By use of a case study, this paper interprets the phenomenon of a “self-affliction tendency,” based on the theory of self-disorder (Wu, Lin, & Lu, 2016). According to definitions taken from Kohut’s theory of self-psychology, there are four dimensions of self-affliction: existential alienation, dysfunction, poor self-care, and contradictory relationship within the framework of self-disorder. The obvious behaviors of self-defect can be found through self-observation. Using this framework, the analysis focuses on the case study of Jack, who was living with depressing life attitudes and was lonely and spiritually dead, all because of poor development of the inner-self. Jack also encountered the experiences of addiction, emotional alienation, and other interpersonal difficulties. As such, his situation was consistent with the definitions of “self-disorder” and “self-affliction tendency.” The paper concludes that seeking understanding of the four dimensions of self-affliction could be potentially helpful for practitioners in realizing the nature of self-defeating and self-destructive behaviors. In this sense, it might also be able to help prevent or address physical and mental illnesses in people’s lives.