I have to admit; I always wondered what this part of Psalm 23 meant. Until a few years ago, I thought “He anoints my head with oil” was a figurative language for God keeping the Psalmist healthy. Here’s some of what I found written by Dr James Rasbeary:
My Prayer For You Today is that you would learn to wait on God for your answers. Not just waiting but wait expecting Him to answer at any time, and know that while you wait, He is there with you along the way. In doing this you will gain strength.