At the end of the last century, digital technology emergence enabled millions of people to compete globally by remotely offering their knowledge and skills. In addition, business processes are becoming fragmented into smaller components, so-called short-term projects. These work arrangements are often carried out by so-called independent professionals (contractors), better known as freelancers. A literature review has shown that the research topic of freelancing from an entrepreneurial perspective is relatively new and has its assumptions and gaps. Different stakeholders and institutions connect, mediate and manage the services of the entrepreneurial ecosystem to support entrepreneurs. As freelancers belong to the self-employed entrepreneurial category, they are engaged in business activities and need support from their environment. To contribute to this topic, we have analyzed the relationships between freelancers’ job and career satisfaction, digitalization and entrepreneurial ecosystem factors, with the aim of making policy recommendations. Regarding the entrepreneurial environment, we analyzed the cultural and social norms and government programs that provide support, based on the measurement instrument, developed in the Global Entrepreneurship Monitor (GEM) research. We surveyed 200 freelancers (respondents) in Slovenia. Using factor analysis and structural equation modelling, the empirical results suggest that digitalization and cultural and social norms are significant factors that promote the success of new careers as freelancers in terms of job and career satisfaction. The results show that both positively influence job and career satisfaction, while government programs indirectly influence the job and career satisfaction of freelancers. This explains how the entrepreneurial ecosystem, plays a special role in supporting freelancers on their career path.
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