Employees are increasingly given control over how they learn, and their choices for training are diverse and varied, yet employees must balance competing demands. On one hand, they are expected to be increasingly efficient in their current job duties – on the other hand, they are expected to develop new skills and competencies that enable them to adapt and respond to changing job demands. Drawing from the organizational learning literature, we propose a model of worker and work characteristics that inform choices between two mindsets related to learning at work. The first mindset is exploration, or the pursuit of learning outside one’s current knowledge domain; the second mindset is exploitation, the refinement/deepening of one’s existing knowledge stock focusing on the task at hand. We further propose that these strategic choices, or trade-offs, influence employee learning and performance in unique ways, with different implications for both routine and adaptive performance. Finally, we incorporate the notions of feedback loops and risk assessments that influence ongoing decisions between exploration and exploitation mindsets. Recommendations for future research and extensions of the theoretical model are also proposed.