Tax loss harvesting is an investment management strategy that improves tax efficiency. It involves selling investments at a loss and using those losses to offset capital gains taxes on other investments. 

Tax loss harvesting is mainly applicable in taxable investment accounts and does not apply to tax-advantaged accounts like IRAs or 401(k)s, where taxes are deferred or exempt.

It’s important to consider the potential long-term impact on your investment strategy and to ensure that the decision to sell is not solely based on tax considerations. Additionally, rules around tax loss harvesting, such as the wash sale rule, can be complex, so consult with a financial advisor or tax professional. Here’s how it typically works:

Step 1: Identification of Underperforming Assets

Identifying underperforming assets is a crucial first step in tax loss harvesting. This involves carefully reviewing your investment portfolio to pinpoint investments that have lost value relative to their purchase price. Here’s a deeper dive into how this process typically unfolds:

Review Portfolio Performance

  • Performance Analysis: Examine the performance of each asset in the portfolio over a specified time frame. This involves looking at the current market value of each investment compared to its cost basis, which is the original value of an asset for tax purposes, usually the purchase price.
  • Asset Comparison: Compare the performance of similar assets within the portfolio or against a relevant benchmark to understand whether the underperformance is asset-specific or part of a broader market trend.

Considerations for Identification

  • Time Horizon: Consider the investment time horizon and whether the asset is expected to recover. Short-term underperformance in a long-term investment might not be a concern, but for tax loss harvesting, the focus is on realizing losses that can offset gains.
  • Asset Allocation: Assess how selling the underperforming asset will affect the overall asset allocation and investment strategy. The goal is to maintain a balanced, diversified portfolio that aligns with your risk tolerance and investment goals.
  • Market Conditions: Consider overall market conditions and specific sector performance. Sometimes, an asset is underperforming due to temporary market downturns or sector-specific issues, which influence the decision to sell now or wait.

Strategic Considerations

  • Wash Sale Rule: Be mindful of the wash sale rule, which prohibits claiming a tax deduction for a security sold at a loss if a substantially identical security is purchased within 30 days before or after the sale. This rule is crucial in deciding which assets to sell.
  • Replacement Assets: Plan for what will replace the sold assets. The idea is to invest in similar (but not substantially identical) assets to maintain your portfolio’s strategic asset allocation without violating the wash sale rule.

Utilizing Technology

  • Many investors use financial software and tools to automate the identification of underperforming assets. These tools can track the cost basis and current value of investments, making it easier to spot which assets are losing money.

The identification process is quantitative and qualitative, involving the numbers and a strategic review of how each asset fits within the broader investment plan. It requires a balance between tax efficiency and adherence to the long-term investment strategy, ensuring that decisions made for tax reasons don’t negatively impact the overall investment goals.

Step 2: Selling the Investments

Selling the investments is the second step in the tax loss harvesting process, where you realize the losses on underperforming assets by selling them. This step is critical because until an investment is sold, any losses or gains are only “unrealized” and have no tax impact. Here’s a detailed look at this phase:

Decision to Sell

  • Strategic Alignment: Confirm that selling the asset aligns with your overall investment strategy and goals. The decision to sell should not be driven solely by tax considerations but should also make sense in the context of your investment plan.
  • Market Timing: Consider the market conditions and timing of the sale. While tax considerations are important, it’s also crucial to consider market dynamics to avoid selling at a significant disadvantage.

Execution of Sale

  • Brokerage Orders: You can place sell orders for the identified underperforming assets through your brokerage account. This can typically be done online or by contacting your broker.
  • Trade Settlement: The trade will need to settle after selling the assets. Trade settlement is the process by which the sale is finalized, and the funds from the sale become available in your account. The standard settlement period for most securities is T+2, which means the transaction is settled two business days after the trade date.

Realizing the Losses

  • Loss Realization: By selling the assets, you convert the losses from “unrealized” to “realized,” which means they can now be used for tax purposes to offset gains or income.
  • Documentation: Ensure that you keep detailed records of the sale, including the date of purchase, sale price, and the realized loss amount. This documentation will be necessary for tax reporting purposes.

Considerations Post-Sale

  • Wash Sale Rule Compliance: Be mindful of the wash sale rule if you plan to reinvest the proceeds from the sale into similar securities. Avoid purchasing substantially identical securities within 30 days before or after the sale to ensure the losses can be used for tax purposes.
  • Reinvestment Strategy: Have a plan for how you will reinvest the proceeds from the sale to maintain your portfolio’s asset allocation and investment strategy. This may involve purchasing similar but not substantially identical securities to replace the ones sold.

Monitoring and Adjustment

  • Portfolio Rebalancing: After selling assets and realizing losses, your portfolio’s asset allocation may have shifted. Evaluate your portfolio to determine if rebalancing is needed to realign with your investment objectives.
  • Continuous Review: Tax loss harvesting is not a one-time activity. Monitor your portfolio for opportunities to harvest losses, especially in volatile markets where asset values fluctuate significantly.

Selling investments as part of tax loss harvesting requires careful consideration and planning. It’s not just about selling but ensuring that every step—from decision-making to execution and post-sale adjustments—aligns with your broader financial and investment strategies.

Step 3: Offsetting Capital Gains

Offsetting capital gains is a central component of the tax loss harvesting strategy, where realized losses from selling underperforming investments are used to reduce the tax liability from capital gains on other investments. This step directly impacts your tax bill by lowering the taxable income from investments. Here’s a closer look at how it works:

Understanding Capital Gains and Losses

  • Capital Gains: These are the profits earned from selling an investment for more than its purchase price. Capital gains are subject to taxes, which can vary based on the holding period of the investment (short-term vs. long-term).
  • Capital Losses: These are the losses incurred when an investment is sold for less than its purchase price. Realized capital losses are what you utilize in tax loss harvesting.

How Offsetting Works

  1. Matching Gains and Losses: The first step is to use your realized losses to offset any realized capital gains. For example, if you have $5,000 in realized capital gains and $3,000 in realized capital losses, you can use the losses to reduce your taxable capital gains to $2,000.
  2. Short-Term vs. Long-Term: It’s important to match short-term losses with short-term gains and long-term losses with long-term gains where possible. This is because short-term and long-term capital gains are taxed at different rates, with short-term gains typically being taxed at a higher rate.
  3. Netting Process: If your capital losses exceed your capital gains, you can use the net loss to offset other types of income, like wages or salaries, up to a specific limit. For example, in the U.S., if you’re left with a net capital loss after offsetting all your capital gains, you can use up to $3,000 ($1,500 if married filing separately) of this loss to offset other income annually, with any remaining losses carried forward to future years.

Considerations in Offsetting

  • Wash Sale Rule: Ensure that the sales you make for tax loss harvesting do not violate the wash sale rule, as this can disallow the losses you intend to use for offsetting gains.
  • Tax Rate Differences: Be mindful of the differences between short-term and long-term gains. Optimizing losses to offset higher-taxed short-term gains can be more beneficial.
  • Carryover Provisions: Understand how loss carryover provisions work in your tax jurisdiction. In many cases, if you can’t use all your capital losses in one year, you can carry them forward to future years, which can help manage your tax burden over time.

Strategy Implementation

  • Year-End Planning: Tax loss harvesting is often most effective when done toward the end of the fiscal year, allowing you to assess your overall capital gains and losses accurately. However, ongoing monitoring is essential as opportunities can arise at any time.
  • Collaboration with Professionals: Working with a tax professional or financial advisor can help ensure that your tax loss harvesting strategy is implemented effectively and complies with tax laws, maximizing its benefits.

Offsetting capital gains through tax loss harvesting can significantly reduce your investment tax liabilities, but it requires careful planning and execution. Ensuring the strategy aligns with your investment goals and tax situation is key to success.

Step 4: Reinvesting

Reinvesting is a critical phase in the tax loss harvesting process, which involves redeploying the proceeds from selling underperforming investments into new positions. This step ensures that your investment strategy remains on course and your portfolio stays aligned with your financial goals and risk tolerance. Here’s a closer examination of the reinvestment process:

Objective Alignment

  • Strategic Consistency: Ensure that new investments align with your overall investment strategy, including asset allocation, risk tolerance, and time horizon. The goal is to maintain the integrity of your investment plan even as specific holdings change.
  • Portfolio Diversification: Choose investments that help maintain or enhance the diversification of your portfolio. Diversification is crucial for managing risk, and any reinvestment should contribute positively.

Avoiding the Wash Sale Rule

  • Substantially Identical Securities: When reinvesting proceeds from a sale, be cautious of the IRS’s wash sale rule, which disallows the deduction of a loss if you purchase a “substantially identical” security 30 days before or after the sale. To comply, select similar securities to maintain your desired exposure but different enough to avoid the wash sale rule.
  • Asset Class and Sector Consideration: If your investment strategy aligns with a different asset class or sector, consider reinvesting in it or choosing a diversified fund (like an ETF or mutual fund) with a different composition but similar market exposure to the sold asset.

Timing and Execution

  • Market Timing: While market timing is generally discouraged, consider the market environment when reinvesting. If the market is particularly volatile, you might temporarily hold the proceeds in cash or cash equivalents. However, being out of the market can also mean missing out on potential gains.
  • Dollar-Cost Averaging: Consider using a dollar-cost averaging approach when reinvesting, especially in volatile markets. This involves investing the proceeds gradually over time to reduce the impact of volatility.

Tax Considerations

  • Tax-Efficient Investments: When selecting new investments, consider their tax efficiency, significantly if you’re investing within a taxable account. For example, some mutual funds and ETFs are designed to minimize taxable distributions.
  • Future Tax Loss Harvesting Opportunities: When selecting new investments, consider the potential for future tax loss harvesting. Diversifying among assets with different risk/return profiles can provide more opportunities for tax loss harvesting in the future.

Long-Term Focus

  • Review and Adjust: Regularly review the new investments as part of your broader portfolio to ensure they continue to meet your investment objectives. Be prepared to adjust as necessary in response to changes in your financial goals or market conditions.
  • Continuous Monitoring: Stay engaged with your portfolio, looking for further tax loss harvesting opportunities or the need to rebalance.

Reinvesting thoughtfully after-tax loss harvesting is essential for maintaining investment momentum and working towards your financial objectives. It requires balancing tax strategy, market conditions, and your overarching investment philosophy.

Step 5: Carrying Over Excess Losses

Carrying over excess losses is an essential aspect of tax loss harvesting that comes into play when your realized capital losses exceed your realized capital gains for the year. In such cases, the tax code in many jurisdictions, including the United States, allows investors to use the excess losses in several beneficial ways. Here’s how it works in more detail:

Offset Other Income

  • In the year you realize more losses than gains, you can typically use a portion of the net loss to offset other types of income, such as wages, salaries, or business income. For example, in the U.S., the IRS allows individuals to deduct up to $3,000 ($1,500 if married filing separately) of net capital losses against other types of income annually.

Loss Carryover

  • Any net losses that exceed the annual limit for offsetting other income can be carried forward to future tax years. This carryover has no expiration; you can continue to carry forward unused losses indefinitely until they’re fully utilized.

How Loss Carryover Works

  1. Carryover to Offset Future Gains: In subsequent years, you can use carried-over losses to offset capital gains. This can be particularly useful in years when your investments perform well and you realize significant capital gains.
  2. Annual Deduction Against Ordinary Income: If you still have more losses carried over in a future year than gains, you can continue to deduct up to the annual limit (e.g., $3,000 for individuals) against ordinary income. This process can continue each year until all carried-over losses are used up.

Strategic Considerations

  • Tax Planning: When using carried-over losses, consider your broader tax situation. In some years, it might be more advantageous to use losses to offset ordinary income, often taxed more than long-term capital gains.
  • Investment Strategy Alignment: Ensure that decisions about realizing losses, carrying over excess losses, and offsetting gains or income align with your overall investment strategy and financial goals. Don’t let tax considerations dictate entirely your investment decisions.
  • Record Keeping: Maintain meticulous records of your realized losses, the amount used to offset gains and income each year, and the amount carried over. Accurate record-keeping is essential for compliance and making informed decisions in future tax years.

Practical Application

  • Use with Future Tax Loss Harvesting: As you monitor your portfolio for tax loss harvesting opportunities in future years, consider how carried-over losses can complement new harvesting opportunities to optimize your tax situation.

Carrying over excess losses provides a valuable tool for managing your tax liability over multiple years, offering a silver lining when part of your portfolio underperforms. It’s a strategic element of tax loss harvesting that can contribute to your financial efficiency and long-term investment success.