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Teachers regulate their felt and expressed emotions for instrumental and hedonic goals. The effect of teachers’ emotion regulation on well-being has been widely explored and discussed. However, previous empirical studies showed mixed results. The three-level meta-analytic study examined the relationships between teachers’ emotion regulation and well-being. Also, moderating effects were tested, including national culture, teaching contexts, and individual characteristics. Teachers who perceived themselves high ability reported higher well-being and lower ill-being. Regarding strategies, teachers who adopted cognitive reappraisal and automatic emotion regulation sensed better well-being than those who adopted expressive suppression. We introduced Hofstede’s cultural dimensions model and found certain dimensions moderated these links. Other moderators were also tested and discussed. The study provided insights for future research.