Abstract This qualitative autoethnography explores how and why youth succeed and struggle in their personal and academic lives, through the lens of my own successes and struggles. Autoethnography as an analytical tool places value on the self-reflexive process of understanding. By working through my own childhood experiences and development as a person and a learner, I explore how my personal understanding of trauma impacts my methods for teaching the survival-based students who I now mentor as teacher. This study provides educators, therapists, and caregivers with a deeper understanding of trauma and resilience, from my personal experiences and professional analysis and application. Readers can implement insights from this study to guide young people towards an individual reflection of their experiences. This dissertation is a serious attempt to discover directions for success with trauma and behavior issues in schools. The different data sources and analysis techniques fit together to demonstrate how the experiences of childhood transition into the outcomes of adulthood. Most importantly, by shedding light on the intervention process, we can increase the odds for today’s struggling young people. This thesis travels chapter by chapter, alternating between memoir and analysis to ultimately conclude that lagging executive function skills can be strengthened through behavior intervention which will ultimately increase individual resilience.