Risk taking behavior can be both adaptive and maladaptive depending on context. The majority of studies of risk taking, however, focus on clinical populations and dangerous or harmful risk taking. Individual differences in learning during risk taking are rarely examined in relation to task performance. The present study examined risk taking and associated outcomes in an exploration-based instrumental learning task (Balloon Emotional Learning Task; BELT), which presented a series of balloons in which participants pump up for points. Consistent with prior work, sensation seeking predicted increased risk taking behavior. Importantly, however, a significant interaction between sensation seeking and associative sensitivity, an attentional construct defined as the frequency and remoteness of automatic cognitive activity, was found. Specifically, among individuals high in sensation seeking, associative sensitivity predicted fewer balloon explosions and an increase in points earned on the balloon condition with the most potential feedback driven learning. Thus, these findings suggest that sensation seekers are a heterogeneous group, and secondary traits such as associative sensitivity moderate behavior such as risk taking and learning according to context.