The rising of unknown contents from the depths of psyche such that lives are changed irreversibly, is a recurring motif shared by Jung’s psychology of the unconscious and Shakespeare’s dramatic works. Invariably shadow material takes possession, a loss of soul follows, when patience and long, painstaking work is required to find and recover what has been lost. This motif plays out repeatedly through Shakespeare’s plays, particularly the late Romances, developments that signal an evolving psyche, where lost soul is recovered, a resolution that didn’t happen in the earlier period. For both these men, the process of healing requires a descent leading to an encounter and acceptance of all aspects of one’s being. While this challenge was demanded in Shakespeare’s earlier period the obstacles proved insurmountable, and the inner division remained unresolved.