The value of longitudinal designs in qualitative research is increasingly being recognised, though practical guidance in relation to them remains limited. In this case study we describe an ongoing longitudinal project examining the meanings held about outdoor spaces in the context of the COVID-19 pandemic. There is a large and growing literature on how contact and connection with the natural world affects people, but this is predominantly quantitative and concerned with wellbeing and functional outcomes, rather than meaning-making processes. The research this case study reflects upon used a mixture of data collection methods, mostly qualitative, and we focus here specifically on the use of written narrative “sketches” to explore personal meaning-making in relation to outdoor spaces. We describe the main challenges we have faced in relation to sampling and recruitment, participant engagement and retention, data management and research team coordination. We discuss the ways we sought to address these challenges, the extent to which these were successful, and draw lessons for those wishing to use similar longitudinal qualitative designs in their own research.