I wonder what went through the minds of Jesus’ disciples when Jesus shared this beatitude. For these collection of truths, which we know as the Beatitudes from Jesus’ Sermon on the Mount, seems to go against society’s way of thinking and living. Jesus, however, was not directing these teachings to the general population, but rather to His closest friends. His teaching aims to prepare His followers for His kingdom. Living out these truths will result in a lifestyle radically different from the world’s.

We usually attribute “blessed” to someone who has acquired wealth, good health, power, or prestige. But Jesus challenges our thinking as He calls some people “blessed” who appear quite the opposite. How exactly is the person who mourns blessed? Mourning seems to depict images of funerals and suffering. It’s not a natural thing to view oneself as blessed when struggling, resulting in a bucket of tears, red puffy eyes, and a burdened heart.

Although blessed usually means “happy” in the Bible, the context of Matthew 5 seems to convey more of “an enviable state”. Jesus is distinguishing the world’s image of happiness with true blessedness—spiritual riches—which only comes from a right relationship with God.

GotQuestons.org notes: The term mourn means “to experience deep grief.” In keeping with His theme of spiritual blessedness, Jesus seems to indicate that this mourning is due to grief over sin. The people who agree with God about the evil of their own hearts can attain an “enviable state of blessedness,” due to the comfort they receive from communion with the Holy Spirit.

Jesus called the Holy Spirit the Comforter (John 14:16, 26; 15:26; 2 Corinthians 1:4). The Spirit comforts those who are honest about their own sin and humble enough to ask for forgiveness and healing. Deep repentance requires deep conviction that comes from deep brokenness. Those who hide their sin or try to justify it before God can never know the comfort that comes from a pure heart, as Jesus talks about in Matthew 5:8 (cf. Proverbs 28:13; Isaiah 57:15). This is the difference between godly sorrow and worldly sorrow.