Abstract The terms of work have changed, with multiple transitions now characterizing the arc of a typical career. This article examines an ongoing shift in the area of vocational decision making, as it moves from a place where “it’s all about the match” to one closer to “it’s all about adapting to change”. We review literatures on judgment and decision making, 2-system models of decisional thought, the neuroanatomy of decision making, and the role of non-conscious processes in decision making. Acknowledging the limits of rationality, and the abundance of non-conscious processes in decision making, obliges us to act in ways that mitigate the inherent difficulties to which those processes make us vulnerable. We conclude that both rational and intuitive processes seem dialectically intertwined in effective decision making, and we offer a trilateral model of career decision making that includes rational and intuitive mechanisms, both of which are funded and kept in check by occupational engagement.