Previous research has suggested that there is a strong and positive relationship between being an entrepreneur and possessing a high degree of subjective well-being as well as job satisfaction. The big five personality traits have also been argued to be significantly related to both subjective well-being and job satisfaction. Little is however known if personality affects entrepreneurs and regular employees differently. In this paper the impact of personality traits on the cognitive part of subjective well-being as well as job satisfaction are investigated separately among entrepreneurs and regular employees. This is done through OLS-regressions using a Swedish nationally representative survey Employment, Material Resources, and Political Preferences (EMRAPP), where entrepreneurs were oversampled in order to be able to compare entrepreneurs (N = 2483) and regular employees (N = 2642). The findings suggest that there is no substantial difference between entrepreneurs and regular employees when looking at the relationship between personality traits and subjective well-being. Findings on job satisfaction on the other hand showed that the personality trait openness to experience had no impact on job satisfaction, and that the personality trait emotional stability (neuroticism reversed) was equally beneficial for both entrepreneurs and regular employees. Extraversion had a positive relationship with job satisfaction among both entrepreneurs and regular employees, although the relationship was twice as strong among entrepreneurs. The personality traits agreeableness and conscientiousness on the other hand were only related to job satisfaction among entrepreneurs. Personality traits are thus much more important for job satisfaction among entrepreneurs.