Adopting an empirical teaching/working experience against an urban design theory backdrop, this paper investigates ‘Design Thinking’ from a personal view. It explores the interplay between the different design disciplines and offers an interpretation on how the lines between them blur and how they may connect(ED) through teaching programs. A brief history of urban design introduces the subject, demonstrates the dynamic forces of the city, touches on the ongoing tussle for definition of Urban Design and ultimate recognition of it’s distinction from Architecture, Planning & Landscape Architecture as an independent profession. Once the lines are drawn, it is time to move on and acknowledge the indispensable value of crossing the lines & connecting design fields, a function that recognises; ‘…that designing is a multi-layered thing, to be learned slowly, layer by layer, but designers must combine all the layers at once, and understand their interaction…’ (Venturi2004) It is this layering that requires a learning experience and the input of a ‘thousand designers’ in order to create rich and meaningful built environments. With the advent of information technology the design process has been accelerated and the sharp lines of separation between the design disciplines are blurring. A powerful common visual tool has been created that encourages a cross communication of design ideas and broadens the scope for discovery, invention and connection. The educational imperative is determined through a program aimed at a holistic approach to urban design, available to students across the design disciplines in the Faculty of the Built Environment. The philosophy is based on communicating new visual insights, through an interactive participation program that draws on the valuable contribution of personal experiences of students on the course. The program, as a Seminar offers an appreciation of the complexity of the subject through understanding the parts; as in-situ investigations, readings, discussion, drawing, debate & presentation. The focus is the fascination of urban design interventions in the 21st Century and the propensity for rapid change as part of the dynamic process of cities. Intrinsic to the program are primary links to Planning, Architecture and Landscape Architecture in addition to diverse design associated activities. ‘…the new millennium will depend on the creation of bridges that unite conservation technology with an earthcentric philosophy and the capacity of designers to transform these integrated forces into a new visual language’ (Wines 2000: 236).