In this dissertation I examine the perceptions of the experiences that first-language Cherokee speakers had of their school experiences, and of the higher education or career choices that they made beyond high school, in relation to their lack of English skills when they began school. While much research has been conducted on Native people who were sent to far-off boarding schools, a need to capture perceptions of those who attended English-speaking schools close to home was evident. This oral history methodology captures the stories and perceptions of four Cherokee speakers and examines their elementary school experiences in context with their careers and their progeny. Through lenses of transculturation theory and hermeneutic phenomenology, the essences of each are described and examined, challenging previous notions that Native children who succeed do so in spite of their cultural identity rather than because of it. Implications are determined for educators, administrators, and policy makers and how these perceptions of experiences can inform more culturally considerate teaching and school experiences for Native and other minority children.