My main paying side job right now is going well. So far the client hasn't gotten spooked at any of the "here's stuff I don't know", "here are areas where you probably want to bring in someone else to work with me because I lack these skills", or "here's how much money I want". They're providing useful feedback but not micromanaging and we seem to be on the same page regarding what the deliverables should be for something that's interesting for me to work on.