In many schools, both urban and rural, children living in poverty face daily stressors including lack of parental support, lack of resources, unsafe living conditions, and poor nutrition. As teachers are first responders in facing these difficult situations, resilience enables teachers to overcome challenges and succeed professionally. Teachers who have been found to be more resilient tend to feel more successful and stay in their positions longer. Teachers at varying experience levels have different approaches to maintaining their resilience in response to daily stressors. The purpose of this comparative case study was to compare the resilience factors of an early career and a late career music teacher within high-poverty, trauma-sensitive contexts. Participants exhibited varying levels of resilience by adapting their expectations to their school context and maintaining a positive attitude.