The study aims to gain a better understanding of the interrelation between teachers’ proactive strategies (self- and co-regulation) and perceived teacher-working environment fit that would be mediated by a socio-contextual burnout experience. The results indicate that teachers can learn the kinds of strategies that allow them to reduce burnout and construct a better working environment fit. Furthermore, teacher’s co-regulation and ability to seek and receive social support from colleagues correlated positively with experienced teacher-working environment fit. Finally, the interrelation between teachers’ proactive strategies, both self- and co-regulation, and perceived teacher-working environment fit, is mediated by the socio-contextual burnout experience.