The LORD is proud of Job's matchless virtue (1:8; 2:3). Job fears God and shuns evil. And even when calamity falls he does not sin by cursing God (1:22; 2:10). Instead, through all his laments and complaints, the LORD is still able to conclude in chapter 42 and verse 7 that His servant Job has spoken what is right.
And yet, in the verse immediately preceeding this Job has just said:
I despise myself and repent in dust and ashes. (Job 42:6)
Uh-oh, we think. Someone's got self-esteem issues!
But no. In fact Job hasn't been esteeming himself at all. He hasn't been contemplating himself. This is not the fruit of meditating on his sins or even on his sufferings. He hasn't been berating himself because he's a stupid, fat, ugly, unpopular, awkward, friendless failure. He hasn't had a thought about himself for four solid chapters.
Because for four solid chapters he has borne the brunt of the LORD speaking out of the tornado. Job's eyes have been dramatically lifted from himself and fixed on this Warrior Creator Commander called Yahweh. He has experienced the LORD's unanswerable wisdom in surround sound. And so in verse 5 Job summarizes exactly where his self-appraisal has come from:
5 My ears had heard of you but now my eyes have seen you. 6 Therefore I despise myself and repent in dust and ashes." (Job 42:5)
“I despise myself” says Job. By comparison with the LORD – upright Job falls flat on his face, confesses himself to be a sinner and says “I despise myself”. And that's a good and right and true and psychologically healthy thing to do. Not that Job wondered to himself "What would be the correct response to meeting my Maker?" It just came out. But as it came out it was extremely healthy.
Now there is a wrong despising of self. There is someone who is not looking at the LORD at all. Instead they look at themselves. They are self-absorbed and with their gaze fixed firmly on their belly-button they are despising themselves. We’ve all been there to some degree or another. And it’s wrong. But mainly it’s wrong for where the self-hater is looking. The object of their gaze is the issue - they must get their eyes off themselves. Then, when looking to Christ, a true appraisal of self will follow - they are (in Tim Keller's words) more wicked than they had ever realised but more loved than they had ever dreamed.
So there is a wrong despising of self - it's when you’re focussed on yourself.
But... there is a right despising of self – when you’re focussed on the LORD.
Isaiah has a similar experience. In Isaiah 6, he sees Jesus in the temple seated on the throne (cf John 12:30f), high and lifted up, the angels are calling out ‘Holy, Holy, Holy’, the temple is shaking, smoke is everywhere and Isaiah cries out:
5 "Woe to me! I am ruined! For I am a man of unclean lips, and I live among a people of unclean lips, and my eyes have seen the King, the LORD Almighty."
Isaiah wasn’t feeling particularly sinful that morning. He wasn't running through a list of his prior misdemeanors. No-one was reminding him of past sins. Isaiah felt no guilt at all that morning... until he saw the King. Then he said “Woe to me, I’m ruined!”
Or think of Peter fishing with Jesus in Luke chapter 5. He’s in the boat with the LORD of Isaiah chapter 6. And they have a miraculous catch of fish. And Luke 5 verse 5 says:
When Simon Peter saw this, he fell at Jesus' knees and said, "Go away from me, Lord; I am a sinful man!"
Peter confesses to being a sinner when he sees the glory of Jesus. Peter hasn’t just remembered some sins from his murky past. He’s not even thinking about his sins, he is simply looking at Jesus and saying “I do not match up.”
Of course the ultimate place to look to find a true estimation of yourself is to Christ crucified. That's the sinner's fate. And that was your death - you died with Christ, the old man crucified. You will never be able to feel your way towards this verdict. Preachers, no matter how keenly they focus on individual sins you've committed, can't whip up this sentiment. And turning to yourself in order to work it up is itself sinful. Instead I look to the LORD high and lifted up (Isaiah 6:1 <=> 52:13). I allow the cross to be God's verdict on me. I am co-crucified with Christ and therefore reject the old self completely. And yet
I have been crucified with Christ and I no longer live, but Christ lives in me. The life I live in the body, I live by faith in the Son of God, who loved me and gave himself for me. (Gal 2:20)
The true and right self-hatred is fundamentally to allow the cross to be God's verdict on the old you. And your true and right self-appreciation is not gained by trusting in the new you. No, the life you live in the flesh you live by faith in the Son of God. Trust His love for you shown decisively right when you were most hateful.