Postcard assignments provide a concise alternative to the traditional analysis paper. In this article, I outline a series of four postcard assignments developed for an undergraduate post-tonal theory course, discuss connections to the Scholarship of Teaching and Learning (particularly to Self-Determination Theory), and examine student responses and pedagogical benefits. Synthesizing analysis and reflection, each postcard includes a 300- to 500-word essay as its message and a single page of annotated musical examples as its picture. Students analyze complete compositions through the lenses of specific themes; for example, students discuss pentatonic collections and pitch centricity in Debussy’s “La fille aux cheveux de lin” (Préludes, Book 1, No. 8). By addressing each postcard to a different recipient (peer, novice, expert, and future self), students learn to communicate effectively in diverse rhetorical contexts. Additional pedagogical benefits include greater independence in music analysis and increased confidence in writing about music.