Using Tax-Loss Harvesting to Minimize Capital Gains Taxes

Using Tax-Loss Harvesting to Minimize Capital Gains Taxes

So far, in 2023, investors are enduring a bit of a roller coaster ride, with stocks producing gains through mid-year and sliding into losses toward yearend. While stock market downturns are inevitable, there’s no way to predict when they will occur or how long they will last. If investors are seeking a silver lining while anxiously watching their portfolio values decline, it’s this: you haven’t realized a loss until you sell your stocks.

Investors with a historical market perspective know that every downturn is followed by a more enduring market advance that goes on to new highs. Patient investors can not only reap the rewards of those new highs but also take advantage of opportunities to boost their investment performance while waiting for the market to recover through tax-loss harvesting.

How Does Tax-Loss Harvesting Work?

When used deliberately at opportune times, tax-loss harvesting can be an effective strategy for increasing long-term after-tax returns. Tax-loss harvesting involves selling a stock for a loss and using the capital loss to offset any gains or income generated throughout the year for immediate tax savings.

The IRS code allows investors to deduct up to $3,000 of capital losses annually against ordinary income. Ordinary income includes capital gains from stock sales. If you have more than $3,000 in losses, you can carry them forward to future years.

If you still want to own the stock you just sold, you can repurchase it after waiting 31 days to avoid the IRS “wash sale” rule. The rule states that purchasing a stock within 30 days of selling it is considered a wash sale, which disallows the capital loss deduction. You can wait 31 days and repurchase the same stock, but you risk buying it at a higher price, which might make it a less desirable investment.

Alternatively, you can immediately purchase another similar stock but not “substantially identical.” For example, you could sell shares of Facebook and immediately replace them with shares of Amazon, which would not be considered substantially identical. Or you could temporarily replace your Facebook shares with a “proxy” investment, such as a technology ETF, and then sell it after 30 days to repurchase your shares.

How Do Investors Benefit from Tax-Loss Harvesting?

When done in compliance with IRS rules, tax-loss harvesting can provide you with an immediate tax break while allowing you to keep your portfolio intact for the long term. When you eventually sell the stock for a gain, you will be taxed at the more favorable long-term capital gains rate. To that extent, tax-loss harvesting is a tax deferral strategy that can also enhance your portfolio’s long-term performance.

The more you can defer taxes on investments, the better your long-term returns. For example, if, instead of paying the IRS $1,000 in capital gains taxes today, you wait 20 years. Through the power of compounding returns, the difference in value would be substantial. At a compounded rate of return on your investments of 7%, your $1,000 would be worth nearly $4,000 in 20 years. That’s an extra $3,000 you earned on the amount that would have been lost to taxes 20 years earlier.

Beyond tax deferral in your lifetime, you can defer capital gains indefinitely for future generations. Assets passed to your heirs are received on a stepped-up basis at your death, eliminating the capital gains.

Tax-Loss Harvesting as Part of a Sound Investment Strategy

As with any investment strategy, tax-loss harvesting should only be done within your investment objectives. Tax-loss harvesting requires proper timing, a firm grasp of security selection (which to sell and buy), and an understanding of tax implications, so it is essential to work with a financial advisor with experience in portfolio management.

Looking Ahead with Uncommon Cents Investing

Navigating the complexities of the investment world can be challenging, but you don’t have to go it alone. At Uncommon Cents Investing, we’re committed to helping you optimize your financial situation, ensuring that both your short-term tax strategy and long-term investment goals align seamlessly. If you’re seeking expert guidance on strategies like tax-loss harvesting or simply need a partner to help chart the course of your financial journey, we’re here for you. Reach out today, and let’s embark on a path to financial clarity and success together. Schedule a call now.


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More About the Author: Sheena Hanson

Sheena is a highly regarded financial expert known for her clear explanations and practical advice on complex financial matters. She earned her CERTIFIED FINANCIAL PLANNER™️ designation in 2010 and holds a Bachelor of Science degree in Finance from the University of Wisconsin LaCrosse.