In this article I will describe and illustrate how personal crises of patient and analyst, in contrast to the more commonly recognized detrimental effect, can actually facilitate a mutually transformative process. While I was in the throes of my own personal crisis, a very challenging patient arrived for treatment. How that analysis evolved over the course of 12 years to become a mutually transformative and creative process for both the patient and myself is the focus of this article. To augment delineation of this process, I will use St. Exupery’s The Little Prince as a literary depiction of what I believe to be the essential healing elements involved, poignantly illustrated with excerpts from the book.