Like most very small businesses, I have had to pay Estimated Quarterly Taxes for about twenty years now. I was first introduced to this ritual by tax preparers. After we finished filing my taxes for the previous year, they gave me four little slips of paper, one for each quarter. Each slip of paper had a dollar amount written on it, the amount I was supposed to pay in estimated taxes for that quarter, based on my income and tax rate from last year.

But in the wild world of self-employment, last year’s income doesn’t necessarily have much similarity to this year’s income. Plus, the “quarters” vary greatly a lot in actual length, from two to four months. I wanted to pay amounts which were more based on my real taxable income for that quarter. For example, between April 15 and June 15 is a two-month “quarter”; I wanted to pay estimated tax on my actual income for those two months, instead of an amount based on three months of my last year’s income.

So I developed my own system which I’ve been using for about twenty years. Just before each government quarter deadline — January 15, April 15, June 15, and September 15 — I figure out my actual income for that quarter. I multiply that by my tax rate, to the best of my knowledge, and send the estimated payments to the U.S. Treasury and my state. This system hasn’t failed me yet, by my standard, which is that I’ve never owed anything in April.

I also learned to pay estimated taxes via the internet and have been doing that for about ten years now. I was able to pay quarterly estimated taxes right from my laptop in Mexico. It took a little effort to get set up to do this, but it’s well worth it to save all that time year after year. Writing out checks and addressing envelopes might not seem like such a big deal, but considering how arduous and frequent this process is, I’m happy to just click a few times and send my hard-earned money flying off to Uncle Sam.