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The author offers an account of his evolving relationship with the Rorschach test which for over 20 years as a private practice psychologist, he used in his clinical practice with the intent of mining patients' psyches for useful information about personality organization and functioning. Coinciding with having found himself on the homestretch of analytic training and during a time when he desired clarity on how Rorschach assessment and Jungian analysis could fruitfully merge, there was an unexpected shift in emphasis wherein the Rorschach suddenly became a method for looking at himself as well. This challenge to identify and integrate aspects of self hitherto neglected was found to enrich his clinical practice. An historical perspective on this experience is offered which highlights the enigmatic relationship that existed between Carl Jung and Hermann Rorschach. The proverbial question of ‘What might this be?’ has been asked when administering the Rorschach for nearly a century. From an analytic perspective, the question is more fully and meaningfully asked when the person doing the asking has also been willing to step in, look around, and take notice of what happens.