Advances in artificial intelligence and automation are transforming how people enter, navigate, and progress through the workforce, reshaping career pathways and eroding many of the traditional entry points into employment. This plenary examines how these shifts are redefining the relationship between learning systems and work, and the systemic questions they raise for education, access, and lifelong opportunity. By reframing how career pathways are evolving, the session invites reflection on what future-ready skills may matter most—and how education systems can remain responsive in a time of profound workforce transformation.