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Jamie said:

Confidence in one's own salvation is rather a dangerous thing - and a very protestant thing."

Raoul76 said:

"I'm feeling pretty confident now that I have the right approach to the crisis, and that God has given me a chance to be saved, --"

This is not confidence in my salvation.  The confidence is that I have the right approach, but in a time like this, confidence in salvation would be borderline insane.  For all I know, God has abandoned us all, and it sometimes feels like that to me.  But I try not to despair because it's a sin.  My fear and trembling are beyond description but I don't wallow in it publicly.  If I gave into it, I would crumble.

I'm actually worried because I'm becoming a little bit "hard."  When I first became Catholic I could not accept the notion that I might go to hell.  Now sometimes I have dark, fatalistic moments, almost masochistic, where I think "You're doomed, just give into it."  I know, of course, this is a temptation.

I have many problems in my life besides figuring out the right theological position or keeping the dogmas together.  Many moral problems that may take me down.  I don't mean sins, but for instance, I'm living off family money that is kind of dirty -- we wouldn't have it if we were Catholic all along.  If I can't get a job, will I have the strength to leave it all behind and be homeless?  Is that what God wants from me?  These are the questions that torment me.

I have many problems in my life besides figuring out the right theological position or keeping the dogmas together.  Many moral problems that may take me down.  I don't mean sins, but for instance, I'm living off family money that is kind of dirty -- we wouldn't have it if we were Catholic all along.  If I can't get a job, will I have the strength to leave it all behind and be homeless?  Is that what God wants from me?  These are the questions that torment me.

I am not sure you should be especially concerned about living off family money when that money was originally gained through crime, etc.  You didn't do the crimes.  Wealthy American families who are rich through the slave trade of days gone by aren't culpable for what their ancestors did (I am, of course, talking about the immoral slave trade, and not those who were moral slave owners).  

I would think you would be more in danger of the loss of your soul on the streets than safely at home living on family money.  Now, that aside, you should certainly try to find a job if for no other reason that to give yourself routine in your day and to meet new people (whom you can then try to subtly convert!)