A smart self-driving system includes a body, such as a piece of luggage, supported by a plurality of wheel assemblies. One or more front proximity sensors are coupled to the body and configured to detect an object moving in a given direction while the body is in a rear follow position behind the object. One or more side proximity sensors are coupled to the body and configured to detect the object moving in the given direction while the body is in a side follow position on the side of the object.