If you ever want to face your insecurities head on, pick up a phone and ask someone for money! This has proven to be a test of my character. Dialing for Dollars, as it's called, will be a constant activity in a campaign.
When I first started calling people to ask them for money, my conversations went something like this. "Hi! How have you been? Oh, that's good. Well, uh... I'm running for City Council and well, I really hate to ask for money but I was wondering if maybe you had something you could donate to help me?"
There is lots of research on psychology of asking for money and the way I started out didn't instill confidence in people and it was framed in a way of them doing something to help me.
I've learned a lot since then. I'm still not a master but the conversation is supposed to go more like:
"Hi! How have you been? Oh, that's great! Listen, I'm calling my good friends because I wanted to let you know that I'm running for City Council here in Rochester and I know how much you care about childhood poverty and my campaign will be working to advocate for mental health programs embedded in the community to help kids and parents overcome poverty induced trauma which is a major barrier to success. But to run a successful campaign, we need money. We need about $400 to send out campaign flyers. Would you be able to help by making a donation tonight?"
This last conversation ties their interests to the campaign and how your campaign will help them achieve one of their goals. It also let's them know how their money will be used and creates a sense of urgency.
This is easier said than done because it can take some time to make those correlations and over the course of a phone call it can be hard to hit all the key points. BUT this is something you will have to do a LOT and practice makes perfect!