The current study investigated the dynamic interplay of career decision ambiguity tolerance and career indecision over 3 assessment times in a sample of college students (n = 583). While the previous research has repeatedly shown an association of career decision ambiguity tolerance with career indecision, the direction of this association has not been adequately assessed with longitudinal investigation. It was hypothesized in this study that there is a reciprocal pattern of career decision ambiguity tolerance leading to subsequent career indecision and career indecision leading to subsequent career decision ambiguity tolerance. Using a cross-lagged panel design, this study found support for the reciprocal pattern that aversion to ambiguity led to increased negative affect and choice anxiety in career decision making, while negative affect and choice anxiety led to increased aversion to ambiguity. Additionally, this study revealed that aversion led to decreased readiness for career decision making and readiness for career decision making led to increased interests in new information. The key findings were discussed with respect to the theoretical and clinical implications for career counseling along with limitations and suggestions for future research.