Social ecologists, economists and epidemiologists note that systems are ‘leaky’ particularly at the stage of reorganization, therefore for long term research, the challenge is not to gather information over time but rather, to measure in time, particularly with relation to collective memory and lagged effects. Similarly art and design research with an ecosystem approach has seen a shift in attention from a subject’s location in space toward an understanding of the subject being duration in time. These drawings explore various experiments into this approach at Parsons the New School for Design in 2009 and 2010. Consciously seeking alternatives to geographical mapping the city as an object in space, the classes used perceptive readings of territorial shapes, cinematically inspired and cybernetically based drawing methods to develop drawing systems to draw systems. The classes found two interlinked and emergent patterns of reorganization; the centralizing force of a designed urban fragment and the distributive effects of everyday biophysical design acts by individuals and social organizations. The students reflect on shared questions that resonate globally: what happens if the structure and dynamics of human-ecosystems are modeled as creative rather than something that can be predicted, maintained or controlled?