This cross-sectional study explores the connections between resilience, work engagement, proactive strategies and personal resources among Italian kindergarten and primary school teachers. It specifically seeks to determine if and how personal resources can foster teachers’ work engagement, resilience, and proactive strategies at work. The study was conducted using a sample of 183 full-time, in-service kindergarten and primary teachers at public schools in Italy. Data were collected through self-report questionnaires, including the Brief Resilience Scale, the Ultra-Short Measure for Work Engagement, the Proactive Strategy scale, the Self-Compassion Scale, the Life Orientation Test-Revised, the Experienced compassion at work scale. Data were analyzed using a path analysis model. Results indicated that teachers’ self-compassion was positively associated with the use of proactive strategies and perceived received compassion was strongly related to work engagement. Moreover, higher levels of self-compassion were linked to greater work engagement. Teachers’ optimism and self-compassion were both positively associated with resilience, whereas self-criticism showed a significant negative association. Our research supports the need for educational policymakers and school leaders to focus on personal resources and work-related well-being.