Unlock Tax Efficiency in Your Portfolio

This guide provides an interactive exploration of tax-loss harvesting (TLH), a powerful strategy to potentially lower your investment tax bill. We'll break down the concept, demonstrate its application, and let you simulate its impact.

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What is It?

TLH is the practice of selling an investment at a loss to offset taxes on both capital gains and, to a limited extent, ordinary income.

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The Goal

The primary goal isn't to realize losses, but to create a valuable tax asset that can reduce your tax liability while maintaining your desired market exposure.

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Key Benefit

It turns market downturns into opportunities for tax savings, enhancing your portfolio's after-tax returns over the long term.

The Tax-Loss Harvesting Process

Understanding the TLH workflow is key to implementing it effectively. This section visually breaks down the strategy into four distinct steps. Hover over each step to see more details about what's involved and why it's important for the overall process.

Step 1

Sell Losing Investment

Identify and sell a security in your taxable portfolio that has an unrealized loss.

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Step 2

Realize Capital Loss

The sale "harvests" the loss, making it official for tax purposes. This loss is now a tax asset.

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Step 3

Offset Gains/Income

Use the harvested loss to offset capital gains elsewhere. Up to $3,000 can offset ordinary income annually.

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Step 4

Reinvest & Stay Exposed

Reinvest the proceeds into a similar (but not "substantially identical") asset to maintain market exposure.

Strategies and Replacement Assets

Effective tax-loss harvesting requires a smart approach to both timing and reinvestment. This section explores different strategies and provides an interactive tool to help you think about suitable replacement investments without triggering a wash sale.

Choosing a Reinvestment

After selling a security for a loss, you must reinvest in an asset that is not "substantially identical" to avoid the Wash Sale Rule. Select a sold asset type below to see potential replacement strategies.

Your replacement suggestions will appear here.

Common TLH Approaches

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    Year-End Harvesting

    The traditional approach, where investors review their portfolios in November or December to find harvesting opportunities before the tax year closes.

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    Opportunistic (Year-Round)

    A more active strategy. Investors or automated services monitor for harvesting opportunities throughout the year, especially during periods of market volatility.

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    Threshold-Based

    Selling is automatically triggered when a position drops by a predetermined percentage (e.g., 5%). This is a systematic, data-driven approach often used by robo-advisors.

Advantages, Disadvantages & Rules

Tax-loss harvesting offers significant benefits, but it's not without its complexities and potential downsides. Here, we compare the pros and cons and explain the most critical regulation: the Wash Sale Rule.

Advantages

  • Reduces Taxable Income: Directly lowers your tax bill by offsetting gains and up to $3,000 of ordinary income.
  • Improves After-Tax Returns: By deferring taxes, you keep more of your money invested and compounding over time.
  • Tax Rate Arbitrage: Can be used to offset short-term gains (taxed at higher rates) with losses.
  • Portfolio Rebalancing: Provides a tax-efficient reason to exit a losing position and re-evaluate your allocation.

Disadvantages

  • It's a Deferral, Not Elimination: You lower your cost basis in the new investment, potentially leading to higher capital gains when you eventually sell.
  • Transaction Costs: Frequent trading can incur commission fees or bid-ask spreads that may erode the tax benefit.
  • Wash Sale Rule Risk: Violating this rule (explained below) negates the tax loss, making the strategy ineffective.
  • Tracking Complexity: Can be difficult to manage manually across multiple accounts.

The Wash Sale Rule Explained

The IRS prohibits you from claiming a loss on a security if you buy a "substantially identical" security within 30 days before or 30 days after the sale (a 61-day window). This prevents investors from selling a stock to claim a loss, only to immediately buy it back.

Example: You sell 100 shares of XYZ stock for a loss on June 15th. You cannot claim that loss for tax purposes if you bought any XYZ shares between May 16th and July 15th. The rule also applies to options on the stock and to substantially identical securities like certain ETFs from different providers tracking the exact same custom, narrow index.

Simulate Your Tax Savings

Curious about the potential impact on your own portfolio? Use this interactive calculator to estimate the tax savings from a hypothetical tax-loss harvesting scenario. Enter your own figures to see how harvesting a loss could reduce your tax liability.

Scenario Inputs

Estimated Results

Results will appear here after calculation.