This article examines the intricate interplay between structural form and semantic content in paremiological units (commonly known as proverbs) that articulate concepts of work and business acumen. Employing an ethnolinguistic approach, the analysis delineates how proverbial structures reflect culturally embedded notions of diligence, prudence, innovation, and financial wisdom in English and related languages. Focusing on examples from the twentieth and twenty-first centuries, the study establishes a criterion for typologically categorizing these paremiological units and elucidates the interplay between structural features and semantic content. This article has explored the structure-semantic features of paremiological units expressing work and business acumen through a culture linguistic lens. By analyzing 12 representative examples predominantly from the twentieth and twenty-first centuries, the discussion has shown how these commonly used proverbs encapsulate core cultural values and economic principles. The dual-axis typology—anchored in structural patterns and semantic content—provides a systematic framework for understanding how linguistic constructions carry significant cultural weight in orienting behaviors in the work and business domains.