I consider myself a businesswoman and I've got no problem packing whole purse and laptop into a backpack so that I can take it + rollaboard and avoid having to check a bag. OP it can be done, you just need a practical purse (not one that can hold a stadium chair) and don't try to take your entire wardrobe with you. If I'm nit planning to work during the flight, I'll occasionally tuck my laptop into my rollaboard, which makes the backpack lighter and easier to carry.

Kudos to the GA"s who actualy enforce rules--- I would just love more consistency here. Personally, I have had to overcome many obstacles in my career (female in a male-dominated industry). This ain't one of them.