Self Determination Theory (SDT) asserts aspirations (life goals) of personal growth, relationship and community (intrinsic aspirations) support wellbeing, whereas aspirations for wealth, image and fame (extrinsic aspirations) is detrimental. The following study explores aspirations on a sample of 386 leaders towards job satisfaction, and also testing the differences by leadership position (senior and junior). Findings show that all aspirations are related to job satisfaction, with extrinsic aspirations negatively related and intrinsic aspirations positively. Regression analysis showed that significant predictors were image aspirations (negatively) and personal growth aspirations and relationships aspirations (positively). In addition, the majority of interaction effects were significant showing that senior leaders enjoyed greater job satisfaction than junior leaders, regarding most aspirations. This study is important as it highlights the positive nature of intrinsic aspirations and the negative influence of extrinsic aspirations. Furthermore, it highlights the importance of a senior leadership position for leveraging aspirations towards superior job satisfaction.