As twenty-first century careers become more flexible, interest-oriented, and self-directed, the clarity of career goals alone is no longer sufficient. To better prepare students for the future world of work, engagement in proactive career behaviours is essential. The present study investigated the predictive relationships of career goal clarity, proactive career engagement, and positive student outcomes across two large-scale samples of Secondary students in Singapore. Among 16-year-old students, 10% (n = 1,166) have not decided on their career goals while the proportion was 22% (n = 867) among 15-year-olds in Study Two. Structural equation modelling indicated positive effects of career clarity on proactive engagement and students' confidence in future outcomes (Study One). Study Two extended the findings by examining a different outcome variable--inventive thinking. Consistent results from both studies extend the external validity of the measures used. Across both studies, engagement in proactive career behaviours acts as a psychosocial buffer against low career clarity in the attainment of positive student outcomes. As proactive behaviours involve intentional self-regulatory processes that lie at the cornerstone of motivational and self-cognitive social theories, the findings of this research may well generalize to other research domains in terms of how the regulation of goals influence positive outcomes.