Due to advances in treatment and people's living longer, chronic diseases are becoming more common among our population. This is a leading contributor to the increasing burden on our current healthcare system. To reduce this burden and sufficiently meet the needs of this growing segment of the population, healthcare organizations must encourage the elderly to take a more active role in caring for their own health and well-being. Technology may offer a solution to this shortcoming. "Positive Technology" focuses on the use of technology for improving the quality of our personal experience, and it suggests specific strategies for modifying/improving each of the different dimensions involved - Emotional Quality (affect regulation); Engagement/Actualization (presence and flow); Connectdness (collective intentions and networked flow) -and for generating motivation and engagement in the process. "Transformative Technology" are technologically-mediated experiences that support positive, enduring transformation of the self-world. The transformative content is delivered through a set of experiential affordances, which are stimuli designed to elicit emotional and cognitive involvement in the designed experience: (i) emotional affordances; (ii) epistemic affordances. The paper discusses discuss the possible role of positive and transormative technologies for healthy living and active ageing by presenting different practical applications of this approach recently developed by our team.