The problems of eminent creativity and its connection with clinical phenomena have long been in the focus of psychology and psychiatry research. A “madness and genius” narrative has existed for ages, but it became significant in the 19th century, and remained highly influential until today. Psychiatrists, representatives of the medical discourse, developed pathography as a method in the end of the 19th century in order to study how illness affects life-works and creative process. In the beginning of the 20th century Sigmund Freud formed another approach, psychobiography, which is not based on using different diagnostic categories; instead it is trying to unfold the interrelations between life history, psychodynamics and the creative process. In this recent article I will try to demonstrate the differences between the two approaches by concentrating on an outstanding Hungarian painter Tivadar Csontváry Kosztka, whose life history contains serious clinical aspects. Instead of following traditional clinical endeavors, in my approach I will take illness as a Jaspersian existential “boundary situation” that contributes the transformation of the whole personality. This transformational process does not lack progressive and regressive elements, and by analyzing its dynamics we can understand how creative activity—along with the feeling of evocation—can evolve and maintain the cohesion of the self by integrating traumatic emotional experiences.