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Teachers are acknowledged to play a vital role in our societies. Yet, for various reasons such as workload, job fulfilment and professional status, compensation, among others, there continues to be a global teacher shortage given low recruitment and high attrition rates. A large-scale representative survey of 4173 Singapore teachers across different career stages found teachers’ sense of fulfilment, enjoyment and pride (i.e., affective self-concept) to be the strongest correlate and predictor of retention intention. Informed by what we have learned about teacher-related variables to enhance teachers’ affective self-concept, this paper provides two possible paths to remedy, repair and improve teachers’ retention intention outcomes.