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This study identified factors associated with the decision to enroll in a higher education degree program. In the context of predicting enrollment in a workforce development credentialing program, this study identified six variables that are strongly related to the likelihood to enroll: time out of school; possibilities for intellectual, personal, and career opportunities; institutional support; synchronizing learning and earning; reflective learner; and match with an academic reputation. Results suggest that enrollment is the result of an interaction among situational, occupational, and institutional factors rather than primarily a desire or need to acquire knowledge as a commodity. The decision to enroll in a long-term commitment is a negotiated activity in which self-interests are balanced among various other interests, including the employer, family, friends, and identity as a learner. This study contributes to the literature by suggesting that time out of school is strongly related to the decision to enroll. (Contains 1 table and 2 figures.)