The unique challenges (and promises) teachers encounter today can be informed by the past. What literacy and language education mean for Mary Stewart, assistant professor of bilingual and English as a Second Language (ESL) education at Texas Woman's University, is a product of what it has meant for educators like her grandmother and mother. In this article, Stewart describes how her grandmother and mother's stories may provide relevant answers for the present and future. She explains how they inspire her to face challenges in the classroom by being passionate and being a learner. Herein, she shares three generations' stories of teaching English in Texas including accounts of what literacy education was like from the 1940s through the 1980s; the 1970s through the 2000s; and literacy education today.