The Midrash tells us that Pharoah had three advisers, Bilam, Yisro, and Iyov, from whom he sought counsel regarding his “Jewish problem.” Bilam advised Pharoah to kill the Jews. Yisro wanted no part of the plan and so he ran away. Iyov was silent.
Bilam was later punished mida k’neged midah by being killed by Bnei Yisrael. Yisro, who lost his wealth, his fame, his power as advisor to Pharoah, gained everything back midah k’neged midah by becoming the father-in-law of Moshe. But what of Iyov? Iyov figured that objecting at this moment would be a futile gesture; better to hold his tongue and live to fight another day, to intercede when he voice would be heard so he could perhaps mitigate the evil decree. Why was he punished with such severe suffering?
The Brisker Rav answers that Iyov was punished with suffering because when a person feels pain, there is usually little accomplished by crying in anguish, but a person cries anyway. When it hurts, you scream – you don’t make cheshbonos. Iyov may have had wonderful plans about when and how he should or should not intervene to help Klal Yisrael, but the very fact that he could sit there and make such calculations while other people’s lives were on the line showed a major character flaw. Sometimes you need to react, to scream, and leave the planning for later.
My wife suggested that the punishment of Iyov was deserved because he did not truly feel the pain of Bnei Yisrael; he did not relate to their experience. Therefore, he was made to suffer personally to bring the lesson home.