September 11th 2001 helped create a sense of ever-present risk for many Americans. At the same time, highly publicized abuses of corporate power and financial meltdowns in former Wall Street gems like Enron and WorldCom together with more recent economic trouble in the U.S. housing market heighten uncertainties. Although these events have hastened personal experience of insecurity across all socioeconomic levels, even in the dotcom glory days many middle-class families rightly sensed a threatening undercurrent of change. Although unsettling, global economic restructuring begun in the 1970s fueled stratospheric growth in the 90s as corporations embraced “flexibility.” On an individual level, the strategy has translated into lived realities of displacement. This chapter is based on five years of ethnographic fieldwork in the Midwestern United States among downsized and downshifting workers relocating to rural northern Michigan. It describes how, in the face of uncertainty, some people use the act of relocation to personally meaningful places as a way of redefining themselves and regaining a sense of control. In the wake of voluntary or involuntary career change, they attend to reordering work, family, and personal priorities according to an idealized lifestyle. Narratives presented involve what may be new expressions of old dreams, understandings, and ideals. Northern Michigan has long attracted people looking for at least temporary renewal in vacations and visits to second homes. Today, it finds itself destination for people seeking lasting refuge. Accounts of lifestyle migrants shared here are part of a larger moral story about what constitutes the good life in the United States at a time of shifting social categories and cultural meanings.