The main objective of this paper is to investigate the mediating role of subjective career success (SCS) in the relationship between proactive personality, social support (SS), and pre-retirement anxiety. Using a two-wave longitudinal design, 624 pre-retirees were sampled (M = 56.49 years; SD = 4.56); of these, 237 (37.98%) were males and 387 (62.02%) were females. Measurement model and mediation test were performed using the SmartPLS and IBM SPSS Amos software. The result indicated that proactive personality, SS, and SCS showed negative relationships with the dimensions of pre-retirement anxiety (financial preparedness, social obligation, and social alienation). Subjective career success mediated the relationship between proactive personality and pre-retirement anxiety.