Forget about overthinking a situation so that you do the most good in it. Indefinite good judgement at first attempt is a myth.
Good judgement comes from experience.
Experience comes from bad judgement.
Think of it as if you’re walking on a winding tightrope of a path blindfolded the entire way with your arms held far out. You could accidentally walk the tightrope perfectly the entire way turn by turn (and one of a billion monkeys with a billion typewriters could write a masterpiece), but most likely you won’t. You’ll fall, and have to pick yourself back up again; over and over and over again.
Just because there’s a right path does not mean that you’ll walk it all the time. You are blindfolded afterall.
James J. “Jim” Horning