The New York City Zoning Resolution, while historically effective in regulating business locations, suffers from outdated regulations hindering the growth and expansion of local businesses. This study employs text analysis and diverse data sources to identify incongruities between businesses and zoning resolutions, revealing popular nonconforming activities like restaurants and entertainment venues. The analysis reveals the demand for local retail and services has exceeded the planned capacity in commercial and mixed-use districts. The spatial analysis also identifies areas like Bushwick and Park Slope-Gowanus with diverse nonconforming activities in C1 and R6 Districts. Recommendations emphasize the need for a smarter approach to updating uses as well as merging akin classifications to accommodate identical uses and reduce the “red tape” in the zoning regulations. Overall, this project aims to furnish a novel methodology for zoning analysis and provide recommendations to policymakers and planners in the zoning and economic development field.