When individuals strive towards personal goals, they may encounter obstacles that could compromise their goal progress and pose a challenge to self–regulation. Coping with obstacles first requires those obstacles to be identified. The purpose of the present studies was to apply an inter–individual approach to this important, but insufficiently studied self–regulatory aspect of goal striving. We therefore examined the role of self–awareness, that is, paying attention to one's own feelings, thoughts, and behaviours, for the identification of goal–related obstacles. We measured and manipulated self–awareness in two correlational and two experimental studies (one of them preregistered) and asked participants to identify obstacles to their goals. All studies confirmed the hypothesis that individuals with higher levels of dispositional and situational self–awareness identify more obstacles, both with regard to their idiosyncratic personal goals (Studies 1 and 2) and with regard to a goal in an assigned task during an experiment (Studies 3 and 4). The results indicate that self–awareness plays a crucial role for identifying obstacles. We discuss the implications of our findings for personality and self–regulation research.