Soft-tipped pole designs and methods for their use on pavement are disclosed. The soft, gripping pole tip can slow down a roller skier or skateboarder by slowing down the rider directly and by providing increased rider stability during breaking. This is accomplished by the rider pressing one or two pole tips against the pavement, with or without the use of a fulcrum point for increased leverage. The soft rubberlike tip has a large surface area that provides durability as well as variable levels of frictional force imparted against the pavement. The fulcrum for the pole can be the user's arm or leg as well as fulcrum element fastened to the rolling device.