Earlier quoted context omitted.
For many situations, having really good radar so you know how to avoid stepping in it before it puts you on a slippery slope is the only hope of avoiding the necessity to take a stand. I'm fortunate in that I seem to have a natural knack for such things (and have intentionally honed it with both formal and informal study). Of course, one problem with being good at something like that is that it essentially cannot be…
Good radar or no, you still have to keep an eye out for the unknowable "black swans". In any case, good radar for trouble just means you've traded away most of the peace of mind that comes with obliviousness in exchange for an unquantifiable reduction in hassles.
There is some truth to that. I do, at times, fret too much. So there is some cost in terms of peace of mind. However, even though I cannot prove to other people that there is a cause and effect relationship (between my actions and specific outcomes) and even though the reduction in hassles cannot be quantified with exactitude, that doesn't mean I cannot quantify it sufficiently to conclude that the benefit is well worth the cost.
For example: My divorce was amicable and there were no lawyers. IIRC, the average cost of a divorce lawyer when and where I got divorced was $18,000. No, I can't know if I "would" have spent $5000 or $18,000 or $40,000. I can know that I saved thousands of dollars on lawyers fees by having an amicable divorce. I am also very certain that it benefited me by more than that: I got thousands more from my husband than I was legally entitled to. My husband was not a wealthy man. After paying lawyers, there wouldn't have been that much to fight over. (He had a job, we had a bunch of debts and some household possessions.) I have every reason to believe that the approach I took was all to the good. Can I prove that to skeptics beyond a shadow of a doubt? No. Can I measure it with a high degree of confidence for my own peace of mind? Yes.