True happiness doesn't come from wealth, success, or worldly achievements, but from recognizing our spiritual bankruptcy before God. Being poor in spirit means understanding that we have nothing to offer God and are completely dependent on His grace. Biblical figures like Moses, Gideon, and Isaiah exemplified this humility, recognizing their inadequacy before God's holiness. Jesus promises the kingdom of heaven to those who acknowledge their spiritual poverty. This isn't about low self-esteem, but about having a right understanding of who we are in relation to God's holiness and finding authentic contentment through complete dependence on Him.