In McRaven's book on Special Ops in the military he lays down the principles of successful operations:
Planning should lead to a Simple plan.
Preparation requires Repetition (role-playing on a rough set) of the proposed actions, and Security so that the enemy does not know of the plan and preparation.
Execution needs Surprise, Speed, and a focused Purpose. Surprise and Speed deal with the friction of war, Purpose is moral.
What you want is Relative Superiority. The probability of success goes up as you perform preliminary key events, but you then have to build relative superiority so that the probability will rise sufficiently so that you can complete the mission.
All of these categories should be thought of descriptive and analytic, to be observed as present or failing in an account of an operation.
I am not sure what to do with this in ordinary life. But I like the category system.