The importance of promoting self-medication is increasing, and the active participation of pharmacies is required to support this. We developed a training program based on the Attention, Relevance, Confidence, and Satisfaction (ARCS) model, which is a motivational design process to train pharmacists who support the proper use of OTC drugs, and for insurance pharmacists who usually perform dispensing work. In the six months of training, we conducted six sessions for insurance pharmacists on the subject of colds and constipation. In addition to conducting lectures and exercises on OTC drugs, we provided pharmacists with an opportunity to practice the training content during their daily work, and discuss solutions to the problems that they encountered. Of the eight participants who attended all workshops and were part of the final evaluation, seven provided OTC drugs after considering whether it was necessary to provide them. A total of six advised patients who came to the pharmacy to have their prescription medications dispensed that there were OTC medications that they should be careful about taking. These results suggest the usefulness of this training program based on the ARCS motivational design model.