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The purpose of this study is to examine how becoming a formal teacher leader affects teachers’ labor market trajectories. Using administrative and survey data from Tennessee, we use a combination of school-by-year and teacher fixed effects to examine the ways in which teachers who become instructional coaches or peer observers are more or less likely to move schools, leave the teacher and administrator labor market, and become school administrators. Becoming an instructional coach or peer observer increases the probability that the teacher will remain in teaching or become a principal or assistant principal. Subgroup analyses indicate that early-career instructional coaches and peer observers and peer observers of color drive the relationship with becoming an administrator.