Jesus now focuses on the disciples, initially the twelve, but then also the larger group. The former are ordained to be citizens of God’s kingdom, and it is Jesus’ intention that the crowds also move in this direction (see Luke 7:1). Jesus presents the listeners with the choice of being blessed or falling under the woe. He does not address two groups, but tells the disciples and those listening when someone is to be praised and when someone falls under the woe. This can be seen from Luke 6:22 read in conjunction with Luke 6:26, for these verses are not about two kinds of people, but concern the one listener who must choose from two options. In other words, you can ensure that Luke 6:22 is about you, but if you do not then Luke 6:26 will apply. Jesus certainly also here warns preachers about the trap of wanting to please people!
Blessed means to be congratulated for the state you are in, because it pleases God and as a result he blesses you.