Joshua_Blaine comments on May Monthly Bragging Thread - Less Wrong Discussion
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I have reduced my discomfort with talking to anyone about anything, especially requests for help/information. Instead of avoiding talking to people like my parents, teachers, or businesses due to some odd, misplaced anxiety I've successfully started noticing this pattern and purposefully overcoming it.
Examples include:
Talking to my family about wanting to move to Australia, instead of putting it off until the last minute.
Calling several local banks and asking about shadowing opportunities, something unfamiliar to both me and the banks.
It's not incredible, but it feels nice to be making progress in the right direction.