Many many external circumstances are outside of your control, but will affect the outcome, and you have to be OK with that.
My advice is flip a coin. If you regret the way it landed, then go with your gut.
You need to just get started. If you never get started, you'll never be successful.
I try to work the hardest I can without burning myself out.
I try to keep the meetings small, especially when we're doing product design.
I find it hard to manage somebody's work unless I have an intimate knowledge of how to do it myself.