How to choose what to do?
A simple rule
If after a long time you still don’t know what path to take, choose the hardest one. Always. No matter what happens, you’ll have the peace of mind of having tried. The resentment of the easy way out will haunt you forever.
There are more possible chess matches than particles in the universe. Do you think you can compute all possible outcomes and dangers ahead of you? No matter what decision-making framework you use, you’ll always need some type of faith.
Go in there and loose. Win. Loose again. Repeat.