“You anoint my head with oil; my cup runs over.”
Psalm 23:5b (NKJV)
In Bible times, shepherds would anoint their sheep by pouring oil on their heads. This is because lice and other insects would try to burrow their way into the sheep’s ears, which could eventually kill the sheep. Anointing the sheep’s head would make the wool slippery, causing the insects to slide off and saving the sheep’s life.
When the Bible speaks about ‘anointing’, it often signifies protection, blessing and empowerment. Anointing is also representative of the Holy Spirit, and speaks of His influence on us. The “head” is symbolic of leadership. Your head is like your control room; it’s where your brain is (to make decisions) and it’s where your eyes are (for vision; looking forward).
“You anoint my head with oil; my cup runs over.”
Psalm 23:5b (NKJV)
God blesses and protects you by empowering your control room (your thinking and decision-making, and your vision) with His Holy Spirit. The Holy Spirit empowers you with divine (godly) wisdom and insight to make good decisions which will protect you and bless you.
“When the Spirit of truth comes, he will guide you into all the truth, for he will not speak on his own authority, but whatever he hears he will speak, and he will declare to you the things that are to come.”
John 16:13 (ESV)
The Holy Spirit guides us into all truth; He doesn’t push us into truth. He guides - but we need to be attentive to His leading and we need to choose to follow. And when we follow His leading (His divine wisdom) it will result in protection and blessing.
“My cup runs over” speaks of abundance, excess and prosperity. Because of what Jesus did for you, you have this blessing and provision in all its fullness. It’s yours. But experiencing this blessing isn’t automatic in our lives; we receive it by faith, which is expressed by trusting God enough to follow His leading. God is not the God of enough; He is the God of more than enough. He doesn’t want to just give you enough to satisfy your needs, He wants to bless you so that you can be a blessing (Genesis 12:2). His will for you is that you prosper and be in good health (3 John 2). He is a good Father who wants good things for you.