It’s too easy to summarize the meaning of Job’s speech: He’s depressed. There is nothing to suggest moral failure. Some folks have come to visit Job in his distress and he’s about as entertaining as he can be, with truly grand imagery taken from the best of literary expression in his culture. This is what the reader needs to see. It’s nothing more than a very beautiful way of saying how bad he feels, and it’s entirely appropriate.
The first ten verses has him wishing he had not been born if this awful condition was his fate. The subtlety is rich. He wants to forget his birthday, particularly because the rejoicing was over such a healthy baby boy. He wished even God could forget that day. He calls for shadows and darkness to hide it from anyone else’s memory, too. Job personifies the day, hoping some horrific dark event would frighten it from showing its face. Let it be erased from the calendar. In the typical reckoning of a day consisting of first the night, then the day, he calls for the previous night to give no birth to the following daylight. Let the mythical great sea monster, Leviathan, be called up to devour the day before it can get started. More, let the day itself feel the same sense of doom and disappointment, passed over for its time in the sun; don’t even let it see its own morning stars. He’s angry that the day didn’t deny him his own birth.
For nine more verses Job wishes he had been stillborn, using rhetorical questions. Instead of suffering through consciousness, he could be asleep in the grave, the most common image of afterlife in that culture. He could share the grave with mighty kings who built great palaces, eager princes who amassed great wealth, as well as children born dead. There he would be among those who were unable to cause any more trouble, where their victims were also at rest. Both slave and master end up the same there. All of these are fairly common references used in daily conversation as a somber recognition of human limits.
The final verses are more rhetorical questions about God as mysterious and impossible to fathom at times. He doesn’t actually name God, but implies it with the divine “He”. Job first wonders aloud why God keeps him alive. We note Job respectfully waits for God’s permission to die. Just having the relief of the grave would be worth more than Job could express. His food is replaced with sighing and he drinks groaning all day long. He couldn’t imagine things being any worse. He can’t even escape into normal sleep.
So far, there is nothing improper here. Human sorrow is not a sin, and Job never indicates God is unjust. It’s a little long and windy, but not uncommon for talented speakers. It’s not yet a pity party in the social context of Job’s life.