The purpose of this instrumental case study was to chronicle high school students' creative experiences in a songwriting course. Ten students in Grades 10-12 composed original songs, learned to accompany themselves on keyboard and 'ukulele, and performed their songs in class and at a coffee shop. Data sources consisted of classroom observations, semi-structured interviews, a focus group interview, student journal reflections, and songwriting artifacts, which provided insight into students' decision-making over the course of one semester. Of particular interest were the intersections between students' musical backgrounds and interests, and the learning processes they navigated while developing and performing songs. Overall, participants' continual negotiation of the songwriting process led to heightened self-actualization and responsive collaboration. Students highlighted musical goals, personal struggles, and collaborative episodes as meaningful turning points throughout the songwriting process. Implications include exploring creativity-focused school music offerings and promoting musical autonomy among students and teachers.