We tested a predictive model based on self-determination theory (SDT) to demonstrate how job design choices contribute to subjective career success. Data collected at Time 1 demonstrated that the job characteristics of autonomy support and competence support had direct and interactive effects on employees’ need satisfaction. Need satisfaction at Time 1 mediated the relationship between autonomy support and self-determined work motivation at Time 2. Work motivation, in turn, mediated the relationships between need fulfillment and career attitudes that characterize subjective career success. These findings are theoretically important because they demonstrate that SDT can bridge job design theory and career theory, pointing to new ways that job and career experiences are interrelated. From a practical standpoint, the results are valuable because they show that job enrichment efforts guided by SDT have important implications for promoting career success perceptions and vocational retention among experienced workers.