The purpose of this study was to examine pre- and in-service female band teachers' perspectives regarding their experiences in realizing their professional goals. Domains guiding this inquiry included (a) gaining entry into the profession of band teaching, (b) navigating the profession, and (c) gender issues. Findings from this multiple case study indicated that numerous outside factors affected the career paths of the participants, resulting in all of the women pursuing elementary, middle, or multi-grade level jobs. These factors included (a) the positions available at the time of the initial job search, (b) family responsibilities, (c) the perceived time commitment thought to accompany high school band teaching positions, and (d) the desire to witness musical and social growth in students. Some of the participants believed the band profession was increasingly welcoming to women; however, several of the participants reported challenges of being a woman in band teaching. These challenges included the struggle to network with those perceived to be in power, fitting in at professional development events, and gaining respect from students and colleagues. Although some of the women found their gender could be an asset, they also found themselves restricted by social constructs and stereotypes of gender.