Sometimes you need to stop the game of tug of war before you can proceed with a successful Whole30. Take some time to "drop the rope" and walk away from this constant back and forth you are experiencing. Perhaps experiment over the next 2 or so weeks with some paleo recipes (get Well Fed!). Have your dessert, have your wine or whatnot - and give yourself some time to really prepare mentally. Write down all the reasons you want to do a Whole30. Write down your goals. Write down all the things that came up when you've tried in the past that made you get off track. Prepare your mind. Set a date for a few weeks from today. Read the books. Read the success stories. And then commit.