How can I drill holes less than 1" from a wall?

Question

I need to drill pilot holes through 1x1 and into a stud, with the 1x1 flush with the wall. I figure the hole has to be no more than 5/8" from the wall. My drill is too wide to drill a perpendicular hole that close to the wall.
For reference, this is a follow up to a different question Can I safely hang pegboard between studs, rather than across them?, where a user recommended I attach 1x1 to the studs. I didn't think of it at the time,  but the closest my drill bit can get to the wall while remaining perpendicular to the 1x1 and stud is a little over an inch.
I tried Googling, but that kept bringing me to right angle adapters and flexible extenders - but every time I looked at one, they were clearly meant for driving, not for drilling. They also seemed focused on solving the problem of having insufficient space between the drilling surface and some other parallel obstruction, not the distance from the desired hole to a plane perpendicular to the drilling surface - because they don't give a specification for the diameter of the chuck and its clearance from the top edge of the tool.
How do I drill a hole that close to the wall?

Ecnerwal · Answer

Various methods, the most accessible of which tends to be a long drill bit - 12-18" long, allowing the chuck to get out of the way.
If you don't flex the bit, the slight angle (not quite perpendicular) is generally not a problem, but under the guise of "aircraft drills" there are very long bits with short flutes and a long smooth shank that flex sufficiently that you can get them perpendicular, if needed.
A physically smaller drill chuck is the more obvious but generally less accessible method.

Solar Mike · Answer

Another possibility is to drill out a 2” or 3” plug, then drill that plug with the 1” hole off centre. Then you can position the plug back in the original hole with the 1” hole as close to the edge as you wish, glue into place and fill to finish.

Answered by Solar Mike on February 2, 2021

bobflux · Answer

For small, not too deep pilot holes, you can just use a nail instead of a drill bit. Hammer it in and pull it out. The "pulling it out" part is the reason why it'll only work if the hole isn't too deep.
I've also used Torx bit screws to make this kind of annoying pilot hole. With a bit of care, the torx bit will work even at a slight angle, especially with an extender. It's a bit fiddly so the screw has to be hammered in the right place to make sure it doesn't walk or slip.
There is of course a proper tool to extend a hex drill bit to go into hard to reach places:

This is more practical than carrying a set of 30cm drill bits, and it'll work with the small diameter bits too. If you pile up enough extenders, the assembly has enough flex to drill or screw right up to the wall without hitting it with the chuck... and it's still rigid enough to be controllable.
...or you could use screws that don't need pilot holes.

How can I drill holes less than 1" from a wall?

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