The rapid change towards a skills-based economy and new-collar jobs has been underway for years as both employers and employees adapt to new economic patterns reflected in the changing nature of work itself. Approaches to work and education have both changed to reflect that we no longer have one career, but many. The current approach to the talent market and education system for both job seekers and employers is stressed in handling the challenges of rapidly reskilling and re-employing workers at the same pace as changes in jobs. As we reimagine the workforce of the future and how to keep everyone’s skills current and relevant, there is a need to use advanced technology strategies such as learning and employment records, blockchain, augmented intelligence, and advanced analytics tools to help people navigate these changes. Our goal needs to be to empower tens of millions of learners to pursue and manage both their education and careers and greatly improve the way in which job seekers and employers connect.