Much research has focused on the reasons and mechanisms for immigrant language loss. However, there is a scarcity of research about influences on language maintenance over time, and much of this work employs survey data. With the current study, we aim to contribute to this body of research with a qualitative study of a bilingual individual, Esperanza Sada (a self-selected pseudonym), and her language and literacy development, beginning in late elementary school and concluding with a follow-up at age 22. We employed a language ideologies framework to interpret Esperanza's language and literacy practices, as well as the social, political, and educational contexts in which they developed. This long-term examination allowed us to understand more about the mechanisms and processes of Esperanza's language and literacy development and use over time. It also illuminated her deliberate choice to continue with bilingualism and biliteracy, even as some of her friends and acquaintances made the opposite decision.