Another tip I just started trying to work with - if you're feeling to shy or scared to ask for something, whether it's a raise, an informational interview, whatever, ask a friend to write it for you. They're more likely to hype you up and feel unashamed to help you get what you deserve.
If you don't trust them to write it for you, ask them to at least hit send! Even that small action can help you feel removed from the ask.
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