The current population of young adults known as the Millennial Generation is the first generation in the United States who have always had access to listening to music via portable music players. This study was designed to explore and understand how listening to music in this mode may influence, change, and shape their internal worlds, in ways which may be of value to those psychotherapists who work with young adults. Research was conducted in two phases. In Phase One, quantitative data was gathered from 30, 18 to 22 year-olds who were recruited to participate in an online survey. Once this data was collected and analyzed, five participants were chosen to participate in an in-depth interview for Phase Two. These participants were asked several open-ended questions designed to further explore their personal experiences of listening to music via a portable music player. The findings of this study suggest that young adults’ portable music players can indeed function as transitional objects which not only assist them with emotional regulation, but also appear to serve them in other psychologically significant ways. The potential benefits of exploring the music clients listen to appears to be supported by recent research in several interdisciplinary fields and the idea was also unanimously endorsed by Phase Two participants. As a result of the widespread use of portable music players, especially among this generation, young adults now have the opportunity to share their experiences of listening to music, with their therapists, in the immediacy of the clinical setting.