This study discusses stereotypes of entrepreneurship by looking at the overlapping areas of entrepreneurship, self-employment and professions. Professions are part of the category of self-employment and the study presents empirical findings drawn from a unique empirical dataset from Finland: a survey (N = 733) including freelance journalists, translators, interpreters and artists at the blurred boundaries between waged work and entrepreneurship. Findings reveal that the professions are clearly different and the manifestations of entrepreneurship vary, reflecting the work and the labor market situation within the profession. Life and work situations of liberal professions cannot be interpreted in simple black-and-white schemes of winners and losers. Instead, many different socioeconomic situations can be found ‘in between,’ which are driven by different social logics. For entrepreneurship research, the study opens up new avenues by taking us beyond the push-pull dichotomy, which over-simplifies the decision to enter self-employment. The term entrepreneurship is often used in an undifferentiated way, and it easily generates myths and stereotypes which are challenged by the study. A narrower and more realistic view shows that there are diverse agents under the flag of entrepreneurship, who are usually not regarded as core entrepreneurs although they exist in everyday life.