The 21st Century American workforce will include a larger proportion of older workers, as well as other demographic groups currently under-represented in the IT workforce. Surprisingly, some older IT professionals report problems landing a job in an era when government and private organizations are proclaiming a shortage of IT workers. Apparently, there’s a disconnect between the skill sets of these experienced professionals and the skills being sought by contemporary organizations. This study provides a preliminary view regarding the updating efforts of IT professionals by age category, and then elaborates by examining self-reported professional competency motivation and perceived organizational outcomes commonly associated with demonstrated professional abilities. Overall, the study finds that older IT professionals participate less in formal updating activities, and perceive less value in maintaining professional competency. Decreased competency motivation may be related to pessimism regarding the probability of receiving organizational rewards when professional ability is maintained.