The fiftieth anniversary of Geographical Analysis occurs for many quantitative human geographers at an exciting era of new and exciting sources of data and computational advancements. However, it also represents a crossroads where excitement to quickly capitalize upon these new data sources and methods risks reverting the discipline back to its abstraction‐rich and overly generalized roots, erasing much progress made in the pages of this journal that advocated for the recognition of individual differences and need for alternative and even qualitative data sources. In this commentary, I reflect on what we can do over the next 50 years to ensure that the journal is producing research that is socially impactful and better able to explain the messiness of social reality.