The authors surveyed 207 late adolescents on measures of new economy career orientation (protean and boundaryless career orientation), career adaptability (planning, self-exploration, environmental exploration, decision making, and self-regulation), disposition (proactive disposition), and environmental support (social support) and hypothesized (a) that new economy career orientation would be associated with career adaptability, disposition, and environmental support and (b) that career adaptability would mediate the relationship between disposition and career orientation and between environmental support and career orientation. The main predictor of new economy career orientation was self-regulation, which also mediated between proactive disposition and career orientation. Planning predicted one aspect of boundaryless career (mobility preference), while social support predicted a second (boundaryless mind-set). Overall, the results suggest that adolescents with higher self-regulatory skills, social support, a tendency to not overplan, and a disposition to be proactive, will be more positive toward changing work environments. (Contains 2 figures and 2 tables.)