In the increasingly complex world of college choice, high school counselors are an important resource for college-bound students, yet the environment these counselors find themselves in is one that focuses on questions of value and return on investment, resulting in the elevation of some academic disciplines over others. Using a multiple case study design and Eisner's criticism and connoisseurship method, this qualitative study seek to describe how college counselors at Arizona School for the Arts guide prospective music major through college and major choice by exploring how counselors' backgrounds predisposed them to guiding students through college and major choice, their perception of the value of a music degree, the significance of their predisposition and perceptions for their guidance of prospective music majors, and the surrounding influences that impact their work. Immersive participant narratives and rich description are used to present complexity and nuance while interpretation and evaluation are woven throughout. Themes derived from a synthesis of the narratives are presented with recommendations and opportunities for future study. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]