Are God's chosen usually predestined to be successful in life?

By successful, I guess you mean rich. Or do you mean happy and healthy? In any case, I am one of God's chosen (Jewish) but not in any way rich. I am happy and healthy though. A friend of mine once explained the problem of people with a bad attitude - a dark cloud. He said that they needed an operation called an "operectomy". This operation severs the connection between the eyeball and the butthole so they stop having a shi**y outlook on life.