Jung's concept of the shadow is explored in this paper through his writings on its realization and assimilation in which he says the shadow may be experienced as the regressed and denied ‘other self’ in each individual. However, this is not the whole picture, and he also points to the fact that the shadow contains more than something merely negative. While in no way treating them as ‘patients’, the paper will also touch on the experience of the anthropologist, Bronislaw Malinowski, and the writer, Joseph Conrad, in their personal encounters with the shadow. All three encountered the shadow whilst going through rites of passage of their own and each owes much to the Romantic Movement. In this context, attention is directed to the writings of the philosopher and theologian, Johann Gottfried von Herder, who discovered a deeper understanding of his destiny in the course of a sea voyage.