Scientific studies, focusing on positive and/or meaningful media experiences evoked by any form of the media (e.g., film, book, music or even a Facebook post), suggest that media experiences may bring not only pleasure but also meaningful insights and inspiration. Furthermore, such experiences can reflect self-transcendence, resulting in focusing not only on oneself but feeling more connected to others or even inspired to make good-willing actions in the real world. One of the most powerful media in this context is music which has never been so easily accessible due to the technological progress, and, specifically, active music listening involves creative extramusical processes including emotions and visual imagery which vary depending on musical pieces, listeners’ musical perception and their socio-cultural environment. Therefore, listening to music may also evoke meaningful insights, inspirational states, and self-transcendent experiences; in fact, studies show that music is the no. 1 media source for seeking inspiration. This paper focuses on meaningfulness, self-transcendence, and inspiration from the perspective of music psychology and musical semiotics and presents the most recent empirical data on listeners’ perception and tendencies in Lithuania, also exploring the thin line between listeners’ personal (inner) and social (outer) experiences since individual extramusical associations are greatly influenced by the listener’s socio-cultural environment including other media.