This unique thought experiment invites the field of agricultural education to a critical dialogue on issues related to making teaching a career. Leveraging elicitation techniques, we introduce a series of nine letters on agriculture teacher retention. Written by agriculture teacher education faculty with expertise in teacher retention, these letters orient readers to the collective thought experiment by introducing the complex reality of engaging in the field via multifaceted viewpoints representative of perspectives we have encountered within the profession. Representing the broad range of perspectives on teacher retention, readers can expect to initially agree with components of some letters and disagree with others; however, readers should refrain from dismissing perspectives as this opposes the need to collectively understand the depth and diversity of perspectives on teacher retention in agricultural education. Understanding these diverse perspectives is critical to creating innovative, adoptable solutions to address the explicit and implicit challenges and opportunities embedded within these letters. To support engagement in the thought experiment, we provided resources for reviewing the letters and contributing to the dialogue as appendices, with specific opportunities for individuals and groups to engage with intentionality. Readers are, therefore, encouraged to explore the appendices prior to reading the letters.