This brief study serves as an introduction into exploring the existence of resilience and self-esteem in urban high school learning environments. Data collection stems from interviews and surveys of graduates of urban high schools, who transitioned into college or careers. Findings from this qualitative phenomenological research contains participant recommendations to the specific actions of educators, as well as ideas, or appropriate learning environments, to foster the resilience and self-esteem which contributes to student academic and social success, leading to adult personal and profession success. Implications of this research include the significance of consideration of the impact of teacher behaviors on student academic and social emotional success within the classrooms of urban schools.