Beginning with a brief historical overview of the oral tale, this chapter discusses its evolution to the literary tale and their differentiation. It then considers language and its relationship with the animate world as well as to magic and its power to enact wondrous transformation within the protagonist. The dominant structure of the oral tale is outlined along with a call for counter structures and themes. In support of the art of storytelling and its importance to the endeavour that maintains our humanity, this chapter frames suffering as a journey of necessity. This journey is highlighted as it unfolds through the particulars of the dominant plot, the heroic quest, and its counter plotline, a descent, or katabasis, to the underworld. Counter narratives about illness are less common today because they require different ways of doing and being, rather than the heroic those that seek to strengthen the ego. Through mythological and alchemical amplification, descent and its companion, nigredo, are viewed as the most negative, difficult, and dangerous of life’s unfolding movements. Read in its characteristic blackening, time spent in the icy underworld is described as a way toward transformation. Descent is also framed as a journey to the home of the dead, to the ancestors, and to the darkness of humanity – a depth that requires one to relinquish ego’s centrality in life, to sacrifice rational day-world expectations and preconceptions and to abandon hope. While less popular, this plot carries value, despite the hardships, because it teaches the primacy of the psyche, images, and the ancestors. It also reflects a fate that may have roots in transgenerational trauma. Here, the chapter makes a case for embracing the ways of the underworld, which has its own integrity and wisdom. In this journeying, suffering is seen as a way of knowing and a way of ethics.