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So what does being "blessed" really mean? In Deuteronomy 28, blessings are given for obeying the Lord your God. In Matthew 5 (The Beatitudes), God blesses those who are poor, mourn, humble, merciful, persecuted for doing right, those who hunger and thirst for justice, those who work for peace, those whose hearts are pure.
For me, being blessed comes down to being at peace with my decisions and my life. And that happens when I obey the Lord my God. It happens when I live within God's boundaries for my life. It happens when I ask for God's blessing as I am in agony at the pain a family is feeling when facing the death of a loved one. It happens when my life is easy and carefree... and when my life is filled with anguish.
When I think about my "blessedness," it's about feeling the touch of God, knowing the peace that surpasses all understanding. It's not about winning the game, making a lot of money, or any other circumstance. It's the peace within the circumstances, whatever they are.
God bless you.