In this article, we draw from an in-depth interview sequence to story how a Latina’s delayed professional trajectory into the New South schoolhouse was, in large part, due to her mother’s warning that K-12 teaching was a dead-end career for losers. Our analysis underscores the emotional tensions that Janet Castillo (a pseudonym) navigated as she struggled to reconcile the burden of her mother’s approval with her own professional dreams. We suggest that even as contemporary research has voiced Latinas’ multi-layered resistance to their essentialization as subaltern women in oppressive educational and professional spaces, more nuanced inquiry is needed to understand the profound influence that Latina mothers exert on their daughters’ choices to (not) teach. We conclude with recommendations for research and praxis surrounding the dynamics of families in growing the Latinx teacher pipeline.