This study investigated the similarity of the factor structure for self-reported versus supervisor-rated employability for two age groups of workers, and then validated a career success enhancing model of employability across the two age groups. The results confirmed a two-factor model including self-reported and supervisor-rated employability as underlying factors. Moreover, Multi-Group Structural Equation Modeling (SEM) indicated that for the youngsters both self- and supervisor ratings of employability related significantly to objective career success outcomes. However, for the over-forties self-rated employability related positively to promotions throughout the career, while the supervisor ratings related negatively to overall promotions. The findings have important implications for performance appraisal practices aimed at increasing life-long employability and career success.