Professionals are working in an increasingly diverse and fast evolving environment. Developments in technology and institutions are quickly destabilizing and reshaping the content, process and organization of professional work, resulting in more variety in work arrangements and environments. Some new forms of work are in strong contradictions with the dominant norms of the field, constituting counter-institutions where professionals construct counter-institutional identities (Chreim et al. 2019). Nevertheless, counter-institutional identity is a newly developed concept. Little is known about the individual-level identity work when professionals navigate a counter-institution and the consequences of identifying with the new work context. To advance the knowledge about counter-institutional professional experiences, I explore two research questions in this paper: What is the process in which individual professional workers identify with a counter-institution? How does workers’ counter-institutional identification affect their working patterns in a flexible work setting? To answer these questions, I conduct a case study on the rising online legal services in China. Bridging research on professional identity and online gig work, I discover that the degrees to which professionals identify with the counter-institution is determined by three assessments that they run: work-professional identity congruence assessment, work-needs congruence assessment, and work-personal value assessment. Depending on individuals’ counter-institutional identification and financial reliance on online work, are categorized into four groups with distinct purposes and working patterns: resistants, enthusiasts, hobbyists and reluctants. These findings enhance the understanding of professionals’ identity work and employment choices in the era of increasing flexibility in work arrangements.