The Healthcare Information and Management Systems Society (HIMSS) conference convenes each year to bring industry thought leaders and practitioners together to discuss healthcare’s trending topics, emerging opportunities, and imminent challenges. HIMSS21 focused on the evolving needs of the healthcare workforce; the promise of, and impediments to, data-driven care; and the need to design care for the whole person, not personas. This report explains the industry’s notable evolutions over the past year and its trajectory toward a new paradigm of healthcare.