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This longitudinal study reports the descriptive journeys of high-performing urban California teachers and school leaders from pre-COVID (2018) through post-COVID (2023) within a phenomenological Grounded Theory design. Four purposive samples totaling 172 participants responded respectively to surveys and individual interviews aligned to four conceptual frameworks: Academic Optimism (Hoy, et.al. (2006); the Dunning-Kruger Effect (Dunning & Kruger, 1999); Psychological Safety (Edmondson, 2016); and Community Leadership (Pittinsky, 2006). Findings reveal there was no challenge too great for these educators as they both framed their most pressing issues outside of the dominant ways of thinking inherent to schooling and extended a community of care mindset while serving pre, during, and post-pandemic.