Psalm 23:4 assures you that when you feel your world is falling apart you are not alone. Your Shepherd is with you and will comfort you in the midst of your seemingly hopeless predicament.
Verse 5 continues the psalmist’s personal testimony. When he felt like everyone was against him, like a sheep surrounded by angry wolves, his shepherd was there preparing a banquet table before him. Instead of being the meal for the wolves they stood there perplexed while he enjoyed the meal prepared for him.
Again notice the psalmist speaking to his shepherd in awe, “You prepare a table before me in the presence of my enemies.” If you keep your eyes on your enemies who are present you will have a hard time enjoying the banquet prepared and set before you. But if you fix your eyes on your shepherd, His presence dispels the fear and frees you to enjoy the meal prepared for you. It will nourish you so you will be able to overcome your enemies.
Another special touch of the shepherd’s favor; he anoints your head with oil. The Bible Knowledge Commentary explains, “The image of anointing the head with oil, which was refreshing and soothing, harmonizes with the concept of a gracious host welcoming someone into his home. In view of the table and the oil David knew that his lot in life (his cup) was abundant blessing from the Lord.”
The idea of the cup overflowing suggests that when you’re in a relationship with the Lord where He can bless you, that blessing will overflow and begin touching the lives of others for their good, maybe even your enemies.