This past week I started getting all of my tax forms. I got my W2 from the company I work for at my day job, 1099s from a variety of companies that I do freelance work for, some miscellaneous tax forms from investments that we have and reporting forms showing how much weve donated to our church and other charities.
Ive been using TurboTax for the past few years, and Ill be using it again this year so I started entering all of my information into their software a couple of nights ago (check out the tax software I recommend). Im still waiting on a few 1099 forms, but Ive almost received them all at this point.
After a couple of hours of entering data into the TurboTax interface I was shocked to realize that despite the fact that I had paid 100% of my tax liability from 2010 this past year, I was still going to end up owing quite a bit of money come tax time. In fact, it looks like Im going to owe about $5000 in combined federal and state taxes. Wow.

How did I end up in a situation where I owe that much money on my taxes? It happened for a variety of reasons.
First, when paying my taxes using TurboTax last year it automatically calculated what my estimated tax payments for the coming year should be. It printed out payment coupons for me for what I should be paying each quarter. The total of the payments it gave me was equal to 100% of 2010s tax liability. Knowing that I would be within the safe harbor requirements for 2011 taxes, I think that gave me a false sense of assurance that despite the fact that I was tracking blog income and expenses pretty closely, I wouldnt need to do any re-calculations if my income rose because I wouldnt be subject to any penalties. I could just pay any small overages when tax time came.
Another factor causing me to owe more than expected was the fact that my blog income rose more than I expected this year by between $15,000-20,000. Not only that but I had another one time increase in online income due to an online asset that I sold for around $8000. So the increase in blog income, along with a one time bump due to selling that property means I made around $25,000 more online this year than last year. I was expecting
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