<p>In the early 21st century environmental, social and cultural changes are confronting the traditional relationship one has with technology, space and subsequently architecture. More specifically the tools of design are becoming integrated, whereby the clarity of tradition is becoming overlapped, becoming blurred. With this in mind the research investigates the opportunities of an iterative hand drawing process to develop architectural responses to movement, time and transformation. Highlighting a future which is inevitably changing, it is important to assess the inherent qualities of our design tools, as they too influence the connection and formation of architectural space. The research explores hand drawing through a design process which firstly, challenges drawn representation techniques and secondly, emphasises movement and transformation as key architectural drivers within the 21st century. Due to the continual developments within technology, construction practices and design materials, there is an opportunity to question and reflect our changing built environment and hence, the role of movement in architecture. With reference to the theorists Catherine Ingraham and Robin Evans, the research develops the position that the practice of architecture has become restricted by linear ordering systems. This is reflective in the orthographic representation of architecture alongside the built edges and boundaries of architectural spaces. Therefore, today's transforming conditions are used to validate and further articulate Ingraham's and Evans's theories, outlining a design response, using Wellington as a case study, built upon overlaying environmental, social and cultural relationships. The architectural outcome connects rather than dissociates itself to transforming conditions, creating multiple rather than singular boundary conditions through architectural blurring. Traditional relationships to spatial boundaries and edges are critiqued through the ambiguities and layers of working within an iterative hand drawing process. The influence of hand drawn qualities has provided a way to insert motion into a construct which is perceptually static, hence introducing a means to negotiate and work within a period of transition.</p>