The current study integrates ideas from the successful aging at work paradigm with theory and research on retirement motivation with a sample of midlife workers (Nﾠ= 397; Mageﾠ= 52.34; SD = 5.87) over a 16 month period. We conceptualized successful motivational aging at work as a typology of successful, usual, and unsuccessful motivational aging at work and provide empirical support for the validity of this typology. Motivation to work was defined as retirement age and post-retirement work intentions. We found that promotion-focused trait orientation and personﾖjob fit were predictive of successful aging classification and that work centrality and retirement-related attitudes were related to motivation to work outcomes. Successful aging at work classification, however, did not predict motivation to work outcomes, operationalized as intended retirement age and post-retirement work intentions. Our findings provide support for the dynamic process of motivational aging at work and provide evidence that trait and contextual variables can predict this process. Furthermore, we show that retirement decisions are complex and influenced by an array of work and nonwork attitudes.