One thing that I did not anticipate when I decided to become a bookkeeper was the the way shame or embarrassment would be a regular point of conversation with potential (and sometimes even current) clients. I definitely find myself slipping into the role of counselor and advisor in a real and intimate way for clients and "might become" clients. This was surprising at first. But it makes sense because we all hold a lot of weird feelings around money and success and having our shit together.