This paper describes the investigation of the development of future technological products to support older people in everyday living through the agency of a community art group. Recent research has identified a number of challenges facing designers seeking to use traditional participatory design approaches to gather technology requirements data from older people. Here, a project is described that sought to get a group of older people to think creatively about their needs and desires for technological support through the medium of paint. The artistic expression technique described in this article allowed the identification of issues that had also been found by previous research that used a range of different techniques. This indicates that the approach shows promise, as it allows information to be gathered in an environment that is comfortable and familiar using methods already known by the participants and which they find enjoyable. It provides a complement (or possible alternative) to standard protocols and has the potential benefit of extracting even richer information as the primary task for participants is enjoyable in its own right and is not associated with an interrogative process. Furthermore, it is argued that some of the key risks of traditional approaches are lessened or removed by the naturalistic setting of this approach.