First in the field of blesseds according to Jesus is being "poor in spirit." It is a unique way to start a sermon, and certainly not an easy sell to a worldling who (thinks he) wants blessing. Previously we considered the second in the list, namely, that mourning is a blessing that includes the promise of comfort. As one example, Paul called the Corinthians to mourn over sin in their midst (1 Corinthians 5:2). They likewise would have been benefited by planting this tree in their soul: humility (1 Corinthians 5:6).
"Blessed are the poor in spirit, for theirs is the kingdom of heaven." Again I want to argue that the happiness is not just in the future, or in the grasp of the future now by faith. There is blessing coming later (a kingdom), there is blessing in the current knowledge of what is coming (hope), but it is blessing to have a proper view of one's self.
Humility is a blessing because self-exaltation turns out to be really hard. It is a discouraging work to hunt for reasons to praise something or someone (like oneself) that isn't so great, let alone to lobby a group to pretend there is greatness. Most pride has the unfortunate position of not fitting with reality, and even friends have limits for credible imagination.
Humility is also a blessing because it hurts less to be corrected. We sin, or we make mistakes, and pride multiplies the original problem: it makes us defensive and distanciung, and it makes the fall farther when the strike hits. A humble person is already low; you can’t crash to the floor when you’re already on it.
And humility is a blessing because it shuts the gate to a number of other sins. Pride is what provokes anger (“How dare you not praise me!"), bitterness (“Why don't you recognize me?"), envy ("I deserve to have that."), and slander (“They do not deserve to have that!").
Jesus promises the heavenly kingdom to the humble, and the humbled are blessed in the humility itself.