And cold calling is the hardest part of sales. And yes, if you want to do work for hire, you have to be a salesman and not just a click click boy!. And confidence is a big part of it. Even if you have to fake it, show confidence in your work and convince them why they should let you shoot them. And DON'T be a "Bargain Basement Bob". Even if it is not true, people can be suspect of the bargain basement prices. Most know the phrase caveat emptor. If you don't know it yourself, commit it t memory!
The one tip I can give you is be assertive but not aggressive. What is the worst they can say, NO? It is not like than can take away your birthday and send you to the Middle East, right? Been there, done that s**t and got 3 Purple Hearts to show for it! Get used to a lot of no's before you get yes's. But remember, the portraiture business is very much a "word of mouth" biz. Don't be afraid to tell your initial customers to talk you up to their friends, and you will give them a break on their next gig with you if some new customers name drop them. Start up a customer email list and keep in touch. Let them know when you are having holiday specials.