People in my life routinely talk about how lucky I am. Its a big enough thing that it's kind of a meme. I think a big part of it is strategic disassociation. You can't do it with every decision in your life but if you pick and choose some focal points where you just pick the choice with the unknown but possibly positive outcome, commit to it fully, and internalize the value of the joy of discovery without worrying about it too hard you often come out ahead.