Dances with Gnolls
I totally get where @Jester David is coming from. It‘s a rare session that ends and I don’t feel like it could have gone better in certain places and a decent number where I end up kicking myself for a grand cockup (my melee on the run thread is just the most recent case) that upsets the flow of the game because of my incompetence.
I envy you DMs that have no trouble adjudicating actions and running the game, spending no time second guessing yourselves. Perhaps I’ll get there in another 10 years if I don’t give up due to my own sense of failure.
Yes it’s not ideal, but it really is quite common for those saying Jester needs to seek help. People try new things out all the time only to give up on it because it just didn’t work for them, a hardy few sticking with it until they achieve the skill they desire. I would guess it’s a small portion of the population that is happy having an entire evenings entertainment rest on their shoulders.
I second guess myself all the time. I just usually try to do that all after the session. In the shower or right before sleep, when I do my real thinking.
While I am running the encounters, I am usually too into it at the time, or just keep on going as if I didn't just make a mistake. Typically, my players don't notice, and it all works out into a fun evening.