Work issues

So I recently started a new job the first week of January. I am a dispatcher for a local towing / recovery business. And I honestly don’t think it’s going to be a “career”. I mean I like my boss and everything but he always kind of contradicts himself. Like he will tell me to ask any questions I have and to not be afraid to. But when I do ask questions he sounds annoyed that I’m asking them, and like I should automatically know even if I was never told. Idk I just feel like I can’t win either way. Idk , I just feel so overwhelmed like I can’t do it. Anyone have any advice?