This paper is an analysis of the challenges of dealing with the human and technical aspects of blended learning. It presents a case study of how one course has evolved over the years, presenting not only the lessons learned and the changes made at each stage, but the rationale for those changes. Looking at learning as the combination of information and interaction, the paper describes how the instructor went from being the Sage on the Stage to being the Sage in the Cage, to being the Guide on the Slide to finally being the Guide on the Side. It also documents how the course went from being technology driven to learner driven, and the evolution of an activity cycle. The paper ends with rationale for design changes and implications for current and future designs.