Between 1999 and 2003, the Western Massachusetts Writing Project experienced a series of changes that made it question whether it could survive as a writing project site. The convergence of retirement, unexpected death, and withdrawal of long-term financial support forced the existing leadership to develop a process to look deeply into the work of the site and the people who supported that work. The result was the development of a set of tools that served as a guide toward broadening the leadership base, offering more purposeful programming, and creating a more sustainable site structure. This monograph describes how the losses experienced by the site forced site leaders to examine fundamental questions about the site such as, "Who are we?" and "Why do we do what we do?" These questions turned out to be the starting point for a focused inquiry that led to a site reorganization, which addressed the precipitating challenges while creating structures for facing future challenges, an experience that many sites are likely to have. What emerged from the assessment and planning process underscores the paradox of sustainability: the site must be dynamic in order to preserve its purpose and existence as an ongoing professional home for teachers, and simultaneously elastic enough to address the changing needs of a service area. By utilizing a focused inquiry approach along with tools such as the ongoing analysis of site maps and a site's Web presence, WMWP learned not to take existing leadership structures for granted and to constantly assess the assets and needs of the site. Other sites may face different kinds of challenges, but having a process in place for constant renewal helps them be better prepared for new challenges. Six appendixes are included: (1) Inservice Coordinator Job Description; (2) Western Massachusetts Writing Project Co-Director Job Description (3) Western Massachusetts Writing Project Technology Liaison Job Description; (4) Western Massachusetts Writing Project's (WMWP) Rotating Co-Director Site Map, 2004-2005 ; (5) Task Force/Co-Director Report; and (6) Western Massachusetts Writing Project Program Leader's Guide. (Contains 5 figures and 3 footnotes.)