© 2018 John Wiley & Sons Ltd. This chapter focuses on detail research work with people with dementia, whose forays into creative activity and constitutes a form of resilience in their experience. It describes briefly a number of different design projects with different populations, all living with illness, disability or otherwise facing difficult times in their lives. The chapter also discusses the challenges of living as a homeless person, and takes a look at the appropriation of technologies that this population uses to maintain its own wellbeing, as well as a series of studies that detail the complexities inherent in carrying out a research process with a group of people whose circumstances change daily. The chapter ends with some critical points on designing with people facing challenging circumstances as well as solidifying some of the more salient themes running through these projects as ways forward when designing with this population.