The dread and resistance which every natural human being experiences when it comes to delving too deeply into him or herself is, at bottom, the fear of the journey to Hades. There is a pervasive malady in the air. Terrorist attacks, violent social upheavals, species extinctions and natural catastrophes like tsunamis leave human with an uncanny sense of menace. Although climate change, financial inequality, dependence on fossil fuels, migration, the loss of species and biodiversity are all pressing problems requiring political agency to correct, they are symptoms of the greater cultural malaise, a deep sense as a species, humans have made a wrong turning and lost the way. This chapter presents the need for cultural transformation involving relinquishing human privileged superior status as a species, which has had such destructive consequences for the other-than-human and shared planet. The challenge of this relinquishment is a scary descent through a borderland reality along the lines Jung called for almost 90 years ago.