The aging issue in the work context is becoming a significant element of the future sustainability of service and industrial companies. It is well known that with increasing worker age the problem of maintaining the performance and the safety level when fatigue increases is a crucial point, and fatigue increases with the age. Due to social and political developments, especially in Western countries, the retirement age is increasing and companies operate with a higher workforce mean age. Therefore, the problem of recognizing and measuring fatigue has become a key aspect in the management of aging. Note that in the scientific engineering field, the problem of fatigue evaluation when a worker is performing his/her work activities is an important issue in the industrial and service world and especially in the context of the researchers that are investigating the human reliability assessment. As it is clear from the literature, the industrial operations management are suffering from some misleading concepts that only the medicine scientific context can clarify. Therefore, the aim of this paper is to define what are the open issues and the misleading concepts present in the classical fatigue evaluation methods, and second to define two experimental curves of fatigue that will help the decision makers to minimize the impact of fatigue on the workers, thus maximizing the sustainability of the working tasks assigned. This aim is achieved by examining the medical literature about the measurement of a particular kind of fatigue related to the circadian cycle, i.e., the cognitive one; after that, a survey about the possible technologies for measurements is performed. On the basis of technology selection, an experiment on real work activities is performed and some remarkable results about the fatigue in the workers observed and the technology use and its limitations are defined.