Planners worldwide are exploring ways to regenerate shrinking cities, varying from pro-growth strategies with the aim of reversing population losses, to strategies that manage urban decline by adjusting the built environment to a smaller population. However, both approaches are reactionary rather than anticipatory, addressing decline after substantial shrinkage has happened. This paper examines the relationship between place identity and attachment and urban shrinkage, arguing that reinforcing place attachment based on building a strong local identity can help cities reduce the negative consequences of shrinkage. We propose an identity-building method that can become the base for design strategies fostering place identity and attachment. The paper applies this method to Chōfu, one of Tokyo’s bedroom towns, which is currently developing strategies to anticipate its future shrinkage. The method collects the radically exterior perceptions of international visitors to trigger conversations with local stakeholders with the final aim of finding critical elements to consider when developing design strategies to anticipate decline. Policymakers and planners are better advised to consider alternatives to business-as-usual approaches to shrinkage, so that regeneration strategies can be more significantly linked with the specifics of the place and how it is perceived, achieving a higher attachment and involvement with residents.