Straight answers please. Estimated taxes: yes or no

Plus, how likely is the IRS to go digging to determine exactly when the income occurred? Unlikely unless there is something else on your return that will trigger an automatic red flag.
This isn't how the tax regulations are written. If you have non W-2 income it is automatically presumed by the estimated tax regulations to have been equally earned over the course of the year and hence you're required to pay equal withholding over the 4 quarters. That is the default requirement. You can specifically request a waiver from this if you have a demonstrable event that caused you to earn the money later in the year, and in this case the IRS will specifically look at the circumstance around your income and decide if they can allow you to go against the default and only pay estimated tax later in the year. But remember given the regulations presumption, it is you who must demonstrate when your income occurred and specifically ask the IRS to examine it, and if you can't demonstrate that it occurred later in the year, the default is that it occurred equally over the course of the year. So no digging is required by the IRS, it defaults to equal estimated tax payments and they only dig when you specifically ask them to in order to receive something other than the default. No value judgment on that, it's just the reality.
 
Short answer, YES, absolutely.

In general you have to pay estimated tax on ANY income and all income is assumed to have been received equally over the year. If you don't pay estimated tax you're hit for interest for the time it was unpaid, i.e. 9 months for Q1 estimated tax, 6 months for Q2....
There is an exception if you make all your money in Q4 as the result of a specific event, like you sell something big, for example, in which case you can request to consider it all Q4 income. The other loophole is if you have a business that is paying withholding tax for you. You could have the business withhold most of your withholding on Dec 31st and the IRS considers that to have been withheld evenly over the year for purposes of calculating estimated tax penalties, regardless of if this company has anything to do with trading.

You say pay estimated tax on ANY income? I have a full-time corporate job. And I'm trading on the side. And my trading has been doing really well. I'm being to think about taxes. But trading gains are considered CAPITAL GAINS and NOT income right? So I should NOT have to worry about estimated taxes? I don't have any entity formation. Just plain taxable account I'm trading.
 
You say pay estimated tax on ANY income? I have a full-time corporate job. And I'm trading on the side. And my trading has been doing really well. I'm being to think about taxes. But trading gains are considered CAPITAL GAINS and NOT income right? So I should NOT have to worry about estimated taxes? I don't have any entity formation. Just plain taxable account I'm trading.

You only should be worried if you don't want to pay any interest penalty on underpaying your taxes throughout the year. If you don't mind that, then there is nothing to worry about.

Any income applies to estimated taxes.
 
You say pay estimated tax on ANY income? I have a full-time corporate job. And I'm trading on the side. And my trading has been doing really well. I'm being to think about taxes. But trading gains are considered CAPITAL GAINS and NOT income right? So I should NOT have to worry about estimated taxes? I don't have any entity formation. Just plain taxable account I'm trading.
Any income, there is no differentiation between how you earned your money when it comes to estimated taxes. You have to pay 90% of your eventual tax bill or 100% of your last years tax bill under the safe harbor or you'll get hit with interest payments, full stop.
 
You only should be worried if you don't want to pay any interest penalty on underpaying your taxes throughout the year. If you don't mind that, then there is nothing to worry about.

Any income applies to estimated taxes.

Hmm... I hadn't realize that capital gains from trading falls under this. This year my trading so far on a monthly basis(ony 1 month so far) is exceeding my monthly salary! I know this is a good problem to have! haha. And February is shaping up to be a strong month too.

Maybe I should consult a tax accountant..
 
Any income, there is no differentiation between how you earned your money when it comes to estimated taxes. You have to pay 90% of your eventual tax bill or 100% of your last years tax bill under the safe harbor or you'll get hit with interest payments, full stop.

Hmm... I hadn't realize that capital gains from trading falls under this. This year my trading so far on a monthly basis(ony 1 month so far) is exceeding my monthly salary! I know this is a good problem to have! haha. And February is shaping up to be a strong month too.

Maybe I should consult a tax accountant..
 
Hmm... I hadn't realize that capital gains from trading falls under this. This year my trading so far on a monthly basis(ony 1 month so far) is exceeding my monthly salary! I know this is a good problem to have! haha. And February is shaping up to be a strong month too.

Maybe I should consult a tax accountant..
The easiest thing to do is just pay enough estimated so that your withholdings and your estimated payment exceed what you paid last year, then you're safe. You do probably want to calculate what your tax payment will be before you start trading in 2020 so you ensure you put enough aside to cover that since you wouldn't be able to claim those losses until 2021. But otherwise try to avoid paying estimated taxes especially this early because you might not end the year this far ahead and if so you just gave Uncle Sugar an interest free loan.
 
Only those are self employed are required to file quarterly estimates, but even if you don't it's no big deal - you simply would have to pay a fine which is interest based on the Fed fund rate.


From Turbo tax:

Anyone who is self-employed may be required to pay quarterly taxes. A self-employed person is someone who:
  • Is an independent contractor
  • Works in a trade or field as a sole proprietor
  • Is a member of a partnership that conducts business, such as an LLC
  • Runs a business on their own, including a part-time business

https://turbotax.intuit.com/tax-tip...s/a-guide-to-paying-quarterly-taxes/L6p8C53xQ

** I am not a tax expert - this is my opinion, you should verify this with the IRS or a qualified tax professional **
 
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