I am hung up on the process of designing a logo for my friends side project. It's a new and small side business and they haven't put a lot of thought into branding, design etc. I know most of the major elements that need to go into the logo, but the lack of overall clarity from my friend has me spinning my wheels x10 than normal. I am still a fairly new designer, and I still don't consider logos my strength, but I want to. I am also a chronic over-thinker! I have made and tossed 100 drafts and feel like I'm still back at square 1.

What is the best step to take here? I have taken time away from the project, but there is a deadline. Should I ask my friend some questions to help define their brand & direction a little more? Or is this just more overthinking on my behalf? As a designer, what would you do in this situation? Does anyone have suggestions for the best questions to ask?

I feel like my friend will be very happy with whatever I come up with. I just need something simple but I am banging my head into the wall and nothing I come up with feels like it "fits." I feel like I struggle to find good sources of inspiration for logos sometimes as well. I feel like I can use any help I can get right now!