Nowadays, progress is constant and inherent to a living society. This may occur in different arenas, namely in mathematical evaluation and healthcare. Assistive technologies are a topic under this evolution, being extremely important in helping users with diminished capabilities (physical, sensory, intellectual). These technologies assist people in tasks that were difficult or impossible to execute. A common diminished task is orientation, which is crucial for the user autonomy. The adaptation to such technologies should require the minimum effort possible in order to enable the person to use devices that convey assistive functionalities. There are several solutions that help a human being to travel between two different locations, however their authors are essentially concerned with the guidance method, giving special attention to the user interface. The CogHelper system aims to overcome these systems by applying a framework of Speculative Computation, which adds a prediction feature for the next user movement giving an anticipation ability to the system. Thus, an alert is triggered before the user turn towards an incorrect path. The travelling path is also adjusted to the user preferences through a trajectory mining module.