A flexible drill and method of drilling a material are disclosed. According to one embodiment, a flexible drill includes a lower sub-assembly connected to an upper sub-assembly, where the lower sub-assembly comprises a retainer tube and the upper sub-assembly comprises a guiding tube; a drilling tip, and capable of orienting the drilling tip at a predetermined position after accessing a material to he drilled through a substantially straight passage having a lone axis. The predetermined position is at least 10.degree. off of the lone axis of the substantially straight passage. According to one embodiment, a method of drilling a material includes the steps of (a) providing a flexible drill; (b) advancing the drill through a substantially straight passage until the drilling tip accesses the material to be drilled, thereby orienting the drilling tip at the predetermined position; and (c) actuating the drill.