Strategies for understanding the effect of negative life events on the psychosocial development of youth have focused on the aggregate association between risk factors and poor developmental outcomes. However, there is a strand of research in developmental psychology that has pushed for understanding the contextual nature of negative life events; if we can reveal how adolescents make meaning of stressful and traumatic life events, we will better understand why some demonstrate academic and social resilience. To understand this meaning-making process, I embarked on a 2-year qualitative research study at an alternative high school in New England (USA). This case provides an account of this study from start to finish. I examine the particular challenges, and possible solutions that arose in the selection of the sample, design of a data collection strategy, and analysis of multiple data sources (narratives, interviews, and memory aids of 28 adolescents). I examine the issues that emerge when doing research in schools, especially with a population of adolescents who have experienced severe stress and trauma. I provide specific strategies, like drawing life-graphs, which can help in connecting the written narratives and interviews of participants.