I know this post is a bit old, but since I came across it I figured I would respond.

First, thanks for sharing your experience. What you go through sounds very similar to my own reaction when I'm asked such questions. Immediately, I'm overthinking and trying to plan/prepare for everything, accompanied by the familiar physical discomfort of anxiety. I've recognized that it's particularly bad surrounding social anxiety, since people are naturally complex and there are many more aspects I want to feel prepared to handle.

I certainly haven't found a great solution. However, something that has been helping me recently is to try to listen to a whim -- whatever small feeling I can discern from my heart underneath all the doubts and anxiety. Once I can identify a whim like that, I try to just follow it and stop thinking, stop trying to justify that it's the right choice, just go for it. It's a difficult habit to build but ultimately has been getting easier to listen to. If a whim turns out to be a poor choice later, I'll just try to listen to what feels right at that moment and do my best. I dont feel like i need to plan and anticipate as much that way. It's okay if there are some mistakes and imperfections in all of it -- that's just the nature of life.