The idea is good. It would take a heck of a drill or you may never get it out. Reminds me of when I was blasting my water line. I was using a 2" impact drill to drill blasting holes. I was using a SPS 30" drill bit. Got the bit stuck in the rock. I could not get it out. I decided to blast, thinking the rock would crack and I would find the bit laying on the ground. I never found that bit. That bit cost $100 - 30 years ago.
Remember the old 1/2 in drills. That may be what would be needed - if oak. Best Wishes, Larry