In response to the spread of COVID-19 in early 2020, schools across the UK moved to virtual teaching arrangements for the majority of their learners. Some localized school closures occurred in England in February 2020, with a national lockdown following in March 2020. Although relaxed in June 2020, concerns about rising cases of the virus led to a second period of enforced school closure across the UK in January 2021. With no sign of the pandemic abating, we wanted to gain insights into teachers' experiences at this unique time. We used a solicited diary method with teachers over a 4-month period to reflect on workload and wellbeing issues related to their changing teaching practices. The diaries were supplemented by a series of teacher interviews. In this paper, we carry out a critical reflection of diary use. We observe how diaries provide a structure for eliciting ideas in an ordered way, and which then become a resource for a teacher's professional reflection. This process also appears to strengthen some of the social connections that were compromised during the social distancing periods of the pandemic, and which has benefits for teachers' wellbeing.