The coronavirus disease 2019 (COVID-19) pandemic made it necessary for medical schools to restructure their curriculum by switching from face-to-face instruction to various forms of flexible learning. Flexible learning is a student-centered approach to learning that has received interest in many educational sectors. It is a critical strategy for expanding access to higher education during the pandemic. As flexible learning includes online, blended, hybrid, and hyflex learning options, learners have the opportunity to select an instruction modality based on their needs and interests. The shift to flexible learning in medical education took place rapidly in response to the COVID-19 pandemic, and learners, instructors, and schools were not prepared for this instructional change. Through the lens of the technology acceptance model, human agency, and a social constructivist perspective, I examine students, instructors, and educational institutions’ roles in successfully navigating the digital transformation era. The pandemic has also accelerated the use of advanced information and communication technologies, such as artificial intelligence and virtual reality, in learning. Through a review of the literature, this paper aimed to reflect on current flexible learning practices from the instructional design and educational technology perspective and explore emerging technologies that may be implemented in future medical education.