Basically, if I can handle the situation off "intuition", then I'm fine. If intuition fails, then I need to sit down, do some reasoning, and build a better intuition.

Or, in other words, if you KNOW you have a problem, then sit down and solve the problem. AVOID going off and looking just to see if you MIGHT have a problem.

The key here is that you should never reason about the immediate challenge. Don't ask "what should I order today?", instead ask "How should I determine my order in the future?" (I'm very fond of the "first item that looks appealing, and then immediately put away menu so I don't see any conflicting options" - the lost utility from a "sub par" decision is far outweighed by the utility I would have lost agonizing over the choice, and there's a fair amount of research to back this up)

As an example: I rarely have any trouble deciding what to wear in the morning. Since I don't have a problem, I don't think about it at all. A few months ago, however, I decided I wanted to wear skirts more, so I reasoned out that I should (a) buy more skirts and (b) rearrange my closet so that skirts are very accessible while my slacks are off to the side.

P.S. Not sure if it's a useful pointer, but this idea came to me after a recent re-read of "The lens that sees its flaws" - the goal is not to spend time hunting down possible flaws, it's to fix the flaws we are already aware of. It's definitely an area I'm still just beginning to explore, though.