Along with technological progress, vocational education and training (VET) is consistently changing. Workforce disruption has serious consequences for workers and international economies, often requiring adults to transition into different occupations or to upskill to maintain employment. We review recent literature covering VET trends, theoretical considerations for the 21st century, and present an approach to workforce training to help workers not only learn necessary skills but also become adaptable to constant change. We suggest a functional contextualist approach to mastery learning achieves this aim. Specifically, we offer suggestions for pedagogy that not only develop skills but also encourage higher order thinking. Within a novice to expert continuum, we suggest deliberate practice, mental simulation, and reflective meaning making as methods to achieve efficiency and transfer-learning outcomes relevant to a changing workforce. This approach recognizes that learning is context bound and should promote broader human capabilities that support both employability and the continuing development of life literacies.