For decades, the geography of work in the United States has faced a seemingly intractable problem. On the one hand, agglomeration economies and the rise of large cities have led to smaller towns experiencing stark brain drain. The loss of young and highly educated residents to larger cities has had severely detrimental effects to the local economy and local sense of community in smaller towns. On the other hand, educated workers migrating from smaller towns to the larger urban clusters, often archetypal members of the “creative class”, have faced separation from their hometown communities and high cost of living in dense urban centers. As Moretti documents, this has led to reduced real income for college graduates migrating to large cities. In other words, while smaller towns have lost talent with no jobs to retain them, educated workers migrating to large cities have faced high cost of living and separation from their communities. In this context, the rapid rise of flexible “work-from-anywhere” (WFA) employment arrangements, where companies allow workers to relocate and live at the locations preferred by workers (Choudhury, 2020), has the potential to mitigate this problem. If indeed, WFA were to become a mainstream policy across multiple organizations, smaller towns might see a flow of workers who are able to work remotely migrating from larger cities. Workers migrating to cheaper locations might experience gains in real income and might also experience a stronger connection to their new communities. Sensing this, several localities across the country have rolled out programs to attract remote workers. Examples include Ascend WV in West Virginia, Remote Tucson in Arizona, and Tulsa Remote in Oklahoma.