I would make a small jig that had two perpendicular holes one to guide the
drill, and the other to index the next hole.
The jig should have a shoulder to space it properly from the edge of the
The way I would approach this would be to start with a block of wood larger
than needed and drill the two holes straight through. When the holes are
drilled make sure they are perpendicular to each other and properly spaced.
Once you have confirmed this, now cut the block at an angle. Now you can
conform the outside of the block to the size you want and add a fence.
With this done you can clamp the jig to the your board, place a piece of
tape on your bit to mark the depth, and drill your first hole. After the
first hole is drilled, insert a pin or a wood dowel into the other hole and
insert the pin into the first hole in your board. This will assure nice
even spacing and the proper angle.
Some points to consider. A brad point will probably work better than a V
point. This jig will self destruct over time. How much time depends on how
careful you are in holding the drill to avoid chewing up the guide.
Drilling a little and cleaning out chips will help the jig to last long
enough to finish.
Making a second jig using the first to gage the holes and the angle might be
the first holes you drill with the jig in case you wear the first jig too
The thicker you make the jig the more accurate it will be.
If you have a drill press, you might want to make a different king of jig.
Use a piece of pegboard clamped to your table. Also attach a fence. If the
holes in the pegboard are at the spacing you want this is easy to attach the
fence square to the peg board and use a peg to stop your board. If you need
a different spacing then setting the fence at an angle to the peg board will
allow you to shorten the distance between holes.
Either of these should give you a better result than measuring and
attempting to drill at an angle.
About the time I had mastered getting the toothpaste back in the tube, then
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