This study aims to review the theoretical and empirical effects of working time reduction (WTR) and compare them with workers’ expectations and experiences. A survey was conducted with 61 individuals working 40 h per week, 36 workers who had undergone WTR, and 47 managers. The results showed that all participants were in favor of WTR; managers preferred reducing to a 4-day workweek, while workers opted for a flexible schedule. The expectations and experiences of WTR impacts on the society, economy, and environment were very positive, particularly in stress reduction, household responsibilities, and work–family balance. Experienced workers and managers recognized the positive economic effects of WTR on productivity and competitiveness, but other workers did not expect them. Contrary to the expectations of the other samples, experienced participants reported an increase in their consumption patterns, which needs to be considered, as the impact of WTR on the environment is mainly dependent on the workers’ activities. Understanding the effects of WTR and the support of workers and managers is crucial in decision-making processes.