How many vacations can I get away with taking in one year? I work for myself so I don't have to clear it with a boss and my assistant is more than capable of handling the phones and keeping things on track once the contract is signed and all the vendors have been hired. Doomsayers, dragons, all of that I can handle. An earthquake damaging the buildings around my office before we get to move in and my best friend's boyfriend almost dying ending up in the hospital in the same week is pushing my limits.