It's very important that you stay comfortable while shooting Headshots outdoors in NYC. Remember that no one in New York cares, but even so, people still feel uncomfortable!
I can't stress enough that New Yorkers don't care if you are getting a headshot session taken. Just think about it, they walk by you, look for a minute, and then walk away. Then they forget.
If you aren't famous and the photographer isn't famous either, no one will care. And if you are famous, then you should enjoy the fame. Remember anyway, if you are an actor and you feel awkward getting your headshots taken, then you should find another career.
You have to love the camera! Your whole career is based on your looks and your acting skills, so being camera shy is not going to help.
If you're not an actor and you're getting corporate headshots taken, try not to think about it. Enjoy the publicity while it lasts. Remember that outdoor headshots usually come out much better than indoor headshots, especially in New York where you can get beautiful reflected light from building sides. So go out there and just do it!
Get your headshots and enjoy the publicity in New York, and get what you paid for. If you are worried the whole time, your images will look bad.
But remember, if you really are worried about shooting outdoors and you are thinking of hiring me, just let me know and we can shoot indoors in my studio.
Good luck and ask if you have any other questions about New York Headshots!