This qualitative study investigates how three experienced Native English-speaking teachers (NESTs) in Korea’s private education sector (hagwons) construct and negotiate their professional identities. Grounded in Wenger’s (1998) social theory of identity, the study explores (1) how NESTs navigate their roles across institutional, cultural, and global communities of practice, and (2) how their learning trajectories influence identity development over time. Data were collected through group discussions, reflective journals, and in-depth interviews. Findings reveal that NESTs’ identities are dynamic and continually reshaped through interactions with Korean English Teachers (KETs), students, and institutional contexts. While native-speaker status affords symbolic capital and instructional autonomy, it can also result in marginalization within Korea’s exam-oriented, hierarchical education system. The study highlights how sustained engagement, intercultural adaptation, and reflective practice foster more agentive and contextually grounded professional identities. It calls for institutional policies and teacher education programs that support long-term development, promote equitable team-teaching, and provide localized training responsive to the specific demands of Korean English classrooms.