Weber’s thesis of the disenchantment of the world is interpreted as “we-prison” in Dialogical Self Theory (DST). As a counter-example, the phenomenon of awe is presented as an experience that opens the self to the wider universe. In that context, Martin Buber’s work on spirituality and Rollo May’s work on creativity are compared. The shadow sides of mystical experiences are outlined and compared with psychotic states of the mind. The work of Aldous Huxley who described the workings of mescaline as a facilitator of mystical insight is presented. Mystical experiences change the so-called “minimal self” on a more basic sensorial level, and they differ from the narrating and the positioning self. Furthermore, Donald Crosby’s “perspectivism” is incorporated in DST under the heading of “positionalism.” As a practical implication, specific guidelines are presented in order to open the self to the experience of awe as a first step to the “depositioning” of the self.