For the last five years, the lives of New York City (NYC) public school educators have been governed by constant change. With certainty, every January or June heralded something new--restructured departments and offices, staff changes and new initiatives. One of the most interesting chapters in the history of the NYC school system unfolded in the spring of 2003 when Mayor Michael Bloomberg and schools Chancellor Joel Klein embarked on a major reorganization of the NYC Department of Education named the Children First Initiative. Its primary goal was to create more than 1,400 great schools. To make this a reality, 32 community school districts and high schools were organized into 10 regions, with each region overseen by a regional superintendent. The restructuring of the NYC Department of Education created numerous new positions that were not clearly defined, with staff members not certain of their own and others' changed roles and responsibilities. Regional offices were left to interpret, negotiate and realign former policies to the changes stemming from the central system. In this article, the author describes her experience working at the Department of Education beginning in midsummer 2003 as the special assistant to the regional superintendent. She spends the first few months of her job on the periphery, observing the organization and its members. While she knows she is responsible for supporting the region in developing programs and initiatives, it is not clear to her what that entails. Like others in the region, she is learning the landscape of the new organization and where she fits. Coming to the system fresh, she was compelled to learn, observe and participate in creating; the regional office became her play area and laboratory. By the time she moves to another borough, she is less enthusiastic and certain that her time is limited to one school year, affecting her energy and willingness to participate in the organization.