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Recent evidence shows that the frequently proclaimed collapse of the traditional career model is actually not supported by job tenure data. This paper argues that the observed stability of job tenure might be explained by an increasing number of shamrock organizations. This organizational form has three types of workers: core employees, professional freelancers, and routine workers. In such an organization, two very different career models coexist. The organization largely determines the career of the core employee, whereas the individual essentially shapes that of the professional freelancer. This paper studies extensively the career of this second group: the professional freelancer, a growing phenomenon in many developed countries but not yet the focus of many career studies. We develop a freelance career success model on basis of the intelligent career framework augmented by insights from literature on entrepreneurship. Data are from a web survey with responses from about 1600 independent professionals in the Netherlands, in combination with 51 in‐depth interviews. We provide two main contributions. First, we report findings from the first large‐scale quantitative study into freelance career success. Second, this study enhances our understanding of the success of the modern career by building bridges between career and entrepreneurship literatures. We conclude that the external environment in which an individual freelancer operates is the most important factor determining career success. The study therefore suggests that more work needs to be performed on the relationship between the environment and individual career success.