Pharmacy education routinely asks learners to become confident decision-makers, yet confidence alone provides little information about whether a decision is defensible. A learner may be confident and correct, confident and wrong, uncertain despite adequate competence, or appropriately hesitant because the available information is incomplete or the consequences of error are substantial. Educationally useful confidence therefore depends on calibration: the correspondence between a learner’s confidence judgment and demonstrated performance. Knowledge, reasoning, verification, and supervision provide complementary evidence about whether independent action is justified. This Commentary examines calibrated confidence as a set of separable educational competencies. It distinguishes recognition of uncertainty from tolerance of uncertainty, verification from information retrieval, and escalation from generalized lack of confidence. It further argues that the appropriate response to uncertainty changes with the nature of the information problem and the consequences of an incorrect decision. Learners should be able to identify what remains unknown, select an appropriate source or verification strategy, explain the limits of the resulting evidence, and determine whether independent action remains defensible. Assessment should therefore sample more than confidence or final-answer accuracy. Cases, observed clinical encounters, source-retrieval tasks, reasoning explanations, reflective calibration, and supervision judgments can provide complementary evidence about different parts of the decision process. The educational objective is neither maximal confidence nor habitual caution, but appropriately supported independence.