Right the moment you said "You've always winged it" I thought about age, my wife often tell me I sound old when I start telling her whats going to happen next on certain occasions, what is it about age that makes us think like that, is it because we fear? or because we are truly wize? I dont have adventures like yours but for sure sometimes I say F and go with it, after that I feel better, hope you the best ✌️
I don't know, I think we are told to be scared all the time. It's a full time job resisting that fear.
I don't think it's because we are wise. No amount of planning can avert disaster. You just need enough street smarts to get you through most situations and I've got that in spades.
I mean, it helped us out in India when the pandemic was announced. We knew that we'd be stuck and got out within three days. Younger people were so naive and just didn't think that would happen. We were telling them to go home but they were like 'oh, we might go to Nepal' but we're looking at it and the borders were shutting. WTF, we were thinking - are they not capable of reading?