Computer Science classes teach skills, topics and knowledge areas – often without context where they will be used in future classes. Throughout time, students constantly struggle and ask questions like “Why am I learning this?” and “What value does it hold?”. In addition to not seeing the correlation on topics, students fail to see what benefits this could lead to in the future. First generation students and those without connections to the computing industry are at a distinct disadvantage in connecting the dots between the courses they take, the skills they can learn and possible careers. When asked what they see themselves doing in the future, nearly every CS student responds, “software developer”.[6] In this paper, we discuss a project that we are working on called Pathways. Students can easily see all of the CS courses. They then choose a course of interest and immediately see the prerequisites and paths to courses that open because of this selection. There is other data that is displayed including topics covered, skills learned and careers that open with those skills and more. The overall goal is to help retain students in CS program and increase their satisfaction with that decision.