<p>This theoretical analysis is a combination of the philosophical myth of Sisyphus, which is, in fact, the interpretation of the absurd provided by Albert Camus, and Self-Determination Theory (SDT), the PERMA model, and Psychological Capital (PsyCap). The research question is to learn the way leaders can manage the unending organizational pressures to maintain Positive Organizational Behavior (POB) and well-being of the employees operating within complicated work environments. The methodology of the study is conceptual, as it critically reviews the literature, which was determined using the academic databases of PubMed, Scopus, and Google Scholar. Mixed Methods Appraisal Tool (MMAT) was used to ensure the quality of methodology of the chosen primary research. The authors present the professors with the Sisyphus Struggle Theory, suggesting that organizational prosperity is the resultant product of constant struggle and fighting over the common cause instead of being challenge-free. By meeting the psychological needs of autonomy, competence and relatedness, organizations transform employees from being victims of the boulder to owners of the process. Leaders act as mythmakers and deploy emotional intelligence to redefine routine duties into stories of progress to attain a state of Sisyphus happy engagement. The theory transforms POB from a specific approach to solving a problem to a meta-theoretical approach to change as cyclical. It promotes strategic application of Positive Psychology Interventions (PPIs) like PsyCap training and work design that promotes flow to nurture grit and institutionalize perseverance as a key organizational virtue. Finally, the framework redefines work as a major source of human prosperity as opposed to a naturally burdensome process.</p>