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My name is Jacob, a husband to a wine-blogger wife, father to two bouncy-boy toddlers, and I'm the owner/author of My Personal Finance Journey. By day, I am a scientist working in bio-pharmaceutical development. Personal finance has been my hobby since 2007 when I started teaching myself through books (that finance B.S. degree didn't teach me much!). Learning how to save, adopt a frugal mindset, and invest my own money soundly has allowed me to have a savings rate > 50%, increase my net worth by > 20 times, grow my career, and always do what I love. Check out the About Me page to learn more!

This year I got a surprise when I finished up my taxes.
I owe quite a bit to the federal government. Why do I owe money? The answer for my situation is simple. I earned income on the side.
Anytime you earn income on the side of your regular job, you are required to pay taxes on it. The government wants their cut of everything that you make, so even if you get paid in cash, you are still supposed to report it. While I knew that I was going to make extra money last year, I didn’t realize how much. I could have avoided having to pay this year (plus any potential penalties) if I would have just properly estimated my taxes.
Estimated taxes are payments that you make to the government to cover your tax liability on income not subject to withholding. A common form of this income would be earned through self-employment. Even though I am employed full-time, any extra income that I make on the side from freelancing and running a small business is considered self-employment income. Other applicable income includes interest, dividends, alimony, proceeds for the sale of assets, rent, and prizes/awards.
Anyone who believes they will owe more than $1,000 when taxes are due should be prepared to pay estimated taxes. If you had a tax liability for the previous year, then you might have to pay estimated taxes.
It can be difficult to calculate how much you will need to pay for estimated taxes, but the IRS does have a calculation worksheet. They include it on their 1040-ES form. This form provides great detail into when you will have to pay and also helps you calculate how much you will owe. There are a few ways to calculate your estimated tax liability.
100% of previous year – If you owed more than $1,000 when you filed your return, then the safest way to deal with estimated taxes is to go with 100% of your previous years taxes. This would be to simply take what you owe to the federal government on your previous return and that would be what you need to pay. If your previous year’s adjusted gross income was more than $150,000, then you will need to go with 110%.
100% of current year – This number can be hard to know. You can use the IRS worksheet or software like TurboTax to help you calculate this number. If you are going to make the same salary, but can estimate how much you will make on the side this year, then this method can work. You use this calculation to ensure you don’t owe again on the next return. You do have the ability to change your calculation during the year, especially if your income fluctuates.
If you don’t estimate your taxes properly, then you could owe a penalty. I had to pay one this year because I didn’t meet the criteria to have the penalty waived. This is an underpayment penalty. The penalty is currently an annual 4% of the amount you underpaid each period. This penalty can be avoided if your tax payments for the year exceed the lower of these two withholding scenarios:
You could also owe a penalty if you don’t pay your estimated taxes on time. If you are past their specified due dates, then you could be eligible for a penalty.
If you have your estimated taxes calculated, then it is important to understand how to pay them. The 1040-ES form comes with four payment vouchers. This allows you to split up your estimated tax liability into four payments. These can be equal or you can change the amounts depending on your calculated income. The IRS has strict payment deadlines. Here are the due dates for this current year.
1st Payment – Due on April 15th
2nd Payment – Due on June 16th
3rd Payment – Due on September 15th
4th Payment – Due on January 15th of the next year
If you want more in depth information about due dates and how you deal with them, then read more from the IRS estimated taxes section.
The IRS provides you with three ways to pay your estimated taxes. They are:
If you don’t want to deal with paying the tax on your own, then you can have your employer withhold more on your regular paychecks. This only works if you are receiving paychecks. You would need to resubmit an adjusted W-4 to your employer requesting that they withhold more than they normally do. You will still need to make sure they are withholding enough so you don’t owe when you complete your return.
The debate continues on whether you should deal with taxes yourself or hire an accountant.
I have used TurboTax for years and it makes my taxes easy. It even helped me calculate the estimated tax payments for this year. That being said, I believe next year will be time to hire an accountant. We are selling our home and buying another, along with me cashing in some stock options, and making more side income. This year’s taxes are going to be complicated and I want to make sure it is done right.
(A side note from Jacob: I was quite surprised how affordable an accountant can be. Some of the premium plans for online tax prep platforms can charge you around $90, whereas, some accountants cost less than $300 to prepare your taxes.)
If you don’t feel comfortable calculating your estimated taxes, then seek professional help. There is no need to get it wrong and have to pay a penalty just because you didn’t understand the calculations. If you are tax savvy and you can use the TurboTax or H&R Block software, then feel free. It will cost less than a tax accountant and give you a little more insight into how estimated taxes are done. Either way, feel comfortable with the option you choose and make sure you properly calculate and pay your estimated taxes.
How about you all? Do you have to pay estimated taxes for your income that is not taxed when it is paid? How do you pay your estimated taxes – online, via check, or on the phone?
Do you use an accountant to file your taxes?
Share your experiences by commenting below!Â
***Photo courtesy of http://www.flickr.com/photos/moneyblognewz/5610981299/sizes/l
Hi folks! My name is Jacob. I am the owner and operator of My Personal Finance Journey. I started this blog in January of 2010 and have enjoyed the journey ever since. Since finishing up graduate school in Virginia in 2014, I have been working in biopharmaceutical development in Colorado. You can read more about me and this site here​. Please contact me if you have any questions!
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I’m working full-time now without side income so I don’t need to do estimated taxes anymore. I did when I was self-employed though and it was no fun! I did the worksheet from the IRS and I paid online but I still ended up owing quite a bit on taxes! I used an accountant this year and had an okay experience. Next year will probably do it on my own as taxes are simpler with just a steady W2.