What does Isaiah 5:21 mean?
ESV: Woe to those who are wise in their own eyes, and shrewd in their own sight!
NIV: Woe to those who are wise in their own eyes and clever in their own sight.
NASB: Woe to those who are wise in their own eyes And clever in their own sight!
CSB: Woe to those who consider themselves wise and judge themselves clever.
NLT: What sorrow for those who are wise in their own eyes and think themselves so clever.
KJV: Woe unto them that are wise in their own eyes, and prudent in their own sight!
NKJV: Woe to those who are wise in their own eyes, And prudent in their own sight!
Verse Commentary:
Isaiah next declares "woe" to those who are arrogant about their own understanding. This verse fits the pattern of the proverbs of Solomon. The people in Jerusalem and Judah had fallen into a common human trap: wanting to be the source of all the goodness in their own lives, including all knowledge. Sin often convinces us that if we don't like something, or cannot fully understand it, it must be wrong. That makes us the ultimate judge of good and evil (Isaiah 5:20) and ignores our own weaknesses (Isaiah 55:8–9).

Solomon's proverbs repeatedly emphasize that true wisdom and knowledge begins with the fear of the Lord (Proverbs 1:7, 9:10). When Proverbs uses the word "fear" here this is more of an understanding of power and greatness of God. It is to be in awe of something. An example could be to fear the ocean because you understand its power and unfathomable size. Yet you still are in awe of its beauty and power. The idea isn't to cower in terror, but to act with good sense and respect. Wise "fear of the Lord" means recognizing God is only true and trustworthy source of understanding about how life works best (Proverbs 8:32–36). In fact, He's the ultimate authority on how we ourselves work best. He knows us better than we know us.

People who have God's wisdom use His Word as the standard against which all other ideas are judged. If it disagrees with His revelation, it is wrong. Our hearts desperately want to find the answers ourselves, but we always need to come back to that ruling standard of God's wisdom in the Scriptures (Proverbs 4:10; Psalm 119:81; 1 Corinthians 4:6; 2 Timothy 3:16).
Verse Context:
Isaiah 5:8–30 contains Isaiah's dire predictions about the upcoming judgment of Israel. The first "woes" are to the greedy and the pleasure-seeking drinkers. They will go into exile and to the grave for refusing to acknowledge God. The Lord then will be exalted for restoring justice and righteousness. The next woes are to those who embrace sin and mock the coming judgment. These are also those people who have mixed evil and good and believe they know better than God. The final listed woes are those who make it a point of pride how much alcohol they can drink, as well as how they can work the system with bribes. The Lord will summon the armies of the nations to bring judgment on His people.
Chapter Summary:
Isaiah 5 begins with a parable about a farmer who builds a vineyard that produces sour grapes. The owner says he will lay waste to the vineyard. Isaiah reveals the owner to be the Lord and the vineyard to be Israel. Israel's bad fruit includes the greed of the wealthy and the hedonism of the people. They will go hungry and thirsty, into exile, and the grave. The Lord will be exalted for His righteousness. Isaiah pronounces woe on the sinners, the mockers, and the unjust rulers. The Lord will summon the nations to judge His people.
Chapter Context:
Early chapters (Isaiah 1—4) established a prophetic message given to the people of Israel. Isaiah 5 begins a new section with a parable about a vineyard that produces wild grapes despite all the work the owner has done. The vineyard is Israel, and the owner is the Lord. He will lay waste to the vineyard for the greed and drunkenness of the people. They will go into exile and the grave. The Lord will be exalted, but woe to those who embrace sin, and mock God's judgment. As well as those who take bribes against the poor. He has summoned the nations. Judgment is coming. The next chapter includes one of the Bible's most famous visions (Isaiah 6).
Book Summary:
Isaiah is among the most important prophetic books in the entire Bible. The first segment details God's impending judgment against ancient peoples for sin and idolatry (Isaiah 1—35). The second part of Isaiah briefly explains a failed assault on Jerusalem during the rule of Hezekiah (Isaiah 36—39). The final chapters predict Israel's rescue from Babylonian captivity (Isaiah 40—48), the promised Messiah (Isaiah 49—57), and the final glory of Jerusalem and God's people (Isaiah 58—66).
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