This study is interested in understanding the phenomenon of authenticity from an empirical perspective. It examines what is it like to experience an authentic being and the transition from an inauthentic life to an authentic life sequel to a significant life event. This research is interested in understanding the manifestations of the phenomenon of authenticity in the significant experiences of its participants. Discussions on authenticity have often implicated moral or ethical questions. This study explores this phenomenon by posing a moral question to the participants, which may easily resonate with their significant experiences and may elicit the desired responses on the phenomenon. Participants were sampled from among university students and older adults in the American South. In all, 123 participants were sampled. Participants were asked to describe, in as much possible detail, an event in which they did something morally right which provided a significant sense of fulfillment, and/or something morally wrong that they did that brought them the greatest regrets, respectively, and how the experience transformed their life. The participants’ significant experiences (protocols) were collected and analyzed using the Descriptive Phenomenological Method in Psychology (DPMP). The results have shown various manifestations of the phenomenon of authenticity, the meaningful psychological structure of authenticity, and the inherent six dimensions of authenticity that explain the psychological process.