In this paper I focus on two Spanish translations of Gloria Anzaldua's classic, Borderlands/La Frontera: The New Mestiza. First published in 1987, Borderlands had been translated into Italian by Paola Zaccharia, but it was not until 2015 that my translation to Spanish was published in Mexico by the Programa Universitario de Estudios de Genero at the Universidad Autónoma de Mexico, and in 2016 Carmen Valle Simón published her translation into Castilian in Madrid. Through a testimonio format, I will speak about the position of the translator who resides in both the original and the target languages. Bringing to the forefront issues of race, class, and geography, I work through some of the thorny issues that arise in doing a translation of a complex text such as Borderlands from what could be called an insider position. If as most translation theory holds “The choices made by the translator during the process of translation are an essential part of producing an adequate target text,” then the bilingual translator who also accesses a culturally centered language may have to make other choices as well. I submit that when the variants of a language are also situated at the crossroads of cultural and historical territories the translator's complicated negotiations in making these choices must go beyond the linguistic choices to the culturally and socially situated choices. By looking at a section of prose and at a poem, the choices reveal the translators' subject position and what factors impelled certain choices.