Abstract: The invention is directed to a telescoping pole to help direct a longboard comprising a first and second portion. The first portion includes a first end, a second end and a first tubular shaft. A first handle is positioned at the first end, while a second handle is positioned along the first tubular shaft between the first and second end. The second portion also has first end, a second end, and a second tubular shaft (having a diameter less than the first tubular shaft). The first end of the second portion is attached to the first portion through a first coiled spring. A wheel assembly having a spinning wheel is affixed to the second end of the second portion having a third tubular shaft having diameter less than the second tubular shaft. A second coiled spring is placed over the third tubular shaft, which engages the second portion.