Information and communication technologies are so embedded in contemporary 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 learning to eat or exercising properly. However, we lack research that explains and predicts successful system use (i.e., system use that adds value to the user). We theorize that adaptive behaviors (e.g., trying new features, repurposing features) mediate the relationship between user characteristics and successful system use. To better understand successful system use, we used an online survey to study how undergraduate students enrolled in an information systems course used an information system (Microsoft Excel). Our findings suggest that adaptive behaviors do act as a mediator between user characteristics and successful system use; therefore, it is not only one’s identity but also what one does that drives successful system use. One of our key contributions includes remodeling system success as a single second-order construct as opposed to its traditional form as a series of causally related constructs.