Despite the growing research about depersonalization, depersonalization continues to be a neglected phenomenon that is easily pathologized, simplistically reduced, commonly misdiagnosed, and misunderstood. Using a hermeneutic and heuristic approach, this thesis shows depersonalization a new curiosity that this writer feels has not yet been shown. Through a phenomenological, depth psychological, and imaginal lens, this thesis explores the duality of lightness and heaviness, imagination, and soul as related to depersonalization. A fictional account of depersonalization is given to deepen insight into the topic. Lastly, this thesis connects depersonalization to the idea of the unbearable lightness of being and explores how this framework has wide implications and possible contributions to psychotherapy.