I've always been goal driven — from annual goals, to quarterly goals, to weekly goals. But it was not until I talked to a successful founder that had two exits that he urged me to think about failure modes. Or, as he put it, "debugging."
So now I think proactively, in addition to goals, about points of failure.
It's not as a pleasant or exciting exercise, but it's extremely useful. Failure modes are very different from goals.
I find that, by knowing ahead of time what the failure modes are, I can better proactively protect against them.