This thesis explores three themes: North Indian classical music, the individual Alif Laila, and the philosophical connection each has to improvisation. The process that was followed to analyze the interactions between raga in the North Indian classical tradition and one well-known musician's path within that tradition bridges theory with individual insight. Alif Laila is the individual at the center of the study. As a prominent professional sitarist living in the Washington, D.C. region, her input is analyzed placing focus on individuality within the life of a traditionally trained musician living and teaching in a Western context. Her expression in traditional sharing of musical knowledge from teacher to student, in raga performance and in musical philosophy expand upon the new generation of teacher/performers who translate their craft in order to continue their tradition of North Indian classical music. Improvisation, both as a social and musical design, extends the scholarly research and personalized ethnography to complete the thesis.