This episode explores the evolving concept of self-esteem and its relationship to societal trends, particularly the perceived rise of a "victimhood pandemic." Against the backdrop of the COVID-19 pandemic, the conversation delves into the shift in cultural attitudes towards victimhood, contrasting past emphasis on overcoming adversity with a current focus on competing for victim status. More significantly, the discussion analyzes the psychological underpinnings of this phenomenon, introducing the "victimhood Olympics" and the concept of "moral typecasting," where being perceived as a victim grants perceived moral superiority. For instance, the hosts discuss how college essays have shifted from showcasing resilience to emphasizing hardship. As the discussion pivots to the nature of self-esteem, the guests introduce a modified Maslow's hierarchy, emphasizing the importance of basic needs like connection and safety alongside higher aspirations. In contrast to a purely achievement-based self-esteem, the hosts advocate for a more intrinsic sense of worthiness, independent of external validation. This leads to a discussion of the dark triad (Machiavellianism, narcissism, psychopathy) and its prevalence in leadership, contrasted with a proposed "light triad" of prosocial traits. Finally, the conversation touches upon the potential impact of advanced AI on human work and the subsequent re-evaluation of self-worth, suggesting a potential shift towards prioritizing relational value over instrumental value.