In this article, three educators 12 years into their careers discuss what they've learned about teaching. The educators, all of whom attended the same undergraduate institution and completed their student teaching together, begin by reflecting on their training experience and how it prepared them (or didn't) to face the daily challenges of the classroom. The conversation turns to significant failures, proudest moments, and the vital role creativity plays in teacher longevity before settling on reasons these educators keep teaching despite the fact that more and more people are leaving the profession or avoiding it altogether. By the conversation's end, a message of hope emerges, one that identifies imagination and community as fundamental to a teacher's long-term success.