Do freelancers feel they are insiders or outsiders in relation to organizations? In this study, we establish that both options may apply. The analysis of two waves of qualitative interviews indicates that highly skilled freelancers felt they were outsiders to client organizations and thus built explicit transactional psychological contracts to underline their position. Simultaneously, they perceived themselves as insiders to project teams, with whom they built open‐ended relational psychological contracts. Herein, we explain how and why this dual‐perceived insider status emerges, and we argue that it helps freelancers manage a distinctive challenge inherent in contract work, namely, the tension between being an independent actor and simultaneously integrating within a team.