A system and method for optimizing a drilling operation is provided. The system has a drilling a drilling operation optimization unit. The drilling operation optimization unit has a base model unit for producing a base model of the reservoir and a reservoir stress unit for producing a three dimensional stress model of the reservoir. The drilling operation optimization unit has a trajectory unit for determining at least one property for at least one wellbore trajectory based on the base model and the three dimensional stress model, wherein each of the wellbore trajectories is selectable by an operator. The system has an operator station for inputting data into the drilling operation optimization unit at the wellsite and a drilling tool for forming a wellbore along at least one of the at least one selected wellbore trajectories.