This article is an autoenthnographic account of the yearlong journey of two undergraduates and their instructor when the traditional classroom structures associated with the banking concept of education were altered in an upper division class and follow-on research experiences. These changes focused on foregrounding students' experiences of the uncertainties inherent in the process of coming to know. Scaffolding this process within a context of "healthy uncertainty" is described. Within this context, student engagement deepened allowing for generalization of knowledge and transformative personal experiences as the links between school and everyday life became more transparent.