This project was carried out by the author in the summer of 2001 in New York. It comprises episodes that entail the sketch of a specific place, two sketches of the city traveller at that location who volunteered to be sketched and the author’s journal entries on each episode following the experience. One sketch is kept by the participant and the other by the author, which is presented in this paper. Since the boundaries of the project are fluid, it is formed and re-formed through the unfolding of each encounter. This paper provides an inquiry into the encounter between self-other-environment created and transformed by the project.