Information and communication technologies are so embedded in modern society that we have arrived at the point at which learning to use technology successfully may affect our day to day lives as much as does learning to eat or exercise properly. While information systems scholars have studied interesting post-adoption constructs such as continuance intentions and IT-appropriation, research explaining and predicting successful system-use (i.e., system-use that adds value) has been scarce. A better understanding of successful system-use would benefit both research and practice – scholars’ knowledge of positive outcomes of human-computer interactions would expand and practitioners could gain insights toward improving employee added-value system-use. We pursue this study by theorizing around user characteristics, adaptive behaviors, and system-use outcomes. Our findings suggest that it is not only who you are, but what you do, that drives successful system-use.