Thriving is a great indication that an individual manifests enthusiasm, effective knowledge acquisition, job satisfaction, and commitment. This study was conducted to explore the personal and contextual enablers that serve as predictors of the participantsâ€™ thriving at work. This study utilized a descriptive-correlational research design to gather quantifiable information on the relationships between the variables. The participants of this study were the ninety-five (95) DepEd library employees of Agusan del Norte and Butuan City, selected through simple random sampling. The descriptive-correlational design was used in this study, and a researcher-made questionnaire was utilized as the tool for data gathering. The following findings were revealed: personal and contextual enablers were rated at a very high extent by the participants; the participants had a very high extent of vitality to indicate their thriving at work. In terms of the learning dimension of their thriving at work, the participants rated it to a very high extent; and based on the regression analyses, the strong predictor of the participantsâ€™ thriving at work, specifically on its learning dimension, is the challenging environment. As to the vitality dimension of thriving, the identified strong predictors are piety and religiousness, affection and trust, and a challenging environment. Thus, the enablers predict the participantsâ€™ thriving at work. It is recommended that their employer provide opportunities that will consistently uphold the enablers that will facilitate their employersâ€™ thriving at work.