Design has the potential to include or exclude people, depending on how user needs are translated into products. Design exclusion has been vast in design for health care. Medication packaging design is a common example. It does a good job of protecting the product but can result in creating difficulties when used, especially for those who are older. Research in this area lacks an inclusive and user-centered approach because potential users have been studied outside of their context of living and with methods that limit participation. The aim of this study was to explore the combined use of solicited diaries and photography to engage and include older users in gathering data and reflecting on their day-to-day experiences of using multiple medications and the medication packaging. Our findings show key learnings of using this combined method, as well as related methodological challenges, and provide recommendations to tackle these challenges. The use of solicited diaries with photographs taken by participants is deemed to be relevant in interdisciplinary fields of research and practice, where designers and other professionals aim to better understand the reality of older people and create meaning in their experiences of self-care.