America’s workforce is on the cusp of momentous change as technology and demographic change transform the nature and availability of work. Robots and algorithms present increased competition to workers, but also hold the promise of augmenting human labor and intellect. Meanwhile an ageing workforce, the sharing economy, and diminishing employer commitments are hastening a move toward short-term, flexible work in the “gig economy”. How might these changes redefine our understanding of career, education, and retirement? Can policymakers and corporations prevent today’s workforce revolution from widening inequality?