A flexible drill with a shaft having a nitinol portion (or nitinol region) provided between a stainless steel driver end and a stainless steel drill tip. The flexible drill with nitinol shaft is provided with a bearing surface to allow centering within a drill guide, low friction bearing and flexibility to drill around a curve. The bearing surface may be formed of a fluoropolymer such as LDPE (Low Density Polyethylene). The flexible drill shaft may be used through a drill guide, such as a curved drill sleeve.