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What Is Tax Selling?


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    Highlights

  • Tax selling allows investors to sell assets at a loss to offset capital gains and lower tax bills
  • Wash sales, which involve repurchasing the same asset within 30 days, are prohibited by the IRS and disallow tax benefits
  • This strategy often occurs in November and December, potentially creating buying opportunities for oversold stocks
  • Investors can maintain their positions by waiting 30 days before repurchasing sold assets
Table of Contents

What Is Tax Selling?

Let me explain tax selling directly to you: it's a strategy where you, as an investor, sell an asset that's showing a capital loss specifically to reduce or wipe out the capital gains from your other investments, all for income tax purposes. This approach lets you dodge paying capital gains tax on assets you've recently sold or that have appreciated in value.

Key Takeaways

Here's what you need to grasp: tax selling means selling an asset at a capital loss to cut down or eliminate capital gains from other investments for tax reasons. A wash sale happens when you sell an asset via one broker to claim a loss but buy it back through another within 30 days. Remember, the IRS strictly prohibits wash sales.

Understanding Tax Selling

When you engage in tax selling, you're selling stocks at a loss to shrink the capital gain from another investment. Since capital losses are tax-deductible, you can use that loss to offset gains and lower your overall tax liability.

Take this example: suppose you have a $15,000 capital gain from selling ABC stock. If you're in the top tax bracket, you'd owe 20% on that, which is $3,000. But if you sell XYZ stock at a $7,000 loss, your net gain drops to $8,000, and you only pay $1,600 in taxes. See how the loss on XYZ directly cuts your tax on ABC?

You might be tempted to sell at a loss, claim the deduction, and buy back immediately to game the system—that's a wash sale, and the IRS won't allow it. Specifically, if you sell through one broker and repurchase the same or similar asset via another within 30 days, it's a wash, and you lose the tax benefits.

Tax Selling vs. Wash Sale

Tax selling lets you keep your overall position while booking a capital loss, and it's perfectly legal. Wash sales, on the other hand, are illegal. This practice usually targets investments with big losses, so it often hits a few specific securities in the market. When many sellers dump shares at once, prices can drop sharply.

Once the selling frenzy ends, those oversold shares might rebound. Tax selling peaks in November and December as investors lock in losses for tax season, which could mean the best tax-selling targets are poised for gains early next year.

A smart move for you as an investor is to buy during this tax-selling period and sell once the loss is realized. If you want to repurchase what you sold, wait until after the 30-day wash sale window. Also, ensure the shares were held for over 30 days before selling for the loss.

How Does Tax Selling Benefit an Investor?

Simply put, tax selling helps you avoid capital gains tax on assets you've sold or that have gone up in value.

What Does Tax Selling Involve?

It involves selling stocks at a loss to cut the capital gain from another investment, using the deductible loss to offset gains and reduce your tax bill.

Can an Investor Maintain Their Position Through Tax Selling?

Yes, you can maintain your position while taking the capital loss. It typically focuses on investments with significant losses, concentrating on a small number of public market securities.

The Bottom Line

To wrap this up, tax selling is your way to sell an asset at a capital loss to reduce or eliminate gains from other investments for tax purposes. It directly helps you skip paying capital gains tax on recent sales or appreciated assets.

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