When you are encouraging someone, are you discouraging them? 

When does this happen? When you think carnally and not spiritually.

Naomi thought she was encouraging Orpah and Ruth by asking them to go back to heathen Moab when the women desired to move to Godly Bethlehem with her. 

Ruth wanted to grow in Godly faith, and moving to Bethlehem, the city of the living God, was the best choice. But Naomi was getting all (carnal) emotional, thinking from a fleshly point of view. Naomi should have encouraged them to know the living God. (Ruth 1)

Encourage children according to the Word, not your feelings.

Many parents end up wrongly encouraging their children because of feelings or fears they have in their hearts. This type of encouragement does great harm to the child spiritually. He, or she, grows up spiritually stunted. 

Some parents discourage their children from talking to spiritual believers because they fear their children may decide to take up a future in ministry. These parents have already decided what they want for their children without bothering to seek God. A parent must walk by faith, leaning on God in prayer and supplication for God's will for their children.

Who will take care of us when we are older? A question that plagues their heart as they grow weary in life. Fear torments them, and many believers live in the torment of unbelief for themselves and their children. It is sad to watch how some parents cripple their children's spiritual walk. But God does His business and creates a way for these children from believing families who get lost.

Not all encouraging is necessarily encouragement. Study what the Word of God says about this life in Christ. As long as we are in the flesh, the devil will manipulate us back into thinking and speaking like the old nature of a man born of the flesh.

Rinse your heart with God's Word daily. Maranatha, Praise God, and Amen.