Firms dedicate large portions of financial disclosures to updating and discussing their strategy and plans for the future, and investors often evaluate those plans after learning how the firm performed in the current period. I examine how current-period performance shapes investors’ beliefs about the appropriateness of managerial optimism which, in turn, affects their evaluation of firms that focus on either challenges or opportunities in future-oriented disclosures. I conduct three experiments that test my process theory. I hypothesize and find that a firm’s current-period performance shapes investors’ beliefs about whether managers can best achieve success by being more or less optimistic about the future. When a firm is performing poorly, investors believe that managers can best achieve success by being more optimistic and less realistic about the future, and therefore invest more if the firm focuses on opportunities rather than challenges in future-oriented disclosures. When a firm is performing well, on the other hand, investors believe that managers can best achieve success by being more realistic and less optimistic about the future, and therefore invest more if the firm focuses on challenges rather than opportunities. These results challenge the notion that investors always react positively (negatively) to disclosures that focus on opportunities (challenges). Instead, these results suggest circumstances in which managers can benefit by focusing on challenges, in order to signal a more realistic and less optimistic outlook about the future.