Paul was truly broken in Romans 9...
Romans 9:1 I speak the truth in Christ—I am not lying, my conscience confirms it in the Holy Spirit— 2 I have great sorrow and unceasing anguish in my heart. 3 For I could wish that I myself were cursed and cut off from Christ for the sake of my brothers, those of my own race, 4 the people of Israel.
Did you hear that? A Penn paraphrase would sound something like this:
When is the last time you were broken? Lord, help us to mourn.
"I'm serious about this - God knows how serious I am - I am broken. -B-R-O-K-E-N-
If by going to Hell, my brothers could know Chirst - I would go. I want them to know Him. They must know Him!"
If you want to read more about this passage check out "Damned for the Beloved" from DesiringGod.org