Many students attend college to prepare for stable careers and pursue social mobility, especially first-generation (first-gen) students who often become "boundary crossers"—navigating unfamiliar social, economic, and professional landscapes. While much has been written about their educational experiences, less is known about their career development and the challenges they face transitioning into the workforce. This brief addresses that gap, using survey and focus group data to explore how first-gen students manage the unique, complex process of career exploration and entry, highlighting both the institutional support available and the often-overlooked socioemotional and cultural aspects of boundary-crossing.