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5 Year-End Tips to Minimize Your Investment Taxes

There are ways to reduce your investment taxes, especially after a year in which you probably sold some losing stocks. Here are 5 tips to limit the damage.

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There are ways to reduce your investment taxes in a strong year that may have seen you sell some winners. Here are 5 tips to limit the damage.

The combination of a strong year in the equity markets (Dow and Nasdaq up about 20% and S&P up 26% YTD) and some challenging and choppy action of late has likely led a lot of investors to book some profits at the end of the year. Unfortunately, booking profits means you’ll be dealing with short- or long-term capital gains depending on your holding period.

The end of the year is our last chance to potentially offset those gains and is always a good time for us to take stock of our finances, assessing how well we did during the year managing our income and expenses—and most importantly—how we can keep more of our money and give less to Uncle Sam. Consequently, these five tips for reducing your investment taxes are designed to help you do just that.

Five Tricks to Reduce Your Investment Taxes

Tax Harvesting. This strategy helps to offset your capital gains with capital losses when you do your investment taxes, a method to sell your losers to reduce the tax hit that is incurred when you sell your winners. If you have held on to a stock that just hasn’t performed as you anticipated, or you want to rebalance your portfolio, now is the time to cut your losses and sell the losers, for a possible tax advantage.

Loss Carry-Forwards to Offset Ordinary Income. In the same vein, if you are holding a portfolio with several losing stocks, and the rest of your portfolio has given you some very nice gains, you may decide to “bite the bullet” and unload all the nonperformers. The IRS allows you to offset ordinary income by using up to $3,000 of your excess loss. And if you have more losses than $3,000, you may carry them forward in future years. But please remember the IRS wash sale rule, which requires that you wait 30 days after selling a losing stock before you can buy it back at the discounted price.

Don’t Trade as Much. Every time you cash in a stock for a profit, you generate a capital gain. If you hold a stock for less than a year, you will be socked with a short-term gain, taxed as ordinary income. But if you keep it for longer than a year, your gain will be taxed at the lesser capital gains rate. With the recent changes to tax laws, the capital gains tax remains the same, 0%, 15% or 20%. But the rates no longer depend on your tax bracket; the new law requires they be applied to different income thresholds.

Take Advantage of Tax-Deferred Accounts. As you are well aware, investing in tax-deferred accounts, such as a 401(k), 403(b), a SEP plan (for business owners) or an IRA allows you to stockpile your savings and defer payment of taxes on your dividends, interest or capital gains until you withdraw money from the account.

The following graph from compares the tax savings of placing a $250,000 bond in a taxable account vs. a tax-deferred annuity and a tax-deferred IRA. It’s a pretty significant difference!


Make Sure Your Assets are Allocated to the Right Accounts for Tax Efficiency. Your investments that generate the highest taxable income—assets such as high-turnover mutual funds or Real Estate Investment Trusts, and taxable bonds—may be best-suited for accounts that provide tax advantages, such as 401(k)s and IRAs. Alternatively, assets like munis, stock index ETFs, and long-term equity holdings—where taxes are minimized—would be better served in a taxable account.

The following chart, also from Fidelity, explains the tax treatment of various investment vehicles, and how they may be treated if held in taxable, tax-deferred, or tax-exempt plans.

This chart should help you plan your investment taxes this year.

I hope these ideas for how to do your investment taxes help you hold on to more of your hard-earned money. As you can see, it pays to plan—not just your investing strategy, but also how to maximize the tax savings on that strategy.

Does tax loss harvesting play a role when you’re considering selling underperforming stocks?


*This post has been updated from a version published in 2018 and is periodically updated.

Nancy Zambell has spent 30 years educating and helping individual investors navigate the minefields of the financial industry. She has created and/or written numerous investment publications, including UnDiscovered Stocks, UnTapped Opportunities, and Nancy Zambell’s Buried Treasures under $10. Nancy has worked with for many years as an editor and interviewer for their on-site video studios.