First, it sounds like you might be dealing with something clinical. Grief can often put you into depression, and if you were shy and found it hard to motivate yourself to start with, dealing with someone's death can make it just that much harder. Here are some non-medical things you can do to improve your mood chemistry:
1. Exercise, even if it's just a 10-minute walk every day. After 6 weeks of either exercise or Prozac, regular exercise has been shown to be as effective as antidepressants in relieving the symptoms of depression.
2. Find a grief support group
3. Eat a healthy diet and take a vitamin supplement
If you have the resources for it, you might find it helpful to go therapy, and/or go to a doctor and see if you are a candidate for short-term medication. You might also want to get your thyroid tested.
As for the immediate situation, it sounds like you have some pretty strong and deep-rooted stories about yourself, like "I'm shy and that's why I can't find a job and flunked out of college." Shyness is just irrational fear (fear of something that's not really fear-worthy, as in life-threatening) and you can choose to listen to it or not. Courage is not a lack of fear, it's being afraid of doing something and doing it anyhow. Your excuse is not that you're shy, your excuse is that you prefer being comfortable over going after the things you want. (Incidentally, this is one of the main symptoms of being a human being, so don't feel like I'm picking on you.)
The bottom line is that your feelings are not real. Your actions are. And you always have a choice.
Best of luck!
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"If ten million people believe a foolish thing, it is still a foolish thing."
- Anatole France
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