This study helps advance the understanding of how school experiences relate to Latinx students’ college and career aspirations and self-perception. It used a longitudinal, narrative, multiple case studies design to document changes in nine students' academic, social, and identity pathways as they progressed from high school to college and what factors influenced that change. Results from this study determined that the dominant factor that influenced college decision in high school was financial realities. Background characteristics and experiences that influenced college transition and first year in college were AVID, emotional distress, and campus engagement. After their first year in college, students continued to envision themselves in successful careers and “making a difference” as they did in high school. The case studies further showed that the understanding of the steps needed to achieve their career goal and post-graduation aspirations generally varied according to the institution type they attended. Further, the challenges the students encountered during their first year in college were the amount of time dedicated to work and being unprepared for the new academic college culture, and the resources they utilized to help move them towards achieving their future goals were cultural brokers in and out of their school world. From these challenges and resources, the student narratives demonstrated they had developed a community-centered identity and high-achieving student identity even more by the end of their first year in college. This project has value in that it can help HSI practitioners, support and outreach programs, and administrators have a better understanding of how to serve their student population at the two-year and four-year college level to foster a thriving student population.