Supporting college and career readiness among youth who encounter significant academic and life challenges requires innovative strategies to help them envision their futures, leverage their strengths and develop dispositions that promote positive trajectories. For youth development professionals who develop and implement novel programmatic approaches to support the college and career readiness of underserved youth, it is critical to acquire a deeper evidence-based understanding of factors shaping positive career and college pathways as well as to incorporate stakeholder viewpoints in their program design and delivery. In this article, we share key insights from our program development process that can inform the work of program developers, educators and youth services providers who seek to build and enhance career- and college-readiness programs aimed at underserved youth. We summarize 4 key insights from a narrative review of literature on college and career readiness as well as findings from a set of stakeholder (student, parent and educator) focus groups. We offer our ideas for incorporating these insights alongside stakeholder input into the development and design of college and career readiness activities and programming.