For emergent bilingual students in U.S. schools, narrow emphasis on monolingual-like language proficiency and deficit-oriented practices such as academic tracking continue to limit their educational opportunities. Informed by robust views of bilingualism as a borderlands in between linguistic and cultural practices, this dissertation study explores how Spanish-English bilingual youth leveraged a critical awareness or mestiza consciousness (Anzaldúa, 1987) to navigate their schooling trajectories by enacting their sociocritical literacy to design paths to college (Gutiérrez, 2008). The study took place in a midsize Midwestern community with six bilingual Latinx youth in their first year of college. Ethnographic methods including interviews, artifacts of bilingualism, and written reflections highlighted how youth navigated their schooling trajectories and the role their languages played in these experiences. Findings show that when youth's bilingualism is understood in relation to cultural-historical contexts, power relations, and intersecting identities, the mestiza consciousness it can foster serves as a resource for identity work on the path to college. The first analysis chapter explores how bilingual youth enacted and embodied mestiza consciousness while designing their schooling trajectories. The second chapter focuses on the role of bilingualism in mestiza consciousness as youth leveraged a hybrid perspective to navigate the divergent values attributed to their bilingualism in school spaces. The third chapter analyzes how youth organized resources from family, school, and community networks of support to enhance their schooling experiences, access postsecondary opportunities, and become designers of new social futures. These findings illuminate bilingual youth's borderlands identity work, understood as the way youth navigate their schooling trajectories to strategically position themselves for future success. This research demonstrates the importance of bilingual youth's critical awareness to read situational power dynamics, balance multiple roles, and construct empowering personal narratives for specific audiences. These strategies helped bilingual Latinx youth, who are historically underrepresented at postsecondary institutions, to prepare successful college applications, manage family responsibilities, meet academic expectations, and maintain asset-based views of bilingualism in the face of marginalizing discourses. This research expands ideas of language proficiency to support responsive and sustaining pedagogies for diverse students, highlighting the role of bilingualism in issues of equity and college access.