I started to read your post and then I got a little lost but I can tell you a few things.
Certainly leadership is not easy because of the responsibility it entails but I think that many people in the world prefer that someone else makes the decision for them and simply follow them, it is a very comfortable attitude but also risky. 
Between dipping my toes in little by little or jumping in all at once I usually do the latter, sometimes it works out well and sometimes it doesn't, life is like that.
I'm also addicted to coffee and here while I'm writing I've had two cups of black coffee and one with milk.
Greetings, I enjoyed reading you.