Over the past decade, I have done a ton of freelancing work on a lot of different projects, and that means taxes are sometimes incredibly difficult and confusing. This time of the year, I’m waiting for a variety of 1099s to arrive in my mailbox before I can even think about filing taxes and it will be a long process even when I have everything ready.

I’ve come to realize that the key to making this all work out without pulling your hair out and panicking a few times a year is to have a smart system in place at the start of each year. You have to be organized. You have to have a plan.

Here’s the truth: the system of personal income taxes in the United States is not friendly for freelance workers. There are many aspects of the whole tax system that put an unnecessary burden on people who aren’t hourly or salaried employees. There are rewards for freelance work, don’t…

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