This article explores entrepreneurial cognition theory and the boundaryless view of careers analyzing how a boundaryless view may be composed of several cognitive biases such as overconfidence, belief in the law of small numbers, and illusions of control focused on the ability to enter employment following entrepreneurial exit or failure. These biases reduce risk perceptions associated with the decision to start a venture; however, critical decision-making information may be missed by boundaryless biased individuals, such as negative attributions about former entrepreneurs made by recruitment managers.