In this in-class activity, organic chemistry undergraduates try to place an assortment of molecules in chronological order from oldest to most recently synthesized. In the students' first attempt, they use their knowledge of reactions and synthesis to analyze the organic compounds for their structural complexity. Before a second attempt, the names of the molecules are revealed, most of which are familiar (e.g., ibuprofen, morphine). The historical setting of these common molecules is now prioritized in the students' second attempt at ordering, before the correct chronological order is unveiled. The activity allows students to step away from the daily grind of dense organic chemistry content and provides an opportunity to see the subject from a bigger-picture perspective. Designed with the purpose of allowing students to explore their curiosity and make connections, the entrepreneurial-minded learning (EML) activity is specifically targeted toward the pre-health (nonchemistry major) students that make up the bulk of most organic chemistry cohorts. Pre-and post-activity survey results show that the students find the activity useful and engaging and that it succeeds in helping them connect the subject to a broader, real-world context.