Our modern society has been transformed by the arrival of the digital era -computers, communication and the impending era of cognitive computing. The roots of this digitalization transformation are deep and extensively distributed through our United States society, as well as globally. Healthcare likewise has evolved and is well launched down this digitalization journey. This chapter is written from the perspective of a practicing surgeon with over 25 years of experience, based in an academic medical center and who has also been actively engaged in EHR adoption locally as well as numerous international telehealth and EHR collaborations. The chapter reviews how our modern healthcare system has adopted six transformative core competencies -EHRs, communication, telemedicine, analytics, data/security, and the virtual point of care (healthcare takes place in the cloud). The aggregate result of these forces is immense lever forcing the transformation of healthcare far beyond economic reform as envisioned by federal policy changes. The digital era is an unstoppable and empowering driver of healthcare that will be best seen in the near future through advances in EHR functionality, streaming analytics, virtual care teams and remote monitoring. In this era of tremendous uncertainty in healthcare it is the digital evolution of our society throwing healthcare a proverbial digital lifeline of survival.