Sustainability is a topic that has matured and has evolved from organisational sustain ability to societal sustainability and more recently to individual sustainability. As an individual is the core, basic component of society, and plays a critical role in societal transformation, there is growing interest and discussions on individual sustainability and wellbeing. Since the publication of Our Common Future – the report commis sioned by the UN General Assembly in tackling environmental and natural resources issues – the concept of ‘sustainable development’ has taken root in firms and govern ments, both in optimising their supply chain and in the planning of the sustainability of the society. However, counterintuitively, the fabric of the society – individuals and families – has been neglected in this journey of understanding their roles in sustaina bility, as well as in the nexus between their decisions and social outcomes. This thesis bridges the gap. Sustainability is a transformative process of improving the quality of lives by balancing various of our life aspects, such as economic, ecological, and societal dimensions. In this process, information systems often take a critical part as an analytical tool, which provides insightful decision support and recommendations based on collected data and information. In contrast to systems employed by corporates and governments, the development of sustainability systems for individuals and families is still in its infancy. Existing systems mostly are only focusing on one aspect of life and prescribe a single dimensional solution, without regard to the contextual and circumstantial complexi ties of life. In this light, this thesis aims to design and implement systems that adopt a holistic approach in understanding users’ individualistic needs, and in synthesising their life status and goals. The vision is to recognise the multifaceted aspirations of the users, and to nudge them toward a lifestyle that is sustainable, practical, and, above all, enjoyable. To realise this vision, the thesis adopts the multimethodological design science approaches (Hevner, March, Park, & Ram, 2004; Nunamaker, Chen, & Purdin, 1991) with the design eval uation methods from Hevner, March, Park, and Ram (2004) to address the challenges. ii First, the thesis defines individual and family sustainability and a set of nine principles named SSHARRPPP (Sustainable, Social, Holistic, Adaptive, Real-time, Real-world, Precise, Personalised, Persuasive). Based on these principles, the thesis develops sus tainable transformative processes that are applied to key activities and can bring fun damental changes for one’s life. From these conceptual and procedural foundations, the thesis designs system architectures and implements four systems as proof of con cepts. They are, namely, the SSHARRPPP Measurement, Shopping, Modelling, and Games. SSHARRPPP systems support individual and family sustainability holistically as they work together seamlessly. SSHARRPPP Measurement and Shopping measure key ac tivities that are performed by individuals and families. Based on the measured data, SSHARRPPP Modelling grasps causal effect relationships of one’s life dimensions and develops models. Lastly, SSHARRPPP Games helps people to stick with sustainable lives by making their journey enjoyable. All systems are designed to educate people to transform their lives. During the research, all of these conceptual, procedural, and sys tem artefacts are validated through publications, presentations and peer-review pro cesses. This thesis fills the gap in individual and family sustainability by bringing understand ing of human nature and systems together. Taken as a whole, it provides holistic un derstanding on sustainable life transformation and benefits researchers in both infor mation systems and sustainability. The thesis also lays the ground for future work in health and self-management, as it provides system solutions by synthesising core ideas from purposes of life and values, various human processes, and mechanisms to trans form our lives. At the practical level, the system architecture and the applications guide the system developers to design and implement systems for the sustainable transfor mation of individuals and families. Importantly, this thesis benefits individuals and families by making their sustainable life transformations holistic.