This thesis presents a conceptual and empirical investigation of why some individuals and not others enact opportunities. It takes a distinct view of opportunities – enacted possibilities of economic gain – thereby bridging economics and psychology perspectives. In the developed theoretical model, opportunity enactment is an ideal type construct involving distinct configurations of information context, learning style, and specific human capital. Three categories of information context – demand-driven, supply-driven, and replication-driven – capture the environmental requirements imposed on individuals in conceiving of future possibilities. Learning style and specific human capital convey the uniqueness of an individual’s prior experience. The former represents a developed pattern of interaction with one’s environment, while the latter reflects one’s stock of domain-specific knowledge. The model is tested in an experimental setting and further corroborated with data from the Panel Study of Entrepreneurial Dynamics. The thesis outlines a number of theoretical and methodological contributions, directions for future research, and implications for practice.