The blessedness of which the psalm speaks does not mean that we will be materially/financially prosperous. It may actually be the contrary; exactly because of the role the wicked plays in the church. The blessedness promised is the divine presence in the life of the true believer, even when there will be times of suffering.
1 Blessed is the man who walks not in the counsel of the wicked, nor stands in the way of sinners, nor sits in the seat of scoffers;