Healthcare workers’ stress, burnout, and job dissatisfaction were exacerbated by the COVID-19 pandemic, whose mid-term negative effects are still present. The aim of this work was to consider the effects of burnout (psychophysical exhaustion, relational deterioration, and professional inefficacy) on the career satisfaction of healthcare workers. These relationships were evaluated by considering the direct and mediated effects of disillusion. For these purposes, the Link Burnout Questionnaire (LBQ) and the Career Satisfaction Scale (Occupational Stress Indicator—OSI) were administered to 295 healthcare professionals working at three Italian public hospitals in Cagliari, Italy. The analyses were conducted using the Partial Least Square Structural Equation Model (PLS-SEM) method. Outcomes highlighted that healthcare workers were in a condition of work distress, high risk of burnout, and career dissatisfaction. Also recognized was the direct negative effect of burnout dimensions on career satisfaction. Finally, the mediated negative effect of disillusion in the relationship between burnout and career satisfaction was identified. This study underlines the relevance of the dimension of disillusion, and its “bright side” fulfilment, in healthcare workers, specifically referring to the disregarded relationship between burnout and career satisfaction.