The goal of this study is to examine the impact of self-leadership styles on the dimensions of entrepreneurial orientation in organizations in Dubai and the Netherlands: Innovativeness, Risk Taking and Proactiveness. The study also distinguishes the impact of self-leadership styles and entrepreneurial orientation on the dimensions of creativity and productivity. A path analysis was performed, applying SEM, using AMOS. The following four hypotheses were tested: 1. The greater the level of opportunity thinking thought pattern strategies, the greater the level of entrepreneurial orientation. 2. The lower the level of obstacle-thinking thought pattern strategies, the greater the level of entrepreneurial orientation. 3. The relationship of the opportunity thinking strategies with creativity will be stronger than that with the obstacle-thinking strategies. 4. The relationship of the opportunity thinking strategies with productivity will be stronger than that with the obstacle-thinking strategies. Overall support was found for hypotheses 3 and 4. Hypotheses 1 and 2 were partly supported.