A system and method to facilitate the drilling of one or more lateral wellbores while eliminating one or more trips downhole. The system utilizes a drilling assembly comprising an impregnated drill bit or other suitable drill bit. The impregnated drill bit is coupled to a whipstock by a connector for deployment downhole in a single trip. The connector comprises a separation device which facilitates disconnection of the impregnated drill bit from the whipstock once the whipstock is anchored at a desired downhole location.