This third brief in the series invites us to consider the nature of expertise in the context of supporting marginalized and vulnerable workers to thrive in our rapidly changing landscape of work. In the context of such change, information that is relevant to a given problem space within a certain time horizon is dynamic. To thrive at this pace of change, humans must know how to obtain and restructure information, to let go of information that is no longer useful, and to repurpose information between contexts. Deep knowledge of specific domains is important for grasping nuance and complexity, yet it is also important to know how to learn about new domains and to apply knowledge flexibly across domains. This brief introduces the concept of adaptive expertise—an ability to think flexibly, adapt to varied contexts, and to gain new understandings. Like a spider weaving a web, adaptive expertise allows one to build from what is in one’s grasp to cast out into new terrain and to new make connections. It contrasts with classical expertise, which involves deep knowing within a subject matter area. While classical expertise is important, it can be siloed; we argue that adaptive expertise is a critical component of high-level performance in a changing world. Based upon research in cognitive, neuro-, and the learning sciences and building upon the agentive and dispositional vision of the learner in the first and second briefs, this third brief argues that Next Level Learners engage in six tendencies related to Adaptive Expertise. These enable thinking flexibly, orienting to new areas of knowledge, gaining new understanding effectively and efficiently, and being aware of contexts and cultures of knowledge. Adaptive expertise supports our asset-based focus on leveraging prior knowledge and skills in workforce development, rather than one of “starting over” as communicated by the term “reskilling,” and can play an essential role as people increasingly need to orient to new bodies of knowledge and competencies.