Performance success and positive development are goals of youth sport coaching that need not but often do find themselves in conflict with each other, yet there is a dearth of research that has inquired into the tensions between these 2 goals for sport coaches. Adopting an autoethnographic research design, this study explored the first author’s coaching experiences with a focus on his attempts to facilitate players’ personal development and the team’s performance success in a Canadian elite minor ice hockey context. Framed in a positive-youth-development approach, the first author’s philosophy and behaviors were informed by key tenants of achievement goal theory and self-determination theory. Three key areas were problematized: pursuing personal development and performance success, creating a task-oriented environment, and implementing autonomy-supportive behaviors. Practical implications for elite youth coaches and coach educations programs are discussed.