Quality of life is a multidimensional concept, a construct influenced by objective and subjective factors that include the evaluation of functional, physical, social, and emotional aspects of the person. The recent contributions of positive psychology present the quality of life as a fundamental indicator for health promotion and prevention strategies. In the recent psychological studies about this topic, courage demonstrated to positively affect several work behavioral outcomes, personal identity, and prosocial actions. Courage promotes change, innovation, and coping skills to achieve aims, and it correlates positively with many individual resources. The aim of the study was to investigate, according to the positive psychology approach, the relationships between psychological capital and two dimensions of quality of life—life satisfaction and flourishing—with particular attention to the mediation function performed by courage. The research was attended by a convenience sample of 807 Italian workers, balanced by gender, belonging to public, private, and non-profit organizations, and recruited on a voluntary basis. Participants responded to a structured online questionnaire containing the following measures: Psychological Capital Questionnaire, Courage Measure, Satisfaction with Life Scale, and Flourishing Scale. Cronbach’s alpha on each scale showed very good internal consistency. The collected data were analyzed according to a model of linear structural equations. In the first step, we conducted a confirmatory factor analysis (CFA) to test the model fit of the measurement model; in the second step, we verified the mediation hypothesis through Process v.3.1. Finally, the correlations were implemented using SPSS 20.0. The results showed that, in general, psychological capital predicts life satisfaction and flourishing, with an indirect mediation effect of courage only on flourishing. Two main conclusions emerged from the study: flourishing and life satisfaction are representative indicators of the quality of life; courage emerges as an important psychological resource that supports the individual to face and manage the uncertainties of the risk society.