The GAME 2019 #FuturistForum involved an exchange of ideas and perspectives on the future of learning in healthcare and necessary evolutions to sustain future health systems. This event allowed for reflection and discourse around a) what medical learning or learning in healthcare may look like 10–15 years from now, b) how technology would impact that evolution, and c) what collaborative roles distinct stakeholders would play. Seventy-five (75) key stakeholders, experts from various fields, participated in the two-day event. Four multifaceted themes were uncovered from the qualitative analysis, which are: learning will be lifelong and outcome-based, the health system will follow a preventive care model, technology will be an enabler of evolution in education and health systems, and that multi-level collaboration will support and sustain future progress. Future implications, exacerbated by the ongoing COVID-19 pandemic, and study limitations are described.