In this paper, I discuss the process of redesigning and teaching a mandatory, academic skill building course for students on academic probation at Mount Saint Vincent University (MSVU) in Atlantic Canada. The rationale for redesigning the course was to offer an alternative curricular framework, including instructional approaches, to course instructors who taught a modular-based curriculum. The original course was designed to focus on improving students' individual self-efficacy and motivation for academic success; however, the social and relational nature of learning was not articulated as an underpinning theory in the curriculum. In the new curriculum, I draw on both Etienne Wenger's (1998) notion of communities of practice as sites for learning and Howe and Strauss' (2000; 2007) work on generational analysis as theoretical frameworks. Furthermore, I incorporate Wenger, McDermott, and Snyder's (2002) design principles for cultivating communities of practice as a framework for translating theory into practice. The initial information that I collected from students, instructors, and a thorough review of the original curriculum led to the main inquiry question: How can a curriculum, centred on building community in the classroom, help students to cultivate meaningful learning experiences that take learning beyond a "fake it 'til you make it" mentality? This question guided the curricular design process and also my experiences teaching the course at MSVU during the Fall semester of 2012.