Past research indicates that residency decision-making creates stress and anxiety for many students. This session documents the development of an innovative and data-driven approach undertaken at Des Moines University (DMU) to better address residency preparation using ePortfolios to support career choice and faculty advising. The ePortfolio encompasses four-year, longitudinal development of a curriculum vitae, exploration of medical careers, assessment of personal self-care and wellness, reflection on professional identity, and support of the residency application and interview. Lessons learned and outcomes of the strategic planning process and project implementation will be shared.