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There was a time, not long ago, when I feared April 15. I had always managed not to pay enough throughout the year, that I had a fairly big payment due. (I have a lot of kids, and hence a lot of deductions, but self-employed people must pay the dreaded "Self-Employment Tax," which is a full 15% off the top. There is no getting around it other than paying small chunks on a regular basis. I have found that monthly is best.