embrace who you are. Hazelden, Center City, MN, 2010), findings indicate that there are multiple “push” and “pull” factors—almost all linked to educational policies—with which teachers wrestle while contemplating leaving the classroom, and their willingness to confront and discuss these factors marks them as potentially courageous. Implications for research, policy, and practice are presented. © 2014, Springer Science+Business Media New York.