Purpose To gain a deeper understanding of healthcare workers experiences during COVID-19 using an anonymous, web-based, audio narrative platform. Methods Data were collected from healthcare workers in the midwestern United States using a web-enabled audio diary approach. Participant recordings were analysed using a narrative coding and conceptualization process derived from grounded theory coding techniques. Results Fifteen healthcare workers, in direct patient care or non-patient care roles, submitted 18 audio narratives. Two paradoxical themes emerged: 1) A paradox of distress and meaningfulness, where a harsh work environment resulted in psychological distress while simultaneously resulting in new rewarding experiences, sense of purpose and positive outlooks. 2) A paradox of social isolation and connection, where despite extreme isolation, healthcare workers formed intense and meaningful interpersonal connections with patients and colleagues in new ways. Conclusions A web-enabled audio diary approach provided an opportunity for healthcare workers to reflect deeper on their experiences without investigator influence, which led to some unique findings. Paradoxically, amid social isolation and extreme distress, a sense of value, meaning and rewarding human connections emerged. These findings suggest that interventions addressing healthcare worker burnout and distress might be enhanced by leveraging naturally occurring positive experiences as much as mitigating negative ones.