In the move toward competency-based medical education, leaders have called for standardization of learning outcomes and individualization of the learning process. Significant progress has been made in establishing defined expectations for the knowledge, skills, attitudes, and behaviors required for successful transition to residency training, but individualization of educational processes to assist learners in reaching these competencies has been predominantly conceptual to date. The traditional time-based structure of medical education has posed a challenge to individualization within the curriculum and has led to more attention on innovations that facilitate transition from medical school to residency. However, a shift of focus to the clerkship-to-postclerkship transition point in the undergraduate curriculum provides an opportunity to determine how longitudinal competency-based assessments can be used to facilitate intentional and individualized structuring of the long-debated fourth year. This Perspective demonstrates how 2 institutions - the University of Virginia School of Medicine and the University of Michigan Medical School - are using competency assessments and applying standardized outcomes in decisions about individualization of the postclerkship learning process. One institution assesses Core Entrustable Professional Activities for Entering Residency, whereas the other has incorporated Accreditation Council for Graduate Medical Education core competencies and student career interests to determine degrees of flexibility in the postclerkship phase. Individualization in addition to continued assessment of performance presents an opportunity for intentional use of curriculum time to develop each student to be competently prepared for the transition to residency.