How Tax Loss Harvesting Can Potentially Reduce Your Capital Gains Taxes

If you’re like many investors, the thought of paying capital gains taxes on your successful investments might feel overwhelming. But what if there was a strategy to potentially reduce some of those taxes?

It’s called tax loss harvesting, and while the term might sound complicated, it's actually a fairly simple concept that could save you money.

Let’s break it down.

What Is Tax Loss Harvesting?

Think of your investments like a fruit-bearing tree. Some branches, representing your stocks or funds, are heavy with fruit. This symbolizes the gains you’ve made.

But not all branches bear fruit. Some might be bare or even dropping leaves. These represent your underperforming investments or losses.

When you sell a profitable investment (a branch heavy with fruit), you typically have to pay taxes on those gains.

However, here’s where tax loss harvesting comes into play.

If you also sell an underperforming investment at the same time, you can use that loss to offset your gains, potentially reducing the amount of tax you owe.

This is tax loss harvesting in its simplest form.

But before you jump into this strategy, there are a few key rules to understand.

The Wash Sale Rule

One of the most important rules in tax loss harvesting is the wash sale rule.

This rule prevents you from claiming a tax-deductible loss if you buy the same or a ‘substantially identical’ investment within 30 days of selling it.

So, to successfully apply tax loss harvesting, you need to be strategic and avoid buying back the same asset too soon.

Additionally, it’s essential to understand that not all gains are taxed equally.

Long-term gains, those from investments held for more than a year, are generally taxed at a lower rate than short-term gains, which are from investments held for a year or less.

Therefore, aligning your losses with the right type of gains can make a significant difference in your tax savings.

Maximizing Tax Loss Carryforwards

One of the less obvious benefits of tax loss harvesting is that any unused losses can be carried forward to future tax years. If your capital losses exceed your capital gains for a given year, you can apply up to $3,000 of these losses (or $1,500 if married filing separately) to offset regular income, reducing your tax burden even if your capital gains don’t fully match your losses in a particular year. The remaining unused losses are not wasted—they’re carried forward indefinitely until used, creating a strategic reserve that can be tapped as future gains arise.

Keep Your Money Working - Reinvest Smartly

Just because you’re selling a losing investment doesn’t mean your money should sit idle.

A strategy that many investors use is to reinvest the funds into a different, but not identical, asset.

This allows you to keep your money working for you while still taking advantage of the tax loss harvesting benefits.

Timing Matters: Be Proactive Throughout the Year

Many investors wait until year-end to consider tax loss harvesting, but taking a proactive approach can yield better results. By periodically reviewing your portfolio for opportunities to harvest losses throughout the year, you can benefit from tax offsets more consistently. Even as markets generally trend upward over time, investors with diverse portfolios often have different lots of stocks or funds purchased at different times, resulting in various cost bases. As a result, even if a position has gained overall, certain lots within that position might still be eligible for loss harvesting.

Practical Example: Swapping to Maintain Exposure

Let’s say you purchased shares of a stock like NVIDIA (NVDA) that have decreased in value. Instead of holding the loss, you could sell the shares, realizing the loss for tax purposes, and reinvest in a similar—but not identical—asset, like a semiconductor ETF. This allows you to maintain exposure to the semiconductor industry while potentially capturing a tax benefit. It's a strategy to keep your investments aligned with your goals while minimizing tax costs.

Why Tax Loss Harvesting Matters

This strategy can be a powerful way to keep more of your investment returns by lowering the taxes you owe on capital gains.

Depending on how much you have invested and the specific nature of your holdings, tax loss harvesting could save you a significant amount of money each year.

Whether you’re managing a large portfolio or just getting started, tax loss harvesting is one strategy that can help you make the most of your investments.

However, like any financial strategy, it’s important to tailor it to your individual situation.

Building a Tax Loss Reservoir for Major Gains

When applied systematically, tax loss harvesting can build a valuable tax loss carryforward over time. These accumulated losses can be highly advantageous if you’re planning to sell a business, real estate, or other investments with substantial gains in the future. By accumulating losses now, you can offset a significant portion of capital gains taxes later, potentially saving tens of thousands of dollars or more in taxes.

Have Questions? Let’s Chat

If you have any questions about tax loss harvesting or how it might apply to your personal financial situation, I’m here to help.

The information provided in this article is for general educational purposes only and should not be considered as personalized tax advice. While tax loss harvesting can be a valuable strategy, its effectiveness depends on your individual financial situation and tax circumstances. It's important to consult with a qualified tax professional, while a financial professional can work collaboratively with your chosen tax professional to help align your financial goals and investment strategy with your tax planning goals.

This content is developed from sources believed to be providing accurate information. The information provided is not written or intended as tax or legal advice and may not be relied on for purposes of avoiding any Federal tax penalties. Individuals are encouraged to seek advice from their own tax or legal counsel. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel. Neither the information presented nor any opinion expressed constitutes a representation by us of a specific investment or the purchase or sale of any securities. Asset allocation and diversification do not ensure a profit or protect against loss in declining markets.