"Be bolder" is different than "what do you think a bold person would do?"
I have had many conversations with people going through a tough time and unsure of what to do or how to feel in a situation and there is this trick to getting people to think differently that almost always works... ask the question
"What would a reasonable person do in your situation?"
Suddenly the person having trouble coming up with the answer "What should I do?" has a perfect answer to "What would a reasonable person do?"
It's a psychological trick that goes after how one thinks about one's self and how one thinks about someone else being quite different. If you refocus your attention to view yourself from an external objective, you often end up with much better judgement.