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Teachers have a powerful impact on student achievement, yet high attrition rates hinder schools in their ability to provide quality instruction. While many studies have examined factors related to attrition, including salary and administrative support, and others have explored the emotions of teaching, studies have not investigated the emotions of leaving teaching and the impact of these emotions on the decision to leave early. This study closely examines the emotional experiences that come with leaving teaching early (within the first 5 years) using qualitative interviews to capture the perspectives of 25 early leavers (15 former public and 10 former Catholic school teachers). Findings revealed that leaving teaching was more than a pragmatic decision where participants weighed the pros and cons of staying in the profession; instead, the decision led to negative and positive emotions that continued to change as these former teachers processed their experiences and decision.