Writing, argued Lefevre (1986), Berlin (1988), Bizzell (1983) and others, is a social act. That is, writing is a tool for communication within specific contexts created by human interactions and is done to achieve purposes specific to the context. With this understanding, much of the research in writing studies that examines the social nature of writing focuses on the community in which writers write and the practices of those communities that shape texts (Bazerman, 1994; Devitt, 2004; Freedman & Medway, 1994; Miller, 1984). This research has provided important insights into the ways that texts are created, why they are created, and how they are created, and much of this research has been essential in shaping university writing instruction (Bizzell, 2002; Dias, et. al., 1999; Paré, 2002). . However, despite the important advances made in understanding the social context in writing, there has been little attention paid to individual human experience that shapes interactions between writers, readers, and texts. As Bakhtin (1986) explained, communication is not simply an experience of the moment. Rather, every attempt at communication is the culmination of a lifetime worth of interactions and experiences so that no individual can produce or respond to texts in the same way—student and teacher alike. Too often this human element is left out of undergraduate writing classrooms leaving students confused and frustrated with their writing experiences as they attempt to negotiate the unknown background of the professor grading their assignment. Thus, the purpose of this paper is to explore individual writing experiences within the context of higher education in order to lay bare the human element of writing and address fundamental concerns in university writing classrooms. In order to accomplish this end, this paper draws on a microcosm of academia in a five-year ethnographic study that explored the experience of learning to write within the Canadian Association for the Study of Language and Learning (CASLL)—a community that purposefully socializes writing and uses it to collectively generate knowledge through a freewriting activity called inkshedding. CASLL represents a microcosm of academia in the way that participants join a specific disciplinary conversation, learn to take a position, undergo review and face the pressure of writing something that will resonate with readers. Experiences in this community expose hidden agendas of power and equality and the challenges for individual learning experiences. Understanding the human impact of these hidden agendas provides insights into the ways undergraduate students struggle to produce acceptable texts for their classes and may have implications for enhancing their experiences learning to write in the academy.