We surveyed 75 small, independent retailers in Chicago in 2018. We asked store owners and employees about their perceptions of neighborhood change and connectedness, and their views on retailing challenges like e-commerce, gentrification and government regulation. We found that most small retailers feel they are a part of their neighborhood even as most do not belong to an organization, their clientele are not neighborhood-based, and owners and employees tend to live outside of the neighborhood. We also found that most small retailers do not feel threatened by e-commerce. Complaints were confined to specific topics like parking and licensing fees as opposed to larger issues like gentrification or government regulation more broadly. Despite the common perception that mom and pop stores are struggling, respondents were overwhelmingly optimistic about the future.