This study investigates how personality traits, specifically neuroticism and extraversion, influence retirement timing among older adults across Europe and Israel. Utilizing data from the Survey of Health, Ageing, and Retirement in Europe (SHARE), the research explores the psychological dimensions of retirement decisions, which are often overlooked in favor of economic and policy-driven factors. By integrating personality traits into the analysis, this study offers a more comprehensive understanding of what drives individuals to retire earlier or later. The findings reveal that neuroticism is associated with delayed retirement, likely due to heightened concerns over economic security, while extraversion correlates with earlier retirement as individuals seek social engagement and leisure outside of work. The study also examines the other three Big Five personality traits—agreeableness, conscientiousness, and openness—finding no significant impact on retirement timing. This cross-national analysis contributes to more nuanced retirement planning and policy development by acknowledging the diverse psychological profiles of retirees. The insights gained can inform targeted financial guidance and adaptive retirement policies that align with individual needs, enhancing economic stability and quality of life for older adults. The study underscores the importance of considering psychological traits alongside traditional factors in retirement research.