This article investigates how personality traits influence financial and nonfinancial career satisfaction, as well as overall life satisfaction, among freelancers in Slovenia. Using structural equation modelling (SEM), the study reveals that proactiveness and self-efficacy are strong predictors of financial satisfaction, while openness to experience, conscientiousness, and self-efficacy positively influence non-financial satisfaction. It is noteworthy that non-financial satisfaction significantly increases overall life satisfaction, while financial satisfaction alone does not. The study concludes that non-financial aspects of career satisfaction are crucial for the overall life satisfaction of freelancers. These findings highlight the importance of fostering certain personality traits to improve freelancers' wellbeing and career success. The study offers practical implications for career development programs, strategies to support freelancers as entrepreneurs, and policy recommendations to create an enabling environment for freelancers.