The psychological implication of retirement is underemphasised. This study examined the relationship between proactive personality, social comparison, and retirement anxiety among Nigerian civil servants. The study is a cross-sectional design, using proactive personality, social comparison orientation, and Nigerian pre-retirement anxiety scales. Five hundred and eight staff members in government-owned tertiary institutions with five years or less to go until retirement, and at a mean age of 57.47 (SD = 3.02), were surveyed. The study established that a proactive personality negatively predicted retirement anxiety and that civil servants engage in diverse forms of intrapreneurship/entrepreneurship to augment their savings. The study also revealed that social comparison (opinion) mediated the relationship between proactive personality and retirement anxiety (financial preparedness and social alienation). In addition, the study found that social comparison (opinion and ability) mediated the relationship between proactive personality and retirement anxiety (financial preparedness) in a sequential order. The findings suggest that retirees in Nigeria face complex challenges, including financial unpreparedness, social alienation, and uncertainty. The study highlights the importance of understanding the relationship between personality traits, social comparison, and retirement anxiety in order to develop effective interventions and policies that support retirees in Nigeria.