This paper focuses on the role of individualism in community organizing. My case study follows the organizing efforts of the Coalition for Affordable Northampton Neighborhoods (CANN) and residents’ attempts to save an affordable neighborhood from Smith College’s campus expansion. As a resident and co-founder of CANN I was particularly interested in identifying the reasons for our difficulty in organizing residents whose homes would be torn down. While attending community and city meetings, interviewing core activists and activists who left the organizing efforts, I observed individualism undermining community organizing and political involvement. People’s search for self-fulfillment was in conflict with the level of commitment necessary to sustain a social movement. Coupled with the “progressive politics” of a “Paradise City” where indulgent self-care permeates the culture, individualism emerged as an explanation for dwindling numbers of active residents. Identifying individualism as an issue for activists can provide much needed insight and subsequent action to address and solve the problem of erratic, unpredictable participation of individuals in political and community organizing. We can learn how to not only create, but also sustain strong social movements