Innovation is the buzzword today in organizations, with resources, time and effort being invested to innovate in order to gain competitive advantage. However, innovation, like other processes in organizational settings, takes place in a structured and planned way. This results in “organized innovation,” wherein the interplay of two opposing forces, namely, disrupting and organizing work at the same time, results in poor quality of innovation. On the other hand, consistent high-quality innovation is being done by individual innovators. We apply the transactional analysis framework to compare the process of innovation as adopted by the organizations vis-a-vis individual innovator using case research methodology. The chapter elucidates the individual and organizational processes by drawing similarities and differences between the two.