Based on proactivity literature, feedback seeking behavior is generally used throughout an individual’s career to enable better adaptation to the work environment. However, it has recently been shown that declining levels of feedback seeking behavior may result in decreased psychological attachment over time. This study aims to explore whether individual adaptivity represents a mechanism through which feed-back seeking affects psychological attachment (i.e., well-being involvement and withdrawal). In addition, the interaction effect of organizational obstruction between individual adaptivity and psychological attachment was examined. Based on three-wave survey data obtained from 273 participants from French organizations, a moderated mediation model was tested using structural equation modeling. Results confirmed that adaptive performance mediated positively the relationship between feedback-seeking and well-being involvement and negatively with withdrawal. Moreover, perceived organizational obstruction moderated negatively the relationship between adaptive performance and withdrawal, and positively that with well-being. These results shed new light on the relationship between proactivity (i.e., feedback seeking behavior) and adaptive performance, but also on the positive short-term contribution of successful adaptation in a perceived obstructive organizational context. Theoretical contributions and practical implications for human resource management are discussed.