"How blessed is the man who does not walk in the counsel of the wicked, nor stand in the path of sinners, nor sit in the seat of scoffers!" (Psalm 1:1). This verse gives three characteristics of a blessed man; each one involves deliberate disassociation from ungodly people. First, he does not walk with the wicked - those who are guilty of crimes against man or God, those who are hostile to God. The blessed man's feet do not travel the same paths with such people; he does not desire to walk in the same direction. Second, the blessed man does not stand with sinners - those who have been condemned and judged as offenders. He does not take his position with such people or accompany them. Third, he does not sit with scoffers - those who deliberately disfigure their faces as they speak from hearts of ridicule.
Throughout life, the blessed man will have to come in contact with these people from time to time, but he is not habitually with them. He does not order his life so that he is known for regular association and companionship with them. Instead, he wants to associate with God and His Word (v. 2). This is not a casual acquaintance, like those other relationships could be; rather, it is as constant as possible. Day and night the blessed man seeks the Word because he delights in it. Those other associations might be inevitable in the course of life, but this one is deliberate, based on a conscious choice to avoid associations of defilement and evil, and to embrace associations of righteousness and godliness.
"How blessed is he whose transgression is forgiven, whose sin is covered!" (Psalm 32:1). David wrote this psalm from experience, knowing in a powerful way what is was like to have his sin forgiven. Prior to that forgiveness, David was not blessed. Rather, he experienced his body wasting away, constant groaning, God's hand heavy on him, and his strength drained away as from an illness. Once his sin was forgiven, that oppressive situation changed; David defines that change and restoration as blessing.
This verse is very personal. David is talking about specific sin and specific forgiveness, indicating that the blessing is renewed each time such confession and forgiveness takes place. Forgiveness refers to something being lifted and carried off; there is blessing in having such a heavy burden removed. David also says his sin is covered - hidden, clothed, or concealed so that the nastiness is no longer seen. There is blessing in not having a constant visible reminder of that stain. David's emphasis regarding blessing is on having the negative and oppressive removed. He doesn't specifically describe blessing from a positive standpoint, although in the final verse he speaks of gladness, rejoicing, and shouting for joy.
"How blessed is the man to whom the LORD does not impute iniquity, and in whose spirit there is no deceit!" (Psalm 32:2). Instead of continuing to refer to a specific personal incident, the next verse in the same psalm describes an overall principle. This more general statement gives two descriptions of a blessed man. First, he is one to whom God does not impute iniquity. There would not be blessing in knowing there is something unpaid and heavy that is hanging over one unresolved. It would be a blessing, however, to have the ledger cleared and balanced, not caught in a position where God has something to hold on one's account. Second, the blessed man is someone in whose spirit there is no deceit. In a broad sense, deceit is overlooking or taking something casually, probably deliberately trying to hide it. In the context of sin, it is someone who carries un-confessed sin, particularly with the attitude that it isn't a big deal or for the purpose of trying to make himself look good. Blessing comes to those who don't try to deceive, but who acknowledge and deal with sin.
"Blessed is the man whom You chasten, O LORD, and whom You teach out of Your law" (Psalm 94:12). There are wicked people who face God's judgment without ever falling under His favor; there are others who experience correction because an interested God chooses to intervene in their lives. This psalm contrasts those two groups, and identifies the second group as blessed. God first of all chastens these blessed people. He disciplines, instructs, admonishes, and corrects. This chastening, while not necessarily harsh, is deliberate; the goal is to correct what is wrong so the recipient will change and do what is right. A loving parent does this because he wants his child to turn out well, not facing harsh consequences for wrong choices; he desires long-term good and benefit for his child. When God does this for His children, they are blessed. A loving and benevolent God is trying to keep them on the right path and prevent the heavy repercussions of following the wrong path.
God's second action is to teach these blessed people from His law. This training requires some effort by the students to learn. Again, this is a personal intervention by God to help these people know the right way to walk, a way that will lead to blessing, and not to destruction or burden. God's instruction about the right way is found in the Bible. Those who diligently study and follow the Bible will know the right way to live so their lives can be blessed.
In summary, the blessed man avoids the lifestyle and associations with sin. He confesses known sin and yields to God's correction. He deliberately studies the Bible so he can avoid sin.