The purpose of this study is two-fold: to determine what external and organizational factors lead teachers in an urban, high-needs school district to consider leaving their teaching position or the teaching profession and to determine if perception of these factors differs among demographic groups of teachers. Access to high quality teachers is an educational opportunity issue. Urban, high-needs schools often have teachers that are less qualified compared to suburban schools, and this is exacerbated by poor teacher retention. Using a sample of teachers from an urban district, factors negatively affecting teachers' perception of their careers were identified. It was also found that teachers who are recognized for performance and hold leadership positions are more likely to stay in the profession.