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This article reports on a longitudinal project that attempts to situate student writing in the space between the worlds of academia and workplace. The project was conducted by several groups of students who took the same course in different years. The authors argue that student engagement in knowledge sharing with a workplace discourse community allows students to experi-ence the workplace context from within, adapt their academic knowledge to it, and apply this knowledge appropriately. Such longitudinal projects pro-vide students with an opportunity to enter into a productive dialogue with previous generations of students and build upon their work. Projects designed to ensure knowledge sharing and collaboration promise to help students bet-ter understand the intricacies of workplace communication and find connec-tions between academic knowledge and workplace practice.