What does Proverbs 21:29 mean?
ESV: A wicked man puts on a bold face, but the upright gives thought to his ways.
NIV: The wicked put up a bold front, but the upright give thought to their ways.
NASB: A wicked person displays a bold face, But as for the upright, he makes his way sure.
CSB: A wicked person puts on a bold face, but the upright one considers his way.
NLT: The wicked bluff their way through, but the virtuous think before they act.
KJV: A wicked man hardeneth his face: but as for the upright, he directeth his way.
NKJV: A wicked man hardens his face, But as for the upright, he establishes his way.
Verse Commentary:
This proverb repeats earlier condemnation of arrogance and unwillingness to learn. The "bold face" noted here is when someone ignores advice or correction, acting as if they are still right (Proverbs 21:24). It can also imply someone using deception and bluster to convince other people of lies. Either way, a godly person is willing to hear advice (Proverbs 12:15), and to change his mind when it's the sensible response (Proverbs 19:20).

Stubbornness is its own form of sinful pride (Proverbs 29:1). Solomon's imagery here is of a person scowling or twisting up their face, like a child who refuses to be told "no." Such a person resists correction. When told to repent and believe, he hardens his heart. He tries to gain others' trust by putting on a hypocritical face that hides his deception. The upright person is more self-reflective, carefully considering what he does. The godly man submits to the Lord. He repents when he is wrong and seeks forgiveness. He relates to others honestly and humbly.

The Pharisees practiced deception. Jesus said they were hypocrites (Matthew 23:13). They appeared to be religious, but they were wolves in sheep's clothing. They appeared to be as clean on the outside, but in their hearts were full of rot and death, like painted tombs (Matthew 23:27–28). At one time the young man Saul of Tarsus was a Pharisee, and he agreed with the murder of Stephen (Acts 7:59—8:1), but the Lord changed Saul's heart, and Saul became a submissive servant of the Lord (Acts 9:1–6).
Verse Context:
Proverbs 21:17–31 continues the recorded wisdom of Solomon (Proverbs 10:1). He contrasts the wise person with the foolish person, the righteous with the wicked, the lazy person with the diligent, and human wisdom with the Lord's sovereignty.
Chapter Summary:
This chapter begins and ends with a declaration of God's sovereignty. He alone judges the heart; the Lord considers intentions just as important as physical actions. Other comments include statements about unpleasant spouses, proper perspectives on wealth, work ethic, and the essential nature of godly wisdom. Human wisdom is no match for the sovereign Lord, who alone is ultimately responsible for victory in battle.
Chapter Context:
This is part of the second major section of the book (Proverbs 10—22) featuring nearly four hundred statements. Most of these are two-line comments presenting common sense and general wisdom. The vague theme of chapter 21 is God's control. Man may believe he is in control of his circumstances, but God superintends everything. The chapter begins and ends by assuring the readers that God holds ultimate sway over all things.
Book Summary:
Proverbs is best understood in context with the books of Ecclesiastes and Job. In Proverbs, “wisdom” is given in short, simple, general terms. Ecclesiastes represents wisdom based on observation and experience. This often shows how the general principles of the book of Proverbs don’t apply in absolutely every circumstance. Job represents wisdom based on the experience of suffering and injustice. All three come to the conclusion that God does indeed know best, and the most sensible course of action is to follow His will.
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