Personal initiative training is a promising way to increase entrepreneurial personal initiative, which is a key behavior for successful entrepreneurship. Although personal initiative training has been shown to promote personal initiative, little is known about how this proactive behavior can be maintained over time and what the consequences are. The training transfer literature suggests that training effects usually decline with time. It is not clear, however, which factors contribute to personal initiative maintenance and which benefits go along with it. In a randomized controlled field experiment with 912 microentrepreneurs in Lomé, Togo, we investigate the influence of need for cognition—a cognitive factor driving proactive behavior—on personal initiative maintenance after training. In addition, we examine the effect of need for cognition on the well-being consequences of personal initiative maintenance. We show that people high in need for cognition tend to maintain posttraining personal initiative longer than those low in need for cognition. However, contrary to our predictions, need for cognition has no effect on the level of well-being that results from personal initiative maintenance. Our findings contribute to a better understanding of personal initiative and its maintenance and could be used to increase training effectiveness.