Clerkship grades (like money) are a social construct that function as the currency through which value exchanges in medical education are negotiated between the system’s various stakeholders. They provide a widely recognizable and efficient medium through which learner development can be assessed, tracked, compared, and demonstrated and are commonly used to make decisions regarding progression, distinction, and selection for residency. However, substantial literature has demonstrated how grades imprecisely and unreliably reflect the value of learners. In this article, the authors suggest that challenges with clerkship grades are fundamentally tied to their role as currency in the medical education system. Associations are drawn between clerkship grades and the history of the U.S. economy; 2 major concepts are highlighted: regulation and stock prices. The authors describe the history of these economic concepts and how they relate to challenges in clerkship grading. Using lessons learned from the history of the U.S. economy, the authors then propose a 2-step solution to improve upon grading for future generations of medical students: (1) transition from grades to a federally regulated competency-based assessment model and (2) development of a departmental competency letter that incorporates competency-based assessments rather than letter grades and meets the needs of program directors.