I hear frequently that fundraising is scary, or that asking people for money must be a horrible job. I have some advice for losing the fear factor and being at peace with your job as a fundraiser.
I don't approach fundraising thinking about "the ask." Instead, I simply try to make friends. If I encounter people who are passionate about the same things I am, I will likely want to be their friend anyway. I will want to share musical and arts experiences with them, argue over who writes the best sonatas and learn about other mediums that I don't get exposed to as much.
We all know that to enjoy the arts we have to pay. Some of us can only afford discounted tickets and others can afford to underwrite. Each person on the financial spectrum should become a friend. Through the course of the friendship, opportunities will arise for people to spend money, and they will gravitate to the level appropriate for their means. There could very well be outside factors that move the conversation along, like the end of the fiscal year or a looming membership deadline. The key is to not let those factors pull focus away from the friendship you have developed with this person surrounding your shared interests (presumably it is a shared interest for which you are fundraising).
This friendship philosophy creates a new kind of "ask." You are no longer asking a wealthy person to give you money; you are now asking a friend to help make your shared passions/interests available to more people.