End Of Year Tax Loss Harvesting Strategies

Thayer Partners Thayer Partners December 04, 2025

Unlock the power of tax loss harvesting to optimize your investment portfolio and minimize your tax burden before the year ends.

Maximizing Investment Returns Through Smart Tax Planning

End-of-year tax loss harvesting is a sophisticated tax strategy that enables business owners and executives to strategically offset capital gains and reduce overall tax liability. By selling underperforming investments at a loss, you can effectively counterbalance gains realized elsewhere in your portfolio, leading to a more efficient after-tax return.

Savvy tax planning doesn’t just focus on maximizing returns, but also on minimizing unnecessary tax exposure. This dual approach allows you to preserve more capital for reinvestment and compounding, aligning with long-term wealth-building objectives.

Identifying Eligible Assets for Tax Loss Harvesting

Not all assets in your portfolio are suitable candidates for tax loss harvesting. Typically, securities such as stocks, mutual funds, and ETFs held in taxable accounts are eligible, while assets in tax-advantaged accounts like IRAs and 401(k)s do not qualify. It is important to review your investment holdings for positions that have declined in value since purchase and determine whether a sale aligns with your overall portfolio strategy.

Careful selection ensures that you are not only realizing losses for the current year but also maintaining a well-diversified investment mix post-harvest. Working with your financial advisor to identify loss positions that won't disrupt your long-term objectives is essential.

Avoiding Common Tax Traps and Wash Sale Rules

A critical pitfall to avoid during tax loss harvesting is violating the IRS wash sale rule, which disallows a loss deduction if you purchase the same or a "substantially identical" security within 30 days before or after the sale. Violating this rule can negate the tax benefits you intended to capture.

Additionally, be mindful of other tax traps, such as inadvertently triggering short-term capital gains or not considering the impact on future portfolio income. Strategic documentation and timing of your trades can help you sidestep these common errors and protect the integrity of your tax strategy.

Strategic Timing: When to Harvest Losses for Maximum Benefit

Timing is everything when it comes to maximizing the benefits of tax loss harvesting. While year-end is a common period for this activity, periodic portfolio reviews throughout the year can uncover opportunities to realize losses without waiting until December. This proactive approach allows you to better manage market volatility and avoid the last-minute rush that could lead to missed deadlines.

It’s crucial to complete all sales by December 31st to have losses count against the current year’s gains. Setting up a process to regularly monitor your portfolio positions and tax implications can ensure you don’t miss key deadlines and opportunities.

Integrating Tax Loss Strategies into Your Long-Term Financial Plan

Tax loss harvesting should be viewed as one tool within a broader, long-term financial framework. Coordinating this strategy with other elements—such as portfolio re-balancing, income planning, and succession objectives—ensures your efforts are cohesive and sustainable over time.

By embedding tax loss harvesting into your annual financial review, you can build a more resilient investment strategy that adapts to market conditions while optimizing your after-tax wealth accumulation. Engaging with a tax or investment professional can help ensure that your strategies are aligned with both your immediate needs and long-term goals.

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This material prepared by Thayer Partners is for informational purposes only.  It is not intended to serve as a substitute for personalized investment advice or as a recommendation or solicitation of any particular security, strategy or investment product.  Thayer Partners is a Registered Investment Adviser. SEC Registration does not constitute an endorsement of Thayer Partners by the SEC nor does it indicate that Thayer Partners has attained a particular level of skill or ability. The material has been gathered from sources believed to be reliable, however Thayer Partners cannot guarantee the accuracy or completeness of such information, and certain information presented here may have been condensed or summarized from its original source.  Thayer Partners does not provide tax or legal or accounting advice, and nothing contained in these materials should be taken as such.

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