Many experts have foretold of a digital transformation in medical education. Yet, until recently, day-to-day practices for frontline clinician-educators, who cherish close physical and intellectual contact between the patient, learner, and teacher, have remained largely unchanged. The COVID-19 pandemic disrupted that model and is forcing teachers to pursue new ways to reach learners. We provide a roadmap for educators to start their transformation from an analog to a digital approach by harnessing existing tools including podcasts, social media, and videoconferencing. Teachers will need to enhance the same pedagogical and interpersonal practices that underpin effective in-person education while they learn new skills as they become curators, creators, and moderators in the digital space. This adaptation is essential, as many of the changes in medical education spurred by COVID-19 will likely far outlast the pandemic.