Adventure is a playful pacemaker for real border crossings from reality to possibility; it can, from a benevolent point of view, be the trigger for individual changes of reality, a provider of impulses for the development of self. Confronted with the unpredictability of the wilderness, the turbulences of torrents, the chaotic state of the oceans, the pathless expanse of the forests, the adventurer must be prepared to encounter such surprises, but he can never be sure when, where and in what form they will occur. In this article, the author explains how the "what would happen if" thinking develops among adventurers. He discusses how the "coniunctivus potentialis", as an expression of the power of imagination, can be a productive source of possible realities, which the adventurer might encounter and which he will have to react to. He also describes that adventure can be of interest to the field of youth social work and youth support. Adventure does not only meets the child's curious urge to explore the as yet unknown world, it also promises everything the pedagogics of the age of philanthropism once feared and what many school teachers still fear today: surprises, disruption of routine, and activation of the sense of possibility, which can complement reality and can change it.