This chapter examines the two-sided nature of self-awareness and speculates why a cognitive ability that presumably evolved because it conveyed adaptive advantages is a primary cause of unhappiness and maladjustment. It draws upon theory and research in social, personality, evolutionary and clinical psychology. The chapter explores source of this self-reflection paradox and considers ways in which people may enhance their well-being by reducing the maladaptive aspects of self-awareness and cultivating beneficial ways of thinking about themselves. It discusses most of the behavioral problems that compromise human well-being, undermine the quality of life, and foster conflict among people would not arise if people did not have the ability to self-reflect. Indeed, many of the characteristics that are associated with hypo-egoicism—such as present-focused attention, experiential processing, and equanimity—are linked to psychological well-being and the quality of people's relationships. Thus, the first step in promoting a hypo-egoic orientation involves leading people to realize the myriad downsides of being excessively egoic.