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Gritty optimism is the belief that students can do more than they thought possible through productive struggle that leads to joy. The purpose of this paper is to answer the following research question: How does gritty optimism affect school leadership for thriving learning communities? Over the past decade, we have collected survey (n = 9,535), interview (n = 342), and focus group data (n = 427), of Pre-K-12 teachers and administrators across the United States and Canada. We have also conducted numerous school site visits (n = 56). We have identified five primary findings from this research that provide insights into how gritty optimism fuels collective leadership, collective efficacy, and school improvement.