After the tourism boom in Phuket, Thailand around the 1980s, there was an emergence of massive in-migration of tourism-related labor from different parts of the country. Some found work in different kinds of careers accessible within the system, which would contribute and generate a huge income for labor and the nation. However, this income is characterized by fluctuations and unpredictability － factors that push the government to frequently issue policies to regulate such occupations. This paper aims to discuss the ambivalent practices of government and labor in the tourism sector through focusing on the concepts of formality and informality. The study further analyses the attributes of the career of a freelancer tour guide; the purpose of the policy regulating the tour guide license; and the tension among the tourism market, the freelancer tour guides, and the government. It tries to propose an alternative approach to discussing informality, which can deepen the understanding of the dynamism of contemporary flexible labor.