Arrowroot Family Office
Search
  • Home
  • Services
    • Wealth Management Services
      • Investment Management
      • Individual Retirement Account (IRA)
      • 529 Plan
      • Corporate Retirement Plan
    • Financial Planning Services
      • Equity Compensation
      • Financial Planning
      • Retirement Planning
      • Estate Planning
      • Tax Planning
    • Multi Family Office Services
      • Accounting
      • Tax Efficiency
      • M&A Advisory
      • Wealth Strategy
      • Family Governance
      • Philanthropic Initiatives
    • form

      GUIDELINES TO FINANCIAL FREEDOM

  • Offices
    • Southern California
    • Northern California
    • Michigan
    • Virginia
    • Washington State
  • About
  • Press
  • Contact
  • Client Login
  • BOOK A CALL
BOOK A CALL
  • Home
  • Services
    • Wealth Management Services
      • Investment Management
      • Individual Retirement Account (IRA)
      • 529 Plan
      • Corporate Retirement Plan
    • Financial Planning Services
      • Equity Compensation
      • Financial Planning
      • Retirement Planning
      • Estate Planning
      • Tax Planning
    • Multi Family Office Services
      • Accounting
      • Tax Efficiency
      • M&A Advisory
      • Wealth Strategy
      • Family Governance
      • Philanthropic Initiatives
    • form

      GUIDELINES TO FINANCIAL FREEDOM

  • Offices
    • Southern California
    • Northern California
    • Michigan
    • Virginia
    • Washington State
  • About
  • Press
  • Contact
  • Client Login
  • BOOK A CALL
AFO2023-12-14T09:41:09+00:00

Tax Loss Harvesting: What Is It & How to Use It to Reduce You Tax Bill

Compliance Oversight by:
MCO
MCO Logo

MCO

MyComplianceOffice

A complete compliance management software platform that helps financial services firms unify their activities across conduct and regulatory compliance.

Tax Loss Harvesting: What Is It & How to Use It to Reduce You Tax Bill
Tax Loss Harvesting: What Is It & How to Use It to Reduce You Tax Bill
Tax-loss harvesting is the act of selling securities at a loss to gain back and offset any capital gains tax owed from selling more profitable assets. This is a great strategy commonly used to help limit short-term capital gains, as this type of gain is commonly taxed at a higher rate than long-term capital gains. This tactic is especially helpful in reducing one’s taxes while preserving the value of an investor’s portfolio.
Table of Contents hide
  1. How Tax-Loss Harvesting Works
  2. Maintaining Your Portfolio
  3. Wash-Sale Rule
    1. 1. Tax-Loss Harvesting Only Applies to Investments Held in Taxable Accounts
    2. 2. Tax-Loss Harvesting Does Not Work as Well for Individuals in Lower Tax Brackets
    3. 3. Tax-Loss Harvesting Is Most Useful for Investing in Individual Stocks, Exchange-Traded Funds, or Actively Managed Funds
    4. 4. Understand the Specifics of Tax-Loss Harvesting
    5. 5. Don’t Sell Losses Just to Receive the Tax Break
    6. 6. Put the Cash to Good Use From the Sale
  4. FAQs

How Tax-Loss Harvesting Works

Tax-loss harvesting is also commonly known as tax-loss selling, and investors often use this strategy at the end of the trading year when they assess the annual performance of their portfolio to calculate the impact of their short-term gains capital taxes on their investment portfolio. A short-term investment that shows a loss in value can be sold off to claim a tax credit against investment gains that were sold for a profit.

This can ultimately reduce taxes paid by the investor and help realize significant tax savings. For example, a loss in the value of Security A could be sold to offset and gain back a tax advantage over a gain in value from the sale of Security B.

Maintaining Your Portfolio

Selling a security at a loss can disrupt the balance of one’s portfolio. Tax-loss harvesting allows the investor to carefully construct their portfolio to replace the security or asset that was sold with a similar one to maintain the portfolio’s expected risk, return level, and asset mix. It should be noted that investors should avoid buying the same asset that was just sold at a loss, as that may violate the IRS wash-sale rule.

Helping you achieve your evolving financial objectives

Schedule your advisory call today
Schedule your call now

Wash-Sale Rule

The wash-sale rule dictates that the investor is required to avoid buying the same security that was just sold at a loss for tax-saving purposes. This involves the sale of one security and the purchase of that same security within 30 days of its sale. If the transaction is considered a wash-sale by the IRS, then it cannot be used to offset capital gains tax. This means that investors must not abuse this rule, as IRS regulators can potentially impose strict fines and restrict an investor’s ability to trade certain securities. To not violate any regulations, make sure to follow the following rules to avoid incriminating situations involving short-term gains tax.

1. Tax-Loss Harvesting Only Applies to Investments Held in Taxable Accounts

The concept of tax-loss harvesting is to help offset short-term taxable investment gains. Because the IRS does not tax growth on investments in tax-sheltered accounts such as IRAs, 529s, 401ks, and 403bs, it is important not to apply tax loss harvesting rules on those accounts to remain compliant with the IRS. As long as one’s funds remain within the tax-sheltered account, one’s investments can generate returns without the IRS taxing the funds.

2. Tax-Loss Harvesting Does Not Work as Well for Individuals in Lower Tax Brackets

The idea behind tax-loss harvesting is to help lower one’s tax bill. This means that this rule is most beneficial to those in higher tax brackets as they are typically able to invest more. It can also be said that the higher one’s income tax bracket is, the bigger the savings. For those in lower tax brackets but expect to be in higher tax brackets in the future through promotions or inheritance, it would be best to save tax harvesting strategies to another date when one would be ready to reap the most benefits from this strategy.

3. Tax-Loss Harvesting Is Most Useful for Investing in Individual Stocks, Exchange-Traded Funds, or Actively Managed Funds

Investors who typically invest in index funds often have a difficult time implementing tax-loss harvesting into their portfolio strategy. However, for investors who are indexing exchanged-traded funds, known as ETFs, or mutual funds focusing on a particular niche, that can be a different story, as tax-harvesting works very well for those investments.

4. Understand the Specifics of Tax-Loss Harvesting

The taxes an investor pays on their investment gains are determined by the length of time that investment was bought or held. According to IRS holding-period rules, long-term capital gains tax rates are applied when an investor sells an investment that was held for longer than a year. The IRS rewards this type of financial patience by taxing investors 0%, 15%, or 20% on their gains, depending on their tax bracket. Meanwhile, short-term capital gains tax kicks in when investors sell a security that they have held for a year or less. This gain is taxed as ordinary income, much like one’s wages which often end up having higher tax rates than long-term capital gains tax. The IRS checks one’s investment gains when one files a Schedule D to report their capital gains and losses, so it is important to understand the difference and especially its impact on the amount of taxes that will need to be paid to the IRS.

5. Don’t Sell Losses Just to Receive the Tax Break

One should remember not to become overzealous when exploring tax-loss harvesting options for one’s portfolio. The purpose of investing in securities is to achieve long-term growth that beats the returns of other assets such as bonds, CDs, money market funds, and savings accounts. In exchange for higher returns, investors have to bear the brunt of risk exposure and short-term volatility. Unless there is something fundamentally wrong with the investment that needs to be sold as it has lost its significant value over the course of a year, it is better to hold on to the security and let the magic of time and compound interest smooth out the returns over the future.

6. Put the Cash to Good Use From the Sale

Just as there are immediate benefits of tax-loss harvesting, such as the decrease in capital gains tax, the medium to long-term payoffs are equally as great. Investors who sell securities for a loss now can reinvest their finances into something more attractive or secure depending on any changes in investment strategy. Now that some money has been freed up, one can deploy their finances thoughtfully by using them to rebalance their portfolio if the asset allocation has been altered, invest in a company on one’s watch list, and buy into a mutual fund or ETF that was in one’s radar giving an investor the exposure they are looking for in that asset class or sector that is currently lacking.

That being said, if an investor has a particularly brutal investment year with more total losses than gains, don’t fret: Investors who do not have investment gains to minimize their capital gains tax can still use their losses to offset the taxes paid on their ordinary income and wages. If an investor’s capital loss exceeds more than their total capital gains tax for that year, then they may be eligible to write off up to $3,000 and $1,500 if married but filing separately. If the loss exceeds $3,000, then the remaining amount can be carried over and deducted on tax returns in future years until the entire amount is used up.

FAQs

What is the downside of tax-loss harvesting?
Tax-loss harvesting involves certain risks, including the risk that the new investment purchased from the sale of the losing investment could have higher costs than the original investment and could introduce portfolio tracking errors into the portfolio. There may also be unintended tax implications that are unpredictable.
When should you use tax loss harvesting?
Tax-loss harvesting is only a good idea when the strategy fits in with the overall long-term investment strategy. If one is rebalancing their portfolio to bring it back in line with original investment strategies and with one’s personal risk/reward profile, one may want to sell a losing stock.
How do you take advantage of tax-loss selling?
Tax-loss harvesting is a common strategy investors can use to reduce their capital gains taxes owed from selling profitable investments. A tax-loss harvesting strategy involves selling a losing asset or security at a net loss. One can then use the proceeds from this sale to purchase a similar asset and maintain the overall portfolio balance and risk.
What is the wash sale rule for tax loss harvesting?
If one were to sell a security at a loss and then buy that same or similar security within 30 calendar days before or after the sale, then it would be illegal to take a loss for that security on one’s current-year tax return.
References
  1. https://www.investopedia.com/terms/t/taxgainlossharvesting.asp
  2. https://www.investopedia.com/terms/w/washsalerule.asp
  3. https://www.schwab.com/learn/story/primer-on-wash-sales
  4. https://www.investopedia.com/articles/taxes/08/tax-loss-harvesting.asp
  5. https://www.schwab.com/learn/story/how-to-cut-your-tax-bill-with-tax-loss-harvesting
This material contains opinions of the author, but not necessarily those of Arrowroot Family Office LLC or its subsidiaries. The opinions contained herein are subject to change without notice. Forward looking statements, estimates, and certain information contained herein are based upon proprietary and non-proprietary research and other sources. Information contained herein has been obtained from sources believed to be reliable, but are not assured as to accuracy. No part of this material may be reproduced or referred to in any form, without express written permission of Arrowroot Family Office, LLC. There is neither representation nor warranty as to the current accuracy of, nor liability for, decisions based on such information. Past performance is not indicative of future results.
Family Office, Financial Advisors, Tax Planning

Share this post

Facebook Twitter LinkedIn Email WhatsApp

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *


Related Posts

Trust and Estate Planning: All You Need to Know​
16JanJanuary 16, 2023

Trust and Estate Planning: All You Need to Know

Trust and Estate Planning: All You Need to Know Estate planning is the process of creating a comprehensive plan that designates... read more

Stocks Trade Higher in February as the Rally Broadens Out​
14MarMarch 14, 2024

Stocks Trade Higher in February as the Rally Broadens Out

Stocks Trade Higher in February as the Rally Broadens Out Written by: Rob Santos Rob Santos Chief Executive Officer As CEO and founder of... read more

08NovNovember 8, 2022

How to Choose the Most Suitable Family Office Firm?

How to Choose a Family Office That Is Right Fit for You​ In recent years, the growth and popularity of family... read more

Fiduciary Financial Advisor: What It Is and How to Pick a Right One​
29NovNovember 29, 2023

Fiduciary Financial Advisor: What It Is and How to Pick a Right One

Investing and saving for retirement can be a difficult undertaking, especially when the difficulties of managing the intricacies of life... read more

S&P 500 Registers its Biggest Monthly Gain Since July 2022
02DecDecember 2, 2023

S&P 500 Registers its Biggest Monthly Gain Since July 2022

The big story during November was the decline in Treasury yields. The bond market experienced large moves in interest rates,... read more

29NovNovember 29, 2023

Key Benefits of Year-End Tax Loss Harvesting

In a perfect world, investors would only see gains when checking their accounts. But in the real world, the stock... read more

Discover the Secrets of Financial Freedom​

Learn More

Services

Calculators

Links

Newsletter

  • 4553 Glencoe Ave, Suite 200, Marina del Rey, CA 90292
    (833) 224-2249
  • 2 Boars Head Ln, Suite 110, Charlottesville, VA 22903
    (626) 712-2090
  • 1107 Investment Blvd, Suite 160 El Dorado Hills, CA 95762
    (916) 384-0050
  • 725 Barclay Circle, Suite 215, Rochester Hills, MI 48307
    (248) 453-5252
  • 950 Broadway, Suite M100, Tacoma WA 98402
    (253) 858-2427
  • Investment Management
  • 529 Plan
  • IRA
  • 403(b)
  • 401(k)
  • Corporate retirement
  • Retirement Planning
  • Tax Planning
  • Estate Planning
  • Financial Planning
  • Equity Compensation
  • Traditional IRA Calculator
  • Roth IRA Calculator
  • M&A
  • Arrowroot Capital
  • Join Arrowroot
  • CPA Partnership
  • Press Releases
  • Careers
  • Events
  • Blogs
  • Clients Login
Arrowroot Family Office LLC is a registered investment adviser with the U.S. Securities and Exchange Commission (“SEC”). Registration with the SEC does not constitute an endorsement by the SEC, nor does it imply that AFO has attained a certain level of skill or ability. Content should not be construed as legal or tax advice, AFO is not engaged in the practice of law or accounting.


AFO Form ADV
(Part 2A & Part 2B)

AFO – ADV Part 3
Form CRS

    Terms & Condition | Privacy Policy | Web Accessibility

Copyright © 2025 Arrowroot Family Office – All rights reserved.

Services

Links

  • 4553 Glencoe Ave, Suite 200, Marina del Rey, CA 90292
    (833) 224-2249
  • 2 Boars Head Ln, Suite 110, Charlottesville, VA 22903
    (626) 712-2090
  • 1107 Investment Blvd, Suite 160 El Dorado Hills, CA 95762
    (916) 384-0050
  • 725 Barclay Circle, Suite 215, Rochester Hills, MI 48307
    (248) 453-5252
  • 950 Broadway, Suite M100, Tacoma WA 98402
    (253) 858-2427
  • Investment Management
  • 529 Plan
  • IRA
  • 403(b)
  • 401(k)
  • Corporate retirement
  • Retirement Planning
  • Tax Planning
  • Estate Planning
  • Financial Planning
  • M&A
  • Arrowroot Capital
  • Join Arrowroot
  • CPA Partnership
  • Press Releases
  • Careers
  • Events
  • Blogs
  • Clients Login

Newsletter

Arrowroot Family Office LLC is a registered investment adviser with the U.S. Securities and Exchange Commission (“SEC”). Registration with the SEC does not constitute an endorsement by the SEC, nor does it imply that AFO has attained a certain level of skill or ability. Content should not be construed as legal or tax advice, AFO is not engaged in the practice of law or accounting.


AFO Form ADV (Part 2A & Part 2B)

AFO – ADV Part 3 Form CRS

    Terms & Condition | Privacy Policy | Web Accessibility

Copyright © 2025 Arrowroot Family Office – All rights reserved.

  • 4553 Glencoe Ave, Suite 200, Marina del Rey, CA 90292
    (833) 224-2249
  • 2 Boars Head Ln, Suite 110, Charlottesville, VA 22903
    (626) 712-2090
  • 1107 Investment Blvd, Suite 160 El Dorado Hills, CA 95762
    (916) 384-0050
  • 725 Barclay Circle, Suite 215, Rochester Hills, MI 48307
    (248) 453-5252
  • 950 Broadway, Suite M100, Tacoma WA 98402
    (253) 858-2427

Services

  • Investment Management
  • 529 Plan
  • IRA
  • 403(b)
  • 401(k)
  • Corporate retirement
  • Retirement Planning
  • Tax Planning
  • Estate Planning
  • Financial Planning

Calculators

  • Traditional IRA Calculator
  • Roth IRA Calculator

Links

  • M&A
  • Arrowroot Capital
  • Join Arrowroot
  • CPA Partnership
  • Press Releases
  • Careers
  • Events
  • Blogs
  • Clients Login

Newsletter

Arrowroot Family Office LLC is a registered investment adviser with the U.S. Securities and Exchange Commission (“SEC”). Registration with the SEC does not constitute an endorsement by the SEC, nor does it imply that AFO has attained a certain level of skill or ability. Content should not be construed as legal or tax advice, AFO is not engaged in the practice of law or accounting.

AFO Form ADV (Part 2A & Part 2B)

AFO – ADV Part 3 Form CRS

    Terms & Condition | Privacy Policy | Web Accessibility

Copyright © 2025 Arrowroot Family Office – All rights reserved.

Please note that you are exiting Arrowroot Family Office's website and entering one of a separate company. Arrowroot Family Office does not recommend or confirm any information on this site. Please read all disclosures on Arrowroot Family Office's website and that of the company's page you are about to enter. Continue Cancel