Although experts are valuable assets to organizations, they suffer from the curse of knowledge and cognitive entrenchment, which prevents them from being able to adapt to changing situational demands. In this study, I propose that experts' performance goal orientation resulting from pressures to perform contributes to their flexibility, but this mechanism can be moderated by learning goal orientation and humility. Data from a small sample of healthcare professionals suggested that performance goal orientation partially explained the mechanism of why experts may be inflexible. Humility, both as self-report and other-report measures, was found to be the most consistent moderator of this indirect effect. Experts with low levels of humility suffered from the negative effects of performance goal orientation, leading them to be less flexible compared to their counterparts with higher levels of humility. Experts who reported high levels of humility, on the other hand, were perceived to be more flexible as their expertise increased. Meanwhile, learning goal orientation partially moderated the indirect effect of expertise on flexibility through performance goal orientation. These findings lead to new conversations on how to get experts unstuck and highlight the importance of developing humility as both a personal virtue and a strategic advantage for organizations.