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So here's my mindset I think will help you if you're like my friend.
EVERYTHING in life comes down to YES or NO. There is no grey area. MAYBE is NO because it's not YES.
Yes--and No.
Yes, it all comes down to yes or no.
No, you can't always see the end game from the first no, or first yes.
In principle your attitude is golden, but the "gray area" is in how much patience do you have for the number of yeses you have to get to get from point A to point Goal? It can look gray and murky if you lose focus.
Personally, it depends on my mood. If I am gaming and just enjoying the game, I might be willing to play for hours--not days, not weeks, but hours, sure--if I'm in a more direct mood, then point Goal has to be closer to point A, and I use a direct approach. Doesn't mean it will work, but as you say, the only question I have to ask myself is yes or no? But I still have to decide Yes, direct; or Yes, playful and indirect. Every Yes implies a plethora of negations, of adumbrated possibilities, of an edited reality.
As Zach Scott put it: "The only things you will later live to regret are the things you didn't do."
Yes.