Stagnating teacher salaries and the widening gap between public school teachers and similar workers have led to growing concerns that teachers will seek additional employment—possibly leading to teacher burnout and/or attrition in the process. Using data from the Schools and Staffing Survey and the National Teacher and Principal Survey from 1994–2021, we show that teacher multiple jobholding has been remarkably stable over time, although certain types of multiple jobholding have shifted. When examining the predictors of multiple jobholding, we found a high degree of variation across the timing, focus, and setting of teachers’ additional work. Using regression analysis, we show that teachers who work an additional job have higher levels of burnout but higher intentions to remain in teaching and lower rates of leaving. Differences in these outcomes are observed for teachers who work more than one additional job and teachers who work outside of school.