You need to just get started. If you never get started, you'll never be successful.
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.
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.
I try to work the hardest I can without burning myself out.