Native youth have complex schooling experiences. To better understand Indigenous youths' experience in public schools and in order to inform schooling practices and teacher preparation for both Native and non-Native teachers we share this portrait of Shayla. Through this research, particularly in the use of portraiture to document "goodness" in the lives of Eastern Band of Cherokee Indian youth in schools, a more complicated picture of success and challenges for Native youth emerges. We particularly highlight Shayla's experience in seventh and eighth grades in a rural middle school adjacent to the Eastern Band of Cherokee Indian Qualla Boundary. One finding suggests a need to better contextualize and understand students not only as individuals but also as members of families and cultural groups by non-Native teachers. Specifically, teachers must be aware of the historical and cultural significance of the place in which teaching and learning occurs in order to be culturally responsive. In sharing Shayla's complex experiences of schooling we hope to contribute to the ongoing discussions in teaching and teacher education about culturally relevant schooling for Native youth.