The objective of this study was to explore the relationship between courage and tolerance of ambiguity among young adults when making career decisions. It also aimed to determine whether life orientation—categorized as either transitive or moratory—serves as a moderating factor in this relationship, and to what extent. The study included 229 participants, consisting of 145 women and 84 men, aged 19 to 26. Courage was measured using a custom-adapted version of the Courage Scale, and tolerance of ambiguity was assessed with the Tolerance of Ambiguity in Career Decision Making Questionnaire. Life orientation was evaluated using the KPS-S2 Social Participation Questionnaire. Results indicated that both moratory and transitive orientations significantly moderated the relationship between courage and tolerance of ambiguity. Specifically, an interaction between low to medium moratory orientations and courage, as well as between medium to high transitive orientations and courage, was observed. In both scenarios, this interaction was associated with an increased aversion to tolerance of ambiguity.