Designing socio-technical systems like IT-supported teaching-learning systems that motivate learners while at the same time stimulating knowledge transfer has become challenging. Teaching-learning techniques that consist of a social context that interacts with and is supported by information technologies are often bundled in a holistic design artifact. To explore a socio-technical design artifact, one must recognize that it consists of several sub-artifacts, each of which must have its own design approach. We introduce the research approach of designing and piloting the IT-supported teaching-learning concept, sensitized to the demand of distinguishing among several socio-technical sub-artifacts. We present the purpose of our design science research (DSR) journey and differentiate among several design artifacts, each of which make prescriptive knowledge contributions and, thus, represent diverse types of theory in information systems. The first artifact is a Peer Creation Process for enhancing knowledge transfer and documentation, which contributes to a nascent design theory. The second artifact is a User-Centered Process to gamify LMSs, which contributes to a theory of design and action. We describe the DSR journey that was part of the project StaySmart, the purpose of which was to design and evaluate a teaching-learning concept for knowledge workers. Teaching-learning artifacts usually have one purpose: to design and evaluate the learning experience. However, designing such artifacts requires identifying their sub-purposes, which leads to designing and evaluating several design artifacts, which we call teaching-learning techniques, so a holistic design artifact usually has several design artifacts. Therefore, the project makes distinct prescriptive knowledge contributions and has the potential to create distinct types of theory in information systems. Our case provides guidance in developing artifacts for a holistic design artifact and in understanding how such artifacts can be separated into sub-artifacts that have their own design science approaches.