Mark out the area of your checkerboard on your painting surface.
Paint the area white. You can use colors other than white and black if you wish. Whatever colors you use, paint the area with the lighter color for this step.
Mark out a grid of squares, using the ruler and pencil, directly onto the painted area. Sketch it lightly.
Cut the masking tape into squares that match the width of the squares on your grid. If the tape width matches the square width, you can just measure off the matching length on the tape and cut it, using the utility knife. If not, you will have to trim the width of the tape. Cutting on a piece of scrap cardboard or a cutting mat will help protect home surfaces.
Apply the cut squares into your checkerboard grid, in alternating squares. The tape saves time. You won't have to painstakingly paint each edge of all the black squares.
Paint black paint into the exposed squares.
Wait for the paint to dry. Remove the tape.