When I was growing up I played all kinds of board games... Life, Clue, King Oil, Chess, Checkers, Candyland, Risk, Chutes and Ladders, Spades, Hearts, Poker, Backgammon, and several, others. I won more than I lost, but many times I won with just good guesswork.
Skills from game playing carried over to education and life skills like judging character. I won most of the time there too, but it still included some guesswork.
Over time, life skills improve so that guesswork is at an absolute minimum. I am more and more certain of what makes me happy, for example. And I know, without guessing, who I can trust and who I want to surround me. And it is certainly not a guess who brings a smile to my lips and contentment to my heart.