Preparing a strategy that is both advantageous and tax-efficient might feel daunting at first. Thankfully, there are some tax strategies for high income earners you can do now to keep from overpaying this tax season.

Build Your Team of Professionals

You might build a team for any number of pursuits, from organizing a baseball team to putting together people to run a business. Any team is not only an organization of people, but also a combination of talents.

Building a financial team to tackle your taxes may often mean talking to more than one person. Your trusted financial professional can speak to a wide range of financial issues, but they may want to consult others who have specialized training. At Buttonwood, we strategize with many tax professionals allowing us to pair their expertise directly with our client’s needs.

Trial Tax Return

We recommend doing a trial tax return before year-end to assess your tax implications, thus allowing for current year action to maximize tax opportunities.

At Buttonwood, this process starts by duplicating 2020 tax return data and updating the data for 2021. To obtain updates, run reports via a financial planning portal. Focus on taxable account gains, losses, dividends, and interest. In addition, update changes to social security and 1099 income. Finally, run a P&L via your accounting software for business entities to complete Schedule C, E or F. Details from these reports can be provided to your CPA for a more accurate view of your 2021 tax liability. This leaves time in the current year to proactively manage your tax bill. If you don’t have a financial planning portal or accounting software, we do and are here to assist.

If you may find you had a lower income year in 2021. If that is the case, you could create additional income to fill up lower tax brackets for 2021; a strategy we strongly recommend. This could be done through a Roth conversion.

If your income was higher in 2021, can reduce your income by adding to retirement plans, making large business purchases this year for depreciation, making charitable contributions, opting for an elective medical procedure, etc. If you had a liquidity event in 2021, we recommend utilizing a donor advised fund.

By doing a trial tax return, you may find some key tax strategies for high income earners. Contact us today if you would like to explore existing strategies.

Tax-Focused Investment Strategies

Once you have the right team of financial professionals who understand your financial situation, there are some investment strategies you may want to consider.

Backdoor Roth IRA

With income over $400k, this strategy is on the chopping block with Biden administrations recent tax proposal. However, for now, if you are a high earner with an income above the IRS’s income limit for Roth IRA accounts, you may have the option to create a backdoor Roth IRA. Just as it sounds, this option allows high earners to bypass the income limits and still utilize the tax advantages of a Roth IRA account.

To create a backdoor Roth IRA, you’ll need to:

  1. Open and contribute to a traditional IRA.
  2. Convert your traditional IRA to a Roth IRA account (your account administrator will provide the necessary paperwork and instructions to do this).
  3. Once tax season rolls around, pay taxes on the contributions (essentially you’re paying back the tax deduction you received when initially contributing to your traditional IRA).
  4. Pay taxes on any additional gains your traditional IRA account may have made over time.

A backdoor Roth IRA may be beneficial for those whose income level is above the ceiling limit set by the IRS. Additionally, it’s important to remember that Roth IRAs do not have required minimum distributions (RMD’s), only traditional IRAs do.

When considering a backdoor IRA, or Roth conversion, evaluate the tax obligations you might pay today versus the tax benefits you may realize toward retirement.

Tax-Focused Gifting

Smart moves can help you manage your taxable income and taxable estate. For instance, if you’re making a charitable gift, giving appreciated securities that you have held for at least a year is one choice to consider. In addition to a potential tax deduction for the fair market value of the asset in the year of the donation, the charity may be able to sell the stock later without triggering capital gains.

The annual gift tax exclusion provides a way to remove assets from your taxable estate. You may give up to $15,000 ($30,000 if you are married) to as many individuals as you wish without paying federal gift tax, so long as your total gifts keep you within the lifetime estate and gift tax exemption of $11.7 million for 2021. 1

Retirement Plan Funding

The more you can shelter, the more complex the rules. Defined Benefit, Define Contribution, Self-employed 401(k), SEP and SIMPLE Retirement plans are all examples of options where contributions can reduce your taxable income.

Tax-Loss Harvesting

Tax-loss harvesting refers to the practice of taking capital losses (you sell securities worth less than what you first paid for them) to help offset the capital gains you may have recognized. While this doesn’t get rid of your losses, it can be an effective approach to manage your tax liability.

Up to $3,000 of capital losses in excess of capital gains can be deducted annually, and any remaining capital losses above that can be carried forward to, potentially, offset capital gains next year. 2  But remember, tax rules are constantly changing, and 2022 is shaping up to look different than 2021!

By taking losses this year and carrying over the excess losses into the next, you can potentially offset some (or maybe all) of your capital gains next year. Before moving ahead with a trade, it’s important to understand the role each investment plays in your portfolio.

If you’re looking into this strategy, familiarize yourself with the IRS’s “wash-sale rule.” This rule indicates that investors can’t claim a loss on a security if you buy the same or a “substantially identical” security within 30 days before or after the sale. 2

With these strategies in mind, there are things you may be able to do in 2021 to address both your current tax obligation and those you may be required to address further down the road. We know this can be a lot to digest, and even more to actually implement. Our team stands ready to assist and implement tax strategies for high income earners and more. Contact us today to get started.

Managing through these strategies can involve a complex set of tax rules and regulations. This discussion of tax-focused giving is for informational purposes only and is not a replacement for real-life advice, so make sure to consult your financial, tax, and legal professionals before modifying your gifting strategy.
Keep in mind that the return and principal value of securities will fluctuate as market conditions change and past performance is no guarantee of future returns.
This content is developed from sources believed to be providing accurate information. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. The opinions expressed and material provided are for general information, and should not be considered a solicitation for the purchase or sale of any security.

Recent Buttonwood Articles


Estate planning documents representing family, legacy, and financial planning.
By Danielle Brown MSF, CFP® • September 28, 2026
The 2026 federal estate tax exclusion is $15 million per individual. Learn why being under the threshold does not make estate planning irrelevant.
Buttonwood Financial Group Investment Policy Committee May and June 2026 portfolio rebalance summary
By Jon McGraw, Investment Policy Committee Chair, Buttonwood Financial Group (Kansas City) • July 20, 2026
How our Investment Policy Committee approached the May & June 2026 rebalances: trimming equity risk, upgrading bond quality, and adding liquid alternatives.
Child placing coins into a piggy bank while learning about saving and financial responsibility.
By Danielle Brown, CFP MSF • July 7, 2026
What families should know about Trump Accounts eligibility, contributions, financial literacy. Child investment accounts may fit in broader financial plan.
By Jon McGraw • July 1, 2026
Beyond fees, DIY investing carries hidden costs — time, taxes, and coordination. A Kansas City wealth management perspective on when self-directed makes sense
SpaceX and Anthropic are filing for the two largest IPOs in history. Learn how index fund exposure,
By Kristy Wieland • June 10, 2026
SpaceX and Anthropic are filing for the 2 largest IPOs in history. Index fund exposure, 401(k) passive buying, and mutual fund holdings mean you may already own them
By Kristy Wieland • May 16, 2026
The Buttonwood Agreement: Where American Finance Took Root — and Why Our Name Exists The Buttonwood Agreement was a compact signed on May 17, 1792, by 24 stockbrokers and merchants beneath a buttonwood tree at 68 Wall Street in New York City. It established the rules of organized securities trading in America and laid the foundation for what would become the New York Stock Exchange. Buttonwood Financial Group takes its name directly from this founding moment; as a daily commitment to the integrity, transparency, and long-term thinking those original brokers put on paper. What was the Buttonwood Agreement, and why it still matters The Buttonwood Agreement came at a moment of crisis. The Panic of 1792, America's first speculative bubble and market collapse, had shattered public confidence in capital markets. Prominent financiers defaulted. Prices fell. Investors panicked. Alexander Hamilton worked to stabilize the system, but the lasting fix came from the professionals themselves. On May 17, 1792, 24 brokers gathered under a buttonwood (sycamore) tree outside 68 Wall Street and signed a two-sentence agreement: they would deal only with each other, charge a standard commission of one-quarter percent, and give preference to fellow signers in all negotiations. Simple. But the effect was transformative. By agreeing to hold a higher standard collectively, they rebuilt confidence in the market itself. The Buttonwood Agreement is widely regarded as the founding document of the New York Stock Exchange and of organized American finance. Why Buttonwood Financial Group carries this name Boutique wealth management firms are built on process and trust. When we named our firm Buttonwood Financial Group, the choice wasn't aesthetic; it was philosophical. Our name is a daily accountability measure; a reminder that the values those brokers signed onto in 1792 — integrity, structure, and responsibility — are exactly the values our clients deserve today. The families and individuals we serve aren't looking for surface answers and financial products. They're looking for an experienced team that has been tested across market conditions, that communicates honestly, and that approaches every client relationship from a fiduciary capacity in a long-term commitment. That's what an established boutique wealth management firm looks like in practice. What experience really means Experience in this industry isn't about credentials alone. It means you have been present with clients through market downturns and periods of uncertainty. You have worked alongside families through estate complexity, business transitions, and inheritance conversations. You have coordinated tax strategy, cash flows, and generational goals at the same time; because for most families, those things can't be separated. Our Team brings that depth to every engagement. Not because we're proud of our tenure, but because the people we serve deserve to work with real people whose judgment has been informed by real world complexity and a wide range of client circumstances. The values that haven't changed in 234 years The Buttonwood Agreement was forged in a crisis to restore confidence. That context mirrors what many clients feel when they first reach out to a firm like Buttonwood. The financial world is complex, opaque, and hard to navigate. Our commitment is to bring transparency, fiduciary responsibility, and honest communication to every relationship, the same values those brokers enshrined in 1792. Roots matter. They tell you where a firm stands when things get hard. On Buttonwood Agreement Day, we honor that founding moment, and recommit to carrying it forward. Connect with Buttonwood Financial Group If you're evaluating whether your current wealth management relationship reflects these values, we'd welcome the conversation. Our advisors work with individuals, families, and business owners on comprehensive, fiduciary-driven financial plans built around your long-term goals. Frequently Asked Questions What is the Buttonwood Agreement? The Buttonwood Agreement was a compact signed on May 17, 1792, by 24 stockbrokers and merchants in New York City. It established standardized rules for securities trading, dealing only among members, and charging a fixed commission. It is considered the founding document of the New York Stock Exchange. When is Buttonwood Agreement Day? Buttonwood Agreement Day is observed annually on May 17, marking the date the original agreement was signed in 1792 outside 68 Wall Street in New York City. Why is the Buttonwood Agreement significant in finance? The Buttonwood Agreement replaced chaotic, unregulated securities auctions with a system of structured, trust-based trading. It restored public confidence after the Panic of 1792 and established the foundational principles, integrity, accountability, and standardized commissions, that governed Wall Street for nearly two centuries. What does Buttonwood Financial Group do? Buttonwood Financial Group is an independent SEC Registered Investment Adviser. A boutique wealth management firm. The firm works with individuals, families, and business owners to provide both financial planning and investment management services. By serving as the primary financial advisor and administrator, Buttonwood is essentially acting as the family's "CFO" while the client remains as the family "CEO." Buttonwood strives to organize, formalize, implement, and monitor financial strategies consistent with clients' multi-generational goals and objectives. What makes a boutique wealth management firm different? Boutique wealth management firms typically offer more personalized service, deeper advisor relationships, and a fiduciary-first approach. Advisors and their support teams generally work with fewer clients and provide more integrated guidance and may reach a deeper level of strategy across investments, tax, business and estate planning, and financial planning. How do I choose an experienced financial advisor? We often see the following criteria: Look for advisors with a fiduciary obligation, verifiable credentials (CFP, CFA, or similar), a transparent fee structure, and experience working with clients whose situations are similar to your own. Confirm the advisor's registration status at adviserinfo.sec.gov. B uttonwood Financial Group is a registered investment adviser. The information provided in this article is for general informational purposes only and does not constitute investment, financial, tax, or legal advice. Past results are not indicative of future performance. All investing involves risk, including possible loss of principal. Please consult a qualified professional for advice specific to your situation.

Are you ready to explore the benefits of your very own Family CFO?

LET'S TALK

Buttonwood Services


About Buttonwood Financial Group