A drill guide that includes associated components and various methods of use herein. The drill guide includes a first guide column and a second guide column provided on a base plate. The drill guide also includes a chuck carrier adapted to operatively receive a drill chuck of a portable drill. The chuck carrier is operably engaged with the first guide column and the second guide column, and the chuck carrier is linearly moveable along the first guide column and the second guide column between a return position and a plunging position relative to the base plate. The drill guide also includes a tapered portion defined in the first guide column. The drill guide also includes a depth stopper that is operably engaged with the first guide column, wherein the tapered portion enables self-tightening of the depth stopper about the first guide column.