The worst tax story that I ever had happened a few years back when I opened a company to publish greeting cards. After the fifth year of my accountant doing the taxes, she told me that I would no longer be able to write off my expenses because my business was a hobby. I did not understand at the time that there was an IRS rule regarding business vs hobbies and I thought that she was making fun of what I was doing. So after I told her off for several minutes, she explained to me that under the IRS code, if you open a business and after years of not making a profit, it is considered a hobby and you are not allowed to write off expenses like you would under a real business. I had to laugh at myself, but later cried because of the amount of taxes that I had to pay because I no longer had the write-offs.