This article proposes a pedagogy of well-being derived from the design of a high-impact practice (HIP) ePortfolio assignment. Research findings from a two-year pilot study revealed a recurrent trend that raised attention to the socio-psychological dimension that ePortfolios have on student learning and development. Teaching and researching during the COVID-19 pandemic served as a catalyst in this study. Moving forward from our pilot study (2020-2022), we (re)designed ePortfolio pedagogies to better address student well-being. Our research crystallized a realization that ePortfolio spaces bridge the personal, the academic, and the outward-facing, and due to their reflective nature, can open opportunities for self-observation, or making sense of experience in practical ways, and can even offer healing opportunities, resulting in a sense of catharsis for some students. We argue that the making of ePortfolios fosters well-being by asking writers to risk a new, tangible form of investigation that encourages radical reinventions of self. We dismantle the artificial binary that stigmatizes well-being as too personal and private for classroom inclusion. Our programmatic research advances dialogue about how ePortfolios repurpose authentic assessment of student learning over time.