One of the things about being a freelance writer, well, one of the many things, is that you end up writing for so many different people that tax time can get pretty crazy. If you haven't saved money throughout the year for the year-end money grab, there are a lot of ways to maximize deductions, so that usually isn't a problem for me. But, the volume of 1099s can get a little overwhelming.
The first issue is just keeping track of how many you have coming to you and waiting for them all to come in. If one doesn't show up, you then have to remember who it was coming from and contact them about it. If they all show up in time, you then have to keep track of all of the little people who aren't required to send one but that you nevertheless owe taxes for. The combination of the 1099 avalanche and the small project record-keeping is enough to make you want to move to the woods and live on dandelions and wild hamsters.
So, how to make sense of the mess? Well, I use a complex system of proprietary software that allows me to fill out up to 75 pages of income lists and attach pictures of all my clients. I then pay thousands to an accountant that specializes in freelance writers. Just kidding, I just print out everything I need to remember and put it in a big pile. The pile may be large, but my courage in the face of taxes is larger.
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