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This study is based on twelve months of ethnographic data collection where the main goal was to examine Latino/a students’ transitions from high school to college. This proposal, specifically, draws on anthropological theories of identity to examine the role of parents and siblings in shaping Latino/as youth’s aspirations to become the first in their families to pursue postsecondary education. Findings suggest that family members held high expectations for participants to attend college and become role models for younger siblings. Participants were proud to become role models; however, they experienced tensions in negotiating identities. As participants themselves did not have role models for higher education in their families, they feared the possibility of disappointing their parents and siblings.