One of my friends recently wrote on Facebook “how do you know what you want?” and I ended up writing a fairly long response. Posting it here, too.
You know, one of my friends just asked me this too, and I don’t know the answer for sure.
I think part of it was after a young lifetime of being a perfectionist and also a people-pleaser, I had to get good at satisficing or I was going to burn out. Going to progressively more difficult environments (high school to college to a job) meant that I was surrounded by an increasing concentration of people smarter than me, and that was something my ego had to adjust to. But learning that I actually *wasn’t* always the smartest person in the room also freed me from having to always Be The Very Best. I could just be Good Enough, and that was okay too.
So I was able to apply that to my own decisions as well. Is this thing the Absolute Best Option I Could Possibly Choose? Well, maybe, maybe not. But the marginal benefit of obsessing over Relentless Optimization is so stressful to me that I had to Just Pick Something.
And now that I think more about this: I think I cut my teeth on this skill with choosing restaurants with friends as a young adult. I get hangry when I don’t eat (it doesn’t seem to be a disorder, I just have/had a fast metabolism), so when people started dithering about where to go, it meant that I was risking a fainting+nausea spell. So I started doing Executive Decision Making for the whole group, and for the most part it turned out fine. Some people don’t like me telling them what to do, but Oh Well Their Loss.
Like a lot of skills, practicing in small ways helps build up the muscle (literal or metaphorical) for bigger tasks.
Anyway, IDK if this is what you were asking about, but I hope it helps! 
Emilybook 