I only have Jack Black Lip Balm in my purse. If it’s a special occasion, I usually bring along whatever lip products I wore!
The biggest thing is practicing — the more you do it, the more comfortable you get with it. One thing you can do is to apply it before you do your eye makeup, because if you make any mistakes, you can easily remove it entirely without ruining your pretty eye makeup. You can either try to apply your actual eyeshadows and the like around it, or not worry too much about it and then carefully go over the line again at the end.
A space themed collection, maybe! How about a Mellan collection? Eh?