A mobile and boundaryless career generates learned helplessness especially when employees faced with frequent failures in their career. However, the notion of career crafting proposed by recent scholars provides a way to alleviate this negative state. Based on conservation of resources theory, we aim to explore when and how career crafting reduces learned helplessness. We conducted a two-wave study and collected data from 306 employees in China. The results indicate that career crafting is negatively related to learned helplessness. In addition, resilience plays a mediating role in this process. As a boundary condition, gender moderates the impact of career crafting on resilience, and female respondents are more able to improve their resilience through career crafting. We expanded the literature on career crafting and resilience to interact with the career literature based on conservation of resources theory. Our study thus highlights the importance of career crafting and its implications for reducing learned helplessness, especially for women.