Can you follow the Paleo Diet as a working professional?

So I have recently had some health issues and my doctor has recommended i check out the paleo diet/lifestyle. It seems really awesome in theory but i want to know how do you guys figure out if something is paleo if your at a restaurant with friends or coworkers and when your shopping at the grocery store and does it require a lot of ahead of time planning because Im not sure if I can follow something super strict but Id like to know how you guys deal with that. Thanks guys