So many things Jesus said are paradoxical. They don't seem right, but they really are.
Like when he said the way to go up is to go down! If you want to sit at the head of the table, sit at the foot and maybe someone will recognize your value and move you to the front of the table. If you want to go up in the site of the Lord, humble yourselves before Him. If you want to be a leader in His kingdom, think of others before yourself and serve them.
Our natural way of looking at anything is usually just the opposite of what God desires, because we tend to be self-centered. And God wants us to become other-centered. The only way to do that well is first to be centered in your self, and in Him and in His wisdom. Because His way works.