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Harvest Losses. Cut Taxes. Win Smarter.

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Liquidity I How Quickly You Can Turn an Asset into Cash Without Losing Much Value

October 05, 2025

Every investor knows the sting of seeing a portfolio position fall into the red. While no one enjoys a loss, the reality is that downturn and market corrections are part of investing. But what if those red numbers could actually work in your favor? That's where tax-loss harvesting comes in—a strategy that turns investment losses into a potential tax advantage. By carefully selling investments that have lost value, investors can offset capital gains elsewhere in their portfolio and, in many cases, reduce their overall tax bill.

Tax-loss harvesting is not about chasing losses or trying to time the market. Instead, it's about using the tax code wisely, aligning your investment activity with smart financial planning. The approach has become increasingly popular, not only among high-net-worth investors but also with everyday investors who want to be more intentional about their tax strategy.

Understanding the Basics of Tax-Loss Harvesting

This strategy works best in taxable brokerage accounts. Tax-deferred accounts like RAs and 401(k)s don't allow for tax-loss harvesting since gains and losses are not recognized until withdrawal.

  • Selling investments at a loss in a taxable brokerage account can offset realized capital gains and, if losses exceed gains, can reduce up to $3,000 of ordinary income per year, with any additional losses carried forward indefinitely.
  • This strategy is not applicable in tax-advantaged accounts like IRAs or 401(k)s, since gains and losses inside those accounts aren't recognized until withdrawal.
  • The example provided—using an $8,000 loss to offset a $10,000 gain and therefore only being taxed on $2,000—accurately reflects how capital gains and losses net against each other.

The Power of Timing and Rules

While tax-loss harvesting can be powerful, it comes with important rules. One of the most important is the wash-sale rule. This IRS rule prevents investors from selling a security at a loss and then buying back the same, or a substantially identical, security within 30 days before or after the sale. If you do, the loss is disallowed and can't be used to offset gains.

To avoid wash-sale issues, investors often replace the sold investment with a similar—but not identical—asset. For example, if you sell one large-cap U.S. index fund, you might replace it with another large-cap fund that tracks a different index. That way, you stay invested in the market while still capturing the tax benefit.

Timing also plays a role. Many investors harvest losses toward the end of the year, when they have a clearer picture of their capital gains for tax purposes. But tax-loss harvesting isn't limited to December; opportunities can arise anytime market volatility creates sharp downturns.

Benefits Beyond Lower Taxes

At first glance, the primary appeal of tax-loss harvesting is obvious—it reduces your tax liability. But the strategy offers additional benefits as well. By systematically reviewing your portfolio for harvesting opportunities, you're also encouraging disciplined portfolio management. It forces you to regularly assess your investments, rebalance when needed, and avoid letting underperforming positions linger without purpose.

It also offers psychological benefits. Instead of viewing a losing investment purely as a setback, you can reframe it as a tool to improve your financial outcome. That shift in mindset can reduce the emotional sting of losses and reinforce a disciplined, long-term approach to investing.

Potential Drawbacks and Considerations

Despite its advantages, tax-loss harvesting is not without drawbacks. Selling an investment purely for tax reasons may disrupt your overall strategy if not done carefully. You might miss out on future gains if the investment rebounds strongly after you sell. That's why having a replacement strategy—whether it's a similar fund or another asset class—is key.

Another consideration is cost. While tax-loss harvesting can reduce taxes, it may trigger additional transaction fees or management costs, depending on how your portfolio is structured. For some investors, especially those with smaller portfolios, the benefits might be modest compared to the administrative effort.

Finally, the strategy primarily defers taxes—it doesn't erase them completely. While you may offset gains today, if you reinvest and eventually sell at a profit in the future, those gains will still be taxable. The advantage lies in reducing taxes now, potentially investing those savings, and deferring taxes to a later date when you may be in a lower tax bracket.

Who Should Consider Tax-Loss Harvesting?

Tax-loss harvesting is most beneficial for investors in higher tax brackets who regularly realize capital gains. However, it's not just for the wealthy. Any investor with taxable investments and a long-term mindset can benefit from incorporating this into their financial planning.

Situations where tax-loss harvesting may be especially useful include:

  • A year when you realized significant capital gains from selling stocks, bonds, or real estate.
  • A time when you're expecting higher taxable income and want to offset it with capital losses.
  • A volatile market year, when short-term downturns create opportunities to capture losses without significantly altering your overall investment strategy.

For investors in retirement or those systematically drawing down assets, tax-loss harvesting can also be a valuable way to smooth taxable income and preserve more capital for long-term use.

A Long-Term View

It's important to remember that tax-loss harvesting is not a shortcut to building wealth. It is a tax-management tool that works best as part of a comprehensive investment strategy. Used correctly, it complements core investing principles: diversification, asset allocation, and long-term discipline.

Investors should also recognize that the tax code may evolve over time. While current laws allow for unlimited carryforward of unused losses, tax policy is subject to change. That makes it essential to stay informed and, ideally, to consult with a financial advisor or tax professional who can align your investment activity with your broader financial goals.

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No investor likes losses, but the market inevitably dishes them out from time to time. Tax-loss harvesting is a way of turning those setbacks into opportunities. By strategically selling investments at a loss to offset gains, you can potentially reduce your taxable income, improve portfolio discipline, and keep more of your wealth working for you.

As with all tax strategies, the benefits depend on your unique circumstances—your tax bracket, portfolio composition, and long-term financial goals. For some investors, the impact is modest; for others, it can mean thousands of dollars in annual tax savings.

Think of tax-loss harvesting as a silver lining to the natural ups and downs of the market. While you can't control every market move, you can control how you respond to it—and with thoughtful planning, even a loss can help you move closer to your financial goals.

If you're curious about whether tax-loss harvesting could benefit your financial plan, our team is here to help. We'll review your portfolio, explore your tax-saving opportunities, and design a strategy that aligns with your long-term goals. Contact us today to get started on turning potential losses into opportunities for growth.

References

  • [Fidelity: Tax-loss harvesting explained]
  • [Charles Schwab: The wash-sale rule and tax-loss harvesting]
  • [IRS: Topic No. 409 Capital Gains and Losses]

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Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. oXYGen Financial is not affiliated with Kestra IS or Kestra AS. Kestra IS and Kestra AS do not provide tax or legal advice.

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The opinions expressed in this commentary are those of the author and may not necessarily reflect those held by Kestra Investment Services, LLC or Kestra Advisory Services, LLC. This is for general information only and is not intended to provide specific investment advice or recommendations for any individual. It is suggested that you consult your financial professional, attorney, or tax advisor with regard to your individual situation.

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Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. oXYGen Financial is not affiliated with Kestra IS or Kestra AS. Kestra IS and Kestra AS do not provide tax or legal advice. https://Bit.ly/KF-Disclosures

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