There has been a shift in sociological research away from research “on” children to conducting research “with” children. Research with children should be guided by child-centric methodologies that put children’s strengths at the heart of the research design, which usually entails visual methods. This case study focuses on the benefits and challenges of using drawing diaries as prompts in semi-structured interviews to understand the experiences of young children by drawing upon data which were collected in 2016 as a part of a broader Australian study on childcare flexibility. We explain the theoretical framework and research strategy underpinning our use of drawing diaries. The benefits of a pilot study are highlighted and key ethical considerations are discussed. Finally, we unpack strengths and challenges related to using drawing diaries as prompts in semi-structured interviews.