As a trans-disciplinary approach to integrate a multi-disciplinary project (Yaoyorozu Project), we propose a concept of combination of systems technologies, that is, mathematical modeling of society, multi-agent simulation, and a scenario generation method. The objectives of the project are to design ubiquitous information society of 2010 and to extract issues of the future information society. This paper reports some research results of these systems technologies; a mathematical model relevant to the spreading of the ubiquitous information systems which consists of mobile/wearable devices and devices in environments, a social simulation focused on ubiquitous community sustainability, and a scenario-generating procedure for extracting future social issues. The synergetic relationship among these three technologies is also discussed.