Encouraging students to engage with principles and ideas is one way to address ambiguity with consistent, effective approaches in situations made up of "gray area." This includes the looming post-college world where students may be unsure about choosing between job offers, geographic locations, or even communication fields. Such ambiguity presents an opportunity to discuss academic concepts in new ways to help long-term retention while building life skills. Capstone courses, particularly those in advertising, public relations, and organizational communication, already offer such problem-based learning on a broad level, with group projects requiring a semester of higher-order thinking. The assignment discussed here, the "Approach Essay," helps students do the same individually. By getting students to apply principles to their post-graduation lives, the essay helps them manage uncertainty, work with and better understand academic concepts, and practice operating in imprecise circumstances. Addressing simultaneous needs for professional and personal development provides improved educational experiences mixing elements of both, inviting scholarship into their personal lives and personal lives into understanding scholarship (Zoffel, 2010). The objectives of this assignment are for students to create new connections among essential academic concepts and prepare for life post-graduation.