Careers can look straightforward on a CV—titles, employers, degrees—yet what really determines mobility is the evolving set of capabilities behind those labels: what people learn, what transfers, and what quietly stops transferring when opportunities shift. In this talk, I bring new measurements to that hidden layer. I translate millions of university syllabi into workforce-relevant skill profiles to compare what institutions teach to what jobs demand, and to see how the “same” credential can imply very different readiness depending on the skills it bundles. I then introduce Career Space, a representation that places education and jobs in a shared embedding to track occupation compatibility as something that grows, concentrates, or fades as experience accumulates—capturing the difference between pathways that keep many options open and those that build deep, targeted advantage. I close by looking at a higher-stakes pivot: cross-border mobility. Using large-scale career histories linked to origin-country conditions, I examine how women’s empowerment reshapes return versus stay decisions and how these choices redistribute knowledge production across countries.