When I began this journey two years ago, I was looking for answers to a question that had become increasingly pervasive and yet frustratingly intangible in my teaching practice: how could I resolve the student I was with the students I now teach? Despite my exposure to some new ways of thinking about teaching and learning and my development of some powerful professionally collaborative relationships, there was still a disconnect. I was ready to do something about that. While my coursework an d readings offered many “lenses” of reflection on this disconnect, it was when I began to inquire into Wiggins’ and McTighe’s (2005) framework of backward design that I began to see a way to actually resolve the disconnect within myself and with my student s. Wiggins and McTighe propose a distinction between knowing and understanding, asserting that “ an understanding is the successful result of trying to understand – the resultant grasp of an unobvious idea, an inference that makes meaning of many discrete ( and perhaps seemingly insignificant) elements of knowledge ;” in my teaching journey these past two years, I have endeavoured to understand how to make meaning out of the knowledge, experiences , and assumptions I brought with me to my program, and my inferences have shifted every aspect of what, how, and why I do what I do in the classroom closer to closing that gap between myself and my students. In this reflective paper, I will employ Wiggins’ and McTighe’s framework of backward design as a means of charti ng my movement from knowing to understanding , for while I began this program with an end in mind, I realize I also now end with a new beginning in mind.