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posted Sep 30, 2021 9:42:41 AM

Taxes for Stock Market

My husband made a good amount this year day trading in the stock market. We are trying to come up with better ways to lessen the amount we will pay on taxes. Would donating a large sum to charity help if it gets us to itemized deductions or will it not make that much of a difference? Any other tips?

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3 Replies
Employee Tax Expert
Sep 30, 2021 9:58:41 AM

Hi Reedalotofbooks50,

 

Yes, making large charitable contributions could potentially increase your itemized deductions.

 

You should also fully fund any retirement accounts to which you are eligible to contribute (I don't know your ages or work situation so I can't be any more specific than that). 

 

If you or your husband hold any investments that have unrecognized losses, you could sell them before the end of the year to capture the losses. Just be sure not to repurchase the investment within 30 days or it would be considered a wash sale and you wouldn't get to claim the loss. 

 

You could also look at purchasing investment property, which might result in a tax loss. 

 

Also, remember that the only reason you're thinking about this is due to a large unexpected increase in income. There's nothing that says you can't simply pay the taxes on this and enjoy the remaining part of your windfall. If you wanted to do these things anyway, and having this extra income makes it financially feasible, that's wonderful! Definitely take advantage of it! And smart tax planning is always a good idea. But don't let the tail wag the dog. There's nothing wrong with paying more taxes when you have more income - that's how our tax system works. So, I wouldn't recommend doing things you otherwise wouldn't consider *just* because they reduce your tax bill.

 

Hope this helps your thought process!

Level 15
Oct 26, 2021 5:22:36 PM

at best a charitable contribution saves you only about 40% of the amount contributed so it costs you out of pocket $ .60 or more to make a $1.00 contribution.  before year-end, if it's sensible from an investment standpoint, he could close out loss positions.  we know nothing else about your taxes so maybe it would be advisable to sit down with a tax pro to do year-end tax planning. 

 

further, maybe if he does enough trading he can elect to be taxed as a trader using the 475(f) election - (first year available would be 2023 because the election to use it must be filed by 4/15/2022 (for 2021 had to be by 4/15/2020 and for 2022 had to be by 5/17/2021 so it's too late for those years)  this would allow setting up retirement plans, being able to deduct health insurance.

 

trader per IRS eligible to make 475(f) election

Traders

Special rules apply if you're a trader in securities, in the business of buying and selling securities for your own account. The law considers this to be a business, even though a trader doesn't maintain an inventory and doesn't have customers. To be engaged in business as a trader in securities, you must meet all of the following conditions:

  • You must seek to profit from daily market movements in the prices of securities and not from dividends, interest, or capital appreciation;
  • Your activity must be substantial; and
  • You must carry on the activity with continuity and regularity.

The following facts and circumstances should be considered in determining if your activity is a securities trading business:

  • Typical holding periods for securities bought and sold;
  • The frequency and dollar amount of your trades during the year;
  • The extent to which you pursue the activity to produce income for a livelihood; and
  • The amount of time you devote to the activity.

If the nature of your trading activities doesn't qualify as a business, you're considered an investor and not a trader. It doesn't matter whether you call yourself a trader or a day trader, you're an investor. A taxpayer may be a trader in some securities and may hold other securities for investment. The special rules for traders don't apply to those securities held for investment. A trader must keep detailed records to distinguish the securities held for investment from the securities in the trading business. The securities held for investment must be identified as such in the trader's records on the day he or she acquires them (for example, by holding them in a separate brokerage account).

Traders report their business expenses on Schedule C (Form 1040), Profit or Loss From Business (Sole Proprietorship). Commissions and other costs of acquiring or disposing of securities aren't deductible but must be used to figure gain or loss upon disposition of the securities. See Topic No. 703, Basis of Assets. Gains and losses from selling securities from being a trader aren't subject to self-employment tax.

Level 15
Oct 26, 2021 10:06:17 PM

If capital gains tax bothers you, the only way to lessen that is to wait at least one year and a day before you sell for a profit.

After a decade or two if your stock goes up, you reach a point where you can never sell.

(Note to Elizabeth Warren: That's why billionaires never sell.)

OR

Some investors will sell losers also to offset gains.

There's no tax, but there's no profit either.