For me, the thing that helped me relax and stop counting everything was getting into a routine. I eat lunch out a lot, so I found 3 places that had good items that I could eat freely, and I ate at those places a LOT. I also have the luxury of living with only 1 other person, who's also mostly primal, so there isn't much of anything in the house that's so "bad" I need to count to see if I can have it.
The other thing is that sometimes it just takes time. Once you get to a good size & shape (screw the scale, listen to your pants!) and stabilize there for about a year or two, you'll be fine. At some point you will be able to let go of that nagging voice that says "What if..." because you can answer "Hasn't happened yet, I think we're good."
Good luck! Let us know how you do.