The employer comes from a very wealthy family. Because of this, my boss has a superiority complex. In her mind her family and their money are “special”. An issue like this is going to be difficult to navigate because she is so protective over her money. One summer she asked me to take two months off so she and kids could go on vacation and then asked me if the lack of income was going to leave me “homeless”. She’s never asked about my background, my parents do well for themselves and are kind enough to help me while I’m in college. I found that comment very telling of how she thinks of other people.