This study examines the self-reported critical experiences that undergraduate pre-service teachers (PSTs) choose to share when writing a letter directly to "Math" and creating a self-portrait of a math learning experience. The letters sought to initiate a personification of math and the self-portraits to further explore math learning experiences of the PSTs. The letters and portraits were examined to understand the types of math relationships and critical events PSTs reported and their impact on PST identity and agency as a future teacher. Portraits were analyzed by PST research partners. The relationship between the categories of critical events and mindset was explored.