The lives and experiences of students, families, faculty and professional staff who identify as first-generation are the subject of increased attention in higher education across the United States. The success of programs, initiatives, and interventions mostly focus on measurable student “outcomes” but may often miss the complicated narratives of aspiration, sacrifice, accomplishment and identity work first-generation students, families, faculty, staff and communities navigate. Portraiture can make visible the triumphs and challenges of being first in the family in higher educational spaces.