This article aims to examine the motive of the underworld journey in the poetry of Oliver and Whyte. This examination reveals the idea that we can only uncover the secrets of our souls by journeying into the unknown, deep into the darkness of ourselves. In contemporary industrial society, no one is willing to enter the underworld except when carried off, like Eurydice or Persephone, by a great loss, or by depression. Yet our individual soul is the core of our human nature, the reason for which we were born, and the essence of his specific life purpose, and journeying into the underworld is a way of meeting our soul`s desire for a more fulfilling life. What the soul longs for may have little to do with any of our ego`s schemes―for abundance, for peace, for release from struggle and conflict; the soul is truly eager for a larger life. This will seldom be found in avoidance, but in seeking places of spiritual risk and psychic danger. The goal of life is not happiness but meaning, and therefore those who seek happiness by trying to avoid suffering will find life increasingly superficial. For Oliver and Whyte, life is not a problem to be solved, finally, but a series of engagements with the cosmos in which one is asked to live as fully as one can. Their poems seem to suggest that in so doing we serve the transcendent meaning that is expected to be brought into being through us.