To elucidate how and why hotel employees proactively engage in career development, this study explains the indirect effect of future work self (FWS) on their proactive career behavior through career engagement. Drawing on conservation of resources theory, this study discusses the moderating role of organizational support for development (OSD) to highlight why OSD is important for those who have low-level FWS. Results of the 205 hotel supervisor–staff-matched data show that career engagement mediates the relationship between FWS and proactive career behavior. Furthermore, OSD can be considered a compensatory moderator that determines the indirect effect of FWS on proactive career behavior. This study provides further theoretical and practical implications.