Overconfident CEOs overestimate their ability to generate value. We investigate how this affects divestiture activity and whether it moderates a CEO's investment lifecycle. We hypothesize and find that overconfident CEOs are generally less likely to divest units and their divestment decisions are less sensitive to career lifecycle concerns. In addition, after a divestiture overconfident CEOs spend more on capital expenditures (Capex) and acquisitions than other CEOs. Overall, our results suggest that overconfident CEOs prefer to retain units and divest largely to maintain an investment trajectory. Our results further highlight the important role behavioral traits such as overconfidence play in corporate decision-making.