Tax Strategies for High Income Earners: The Trial Tax Return

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.

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March 31, 2026
Today is the last day of Women's History Month. And while one month is never enough to capture what women contribute — to finance, to business, to the communities they shape — it is a moment worth honoring before we let it go. At Buttonwood Financial Group, this March has felt particularly meaningful. Not because we needed a designated month to recognize the women on our team, but because it gave us the chance to say out loud what we already know to be true every day: our women make us who we are. Buttonwood is a 15-person boutique wealth management firm based in Midtown Kansas City. Six of those 15 people are women — and they aren't clustered in one place. They lead across every corner of this firm. Our COO manages the operational engine of the business. Our VP of Marketing shapes how Buttonwood communicates with the world. Our Director of Operations keeps everything running with precision. Female representation on our Advisor team brings deep expertise directly to clients' financial futures and support from our accounting team. And our Client Services Specialist is often the first voice clients hear — and one of the most important. In an industry where women have historically been underrepresented, that kind of presence — spanning C-suite, operations, marketing, wealth management, accounting, and client services — doesn't happen by accident. This Is What Intentional Looks Like Wealth management has long been a male-dominated field. Women make up a fraction of financial advisors and senior leaders across the industry. We knew from the beginning that building the team we wanted meant being thoughtful — not waiting for diversity to happen organically, but actively creating an environment where talented women want to stay and grow. We're not perfect, and we're not done. But we're proud of where we are. Beyond Wealth: Women, Wealth & Influence Last year, we launched something we'd been excited about for a long time: Beyond Wealth: Women, Wealth & Influence— a community where women can explore the real intersections of life and money. The response has been remarkable. Women are hungry for this kind of space. One that doesn't talk down to them or assume they need a simplified version of finance — but instead treats them as the intelligent, capable decision-makers they are. We meet, we talk, we learn from each other, and we build the kind of financial confidence that changes lives. Why It Matters in Wealth Management Specifically Women control a growing share of wealth in this country. They often outlive their spouses. They navigate career interruptions. They make major financial decisions every day — and they deserve advisors and firms that truly reflect their experience and understand their full picture. When clients walk through our doors in Midtown Kansas City, they don't just get personalized financial planning. They get a team built to see the whole picture — and that includes the perspective that women bring. Rooted in Kansas City Our commitment to this community runs deep. Through Buttonwood Art Space, our nonprofit arm, we've returned over $1 million to local artists and nonprofits — investing in the creative and cultural fabric of the city we're proud to call home. For us, being a good firm and being a good neighbor have always gone hand in hand. A Word of Gratitude To the women of Buttonwood Financial Group: thank you. The leadership, the care, the rigor, the relationship-building you bring every single day — that's why this firm is as good as it is. And to our clients, partners, and Kansas City community: we're more than 20 years into building something worth celebrating. We're just getting started. Interested in joining Beyond Wealth: Women, Wealth & Influence? Email: info@ButtonwoodFG.com Buttonwood Financial Group is a boutique wealth management firm in Midtown Kansas City with over 20 years of experience in personalized financial planning. Through its nonprofit arm, Buttonwood Art Space, the firm has contributed over $1 million to local artists and nonprofits.
By Jon McGraw March 30, 2026
Geopolitics and economic impacts evolve; and thus, we evolve our investment allocations. Our March rebalance consisted of a series of targeted adjustments designed to keep portfolios aligned with our long-term objectives of producing a more consistent rate of return, while adapting to a changing investment environment. The takeaway is straightforward: we remain firmly invested in growth, but we’re being more intentional about how we are taking risk. The change during this rebalance is a refinement of positioning, not a retreat from our conviction. Staying Invested, With Better Balance We continue to maintain a modest equity overweight, as we believe stocks will still outperform bonds. Our logic reflects an economic macro backdrop that remains supportive. Economic growth has been resilient; earnings have held up, and inflation pressures continue to trend in the right direction. These conditions favor stocks and growth rather than stepping aside. At the same time, the market has begun to reward selectivity over concentration. In response, we trimmed positions that had grown disproportionately large, took profits on recent winners, and reduced some of our most concentrated factor tilts. The goal is not to reduce upside participation, but to pursue it with better diversification and durability. Tempering Regional Bets We made modest regional adjustments to improve balance without changing our core views: U.S. equities: We remain constructive on U.S. earnings power, but trimmed our overweight to the US, after a strong run to reduce concentration risk. Emerging markets: After meaningful gains, particularly tied to AI and semiconductor supply chain, we again took some profits while maintaining meaningful exposure. International developed markets: We reduced, but did not eliminate, our underweight, acknowledging that in a broadening market, extreme regional bets can become less efficient. The result is a more balanced global equity mix, designed to be resilient across a wider range of outcomes. Broadening Our AI Exposure The AI trade has been and continues to remain one of the most powerful long-term themes shaping the global economy. However, the opportunity is not evenly distributed. While many companies are experimenting with AI, only a small subset are successfully deploying it at scale in ways that meaningfully improve productivity and competitiveness. We believe we have strengthened our AI positioning through active investment strategies that seek to identify not only core technology builders, but also early adopters across industries. We have targeted companies that are using AI to create durable advantages rather than simply following the trend: Lessons learned during the .com era. As risks increase and the market becomes more selective, we believe this selective approach matters more than ever. Adding to Defense, with a Global Lens We also added to our exposure to defense stocks, reflecting what we believe is a multiyear, policy driven investment cycle tied to modernization and security priorities. Importantly, we shifted from a U.S. centric approach toward a more diversified global strategy, aiming to capture where defense spending is expanding most clearly. Defense plays a dual role in investment portfolios today: Not only is it a structural growth opportunity; we are also viewing it as a diversifying equity exposure with drivers distinct from traditional economic cycles. An economic recession doesn’t necessarily impact the need for a nation to defend itself. Strengthening Bonds as a Stabilizer Within fixed income, our focus during this rebalance was to improve resilience. Credit spreads are historically tight, meaning investors are being paid very little for taking on credit risk. In these conditions, credit (bonds) can behave more like equity (stocks) during market stress. As such, we reduced credit heavy exposures and added higher quality, longer duration government bonds. The intent is to make our bond allocation a more reliable shock absorber during periods of volatility. At the same time, we would like to preserve the flexibility to add risk later if credit sells off and valuations improve. The Bottom Line Our March 2026 rebalance kept portfolios in our ‘barbell’ structure. Assets are both positioned for growth, which has served us very well, while we continue to increase our defensive positioning. We believe defense has been increased by improving diversification, reducing concentration, and strengthening downside protection.  In short, following our March rebalance, assets are positioned to take advantage of opportunities to participate in an overall economically constructive outlook, but we believe are now better positioned to weather uncertainty with greater resilience. If you have questions about how these changes apply specifically to your cash flows or financial objectives, we welcome the conversation. Thank you for your continued trust and partnership. Important Disclosure This commentary is provided for informational purposes only and reflects general market views as of the date published. It is not intended as investment advice, a recommendation, or a solicitation to buy or sell any security. Asset allocation and diversification do not guarantee profit or protect against loss. Investing involves risk, including the possible loss of principal. Market conditions and investment strategies are subject to change. Please consult with your Buttonwood Financial Group advisor regarding your individual circumstances before making any investment decisions.
February 21, 2026
Tax season has a way of arriving faster than expected. And for 2026, there’s more worth paying attention to than usual—the IRS has updated key figures for tax year 2025, and enforcement around complex returns has intensified. But before you hand everything off to your CPA, a brief pause to review the right details can make the process smoother—and occasionally surfaces something worth acting on. The questions below are starting points for reflection and conversation, not tax guidance. 1. Did anything significant change last year? Life moves fast, and the tax code tries to keep up. A new job, a growing family, a home purchase, a business change, or even a large one-time expense can shift your tax situation in ways that deserve attention. This is also worth thinking about through the lens of your broader advisor team—changes that affect your investments, estate plan, or business interests often have tax consequences that only surface when everyone is looking at the full picture together. If it felt significant, it’s probably worth mentioning. 2. Have you collected all your income documents? Before anything else, make sure the full picture is on the table. W-2s, 1099s, K-1s, Social Security statements, and brokerage summaries should all be accounted for—and reviewed for accuracy, not just collected. A number that looks wrong is worth questioning before your return is filed. One timing note worth flagging: if you hold interests in partnerships, LLCs, private equity funds, or real estate partnerships, K-1s often don’t arrive until mid-March. If your CPA isn’t expecting them, there’s a real risk of filing prematurely without crucial income information 3. Is your paperwork actually ready to hand off? There’s a difference between having your documents and having them organized. A simple folder—digital or physical—sorted by category saves time, reduces back-and-forth with your CPA, and lowers the chance something gets missed in the shuffle. Five minutes of organizing now can prevent a week of delays later. This matters especially if you work with multiple advisors: your wealth manager, CPA, estate attorney, and business attorney each hold pieces of the puzzle. Information that stays siloed between professionals is one of the most common sources of unnecessary complications at filing time. 4. Are your charitable contributions documented? Good intentions don’t substitute for good records. Whether you gave cash, wrote checks, or donated property, make sure you have acknowledgment letters, receipts, or bank records to back it up. For larger contributions, the bar is higher: cash gifts over $250 require written acknowledgment from the charity, non-cash contributions over $500 require Form 8283, and those over $5,000 typically require a qualified appraisal. If you donated appreciated stock or gave through a donor-advised fund, your CPA will also need cost basis information and confirmation of fair market value on the donation date—details that may require coordination with your investment advisor. Timing matters too—gifts need to have been completed by December 31 to count for the prior tax year. 5. Do you have a clear picture of your investment activity? It’s easy to forget about trades made months ago, but we haven't. Sales, exchanges, dividend reinvestments, and distributions can all carry tax consequences. It’s also worth confirming whether any tax-loss harvesting was done on your behalf during the year—those transactions affect your overall gain and loss picture and your CPA should understand them in context. Similarly, if you exercised stock options, received vested restricted stock, or completed a Roth conversion, those activities need to be clearly communicated. Reviewing your year-end statements before you meet with your CPA helps ensure nothing catches anyone off guard. 6. Did your retirement contributions land where you intended? Confirm that what you planned to contribute actually went in—and in the right accounts. If you came up short on IRA contributions, you may still have time to make it right before the filing deadline. If you own a business or have self-employment income, it’s also worth verifying that any retirement plan contributions made through your business are properly coordinated with your personal return. It’s also worth asking whether your current savings rate still fits your retirement timeline. 7. Are your benefit and healthcare accounts squared away? HSAs, FSAs, and similar accounts have their own rules and reporting requirements that are easy to overlook. An HSA withdrawal used for a non-qualified expense, for instance, can trigger a penalty. Pull together your account statements and any related documents so your CPA has the full picture. If you own a business, it’s also worth confirming that health insurance premiums paid through your company are being handled correctly on both your business and personal returns—this is an area where coordination between your bookkeeper and CPA matters more than people expect. 8. What do you want to be more intentional about this year? Tax season is one of the few times most people take a genuine look at their finances. Use that momentum. Beyond filing, consider asking your CPA what your estimated tax payments should look like for 2026, whether any positions on this return carry higher audit risk, and what planning opportunities exist based on what they’re seeing in your return. The IRS has meaningfully intensified enforcement around high-income filers in recent years—particularly around partnership interests, digital asset transactions, and international holdings—so this isn’t a moment to treat compliance as a formality. Whether it’s adjusting your withholding, revisiting your giving strategy, or thinking through a major financial decision ahead, the earlier a conversation starts, the more options you typically have. A Note on 2025 Figures The IRS adjusted several key thresholds for tax year 2025. The standard deduction increased to $15,750 for single filers and $31,500 for married filing jointly, with an additional enhanced deduction of up to $6,000 per qualifying individual age 65 or older ($12,000 for married couples where both spouses qualify). Notably, legislation temporarily increased the cap on state and local tax (SALT) deductions to up to $40,000 for tax years 2025 through 2029 for certain taxpayers who itemize. This expanded cap is subject to income‑based limitations and may phase down for higher‑income filers, meaning the benefit varies significantly based on overall income and deduction profile. As always, whether itemizing or taking the standard deduction makes sense depends on your specific situation and should be reviewed with your CPA. Estate and gift tax exemptions also saw inflationary adjustments for 2025, which may be relevant if wealth‑transfer planning was part of your year. How we can help? We work alongside your CPA—not in place of them. Our role is to help you stay organized, think through priorities, and make sure your financial decisions are working together toward a bigger goal. In our experience, the families who navigate tax season most efficiently are those who proactively connect the pieces across their professional team, rather than assuming the information flows automatically. If it would be helpful to talk through what’s on your plate before you sit down with your tax advisor, we’re glad to do that. Thank you for your continued trust and for allowing us to provide solutions-not just plans. This information is provided for general educational purposes only and should not be considered tax advice. Please consult your tax professional regarding your specific situation
Investmen
By Dale Raimann January 7, 2026
As we closed out 2025, our Investment Policy Committee (IPC) continued its work to refine strategies that balance risk, liquidity, and long-term growth. In our previous update , we shared how the inflation shock of 2022 reshaped our approach to fixed income and led to a more nimble, systematic positioning of bond assets. That proactive discipline remains a cornerstone of our investment process. As we wrapped up 2025, our Investment Policy Committee (IPC) continues efforts to refine strategies that balance risk, liquidity, and long-term growth. With the Fed reducing overnight lending rates for the third time, recent IPC discussions have turned to another critical focus area: cash management. Why Cash Strategy Matters Now With interest rates still elevated and market uncertainty persisting, many investors hold larger-than-usual cash positions. While cash provides stability, it also introduces opportunity cost if left idle. One of our IPC objectives is to ensure that excess cash works harder for you, without compromising liquidity for emergencies or near-term cash needs. Refining Our Cash Allocation Policy For our clients with larger cash needs (generally more than 5% or $50k of liquid assets in cash or money market funds), we are shifting to a proactive T-Bill management strategy, or other suitable investments based on goals and circumstances. For our clients holding less than $50k in cash or money market, we have retained money market for liquidity, but we have made a switch to the default money market fund we are using. Risk and Tax Aware Money Market Selection While yields are similar across money markets today, the underlying investments in each money market fund vary quite a bit. For example, Schwab Prime Money Market (ticker SWVXX) offers a slightly higher yield but invests in asset-backed commercial paper (ABCP), introducing a modest credit risk. In contrast, Schwab Government Money Market (ticker SNVXX), invests primarily in U.S. Treasuries and government-backed securities, making it virtually risk-free and often state income tax-advantaged. With lower risk and only about 10/100’s of 1% yield difference, our IPC has proactively transitioned clients from SWVXX to SNVXX, to prioritize safety and tax efficiency over a marginal yield difference. Connecting Back to Our Broader Strategy These cash management refinements build on the fixed income strategy we recently outlined. By reducing exposure to inflation-sensitive bonds and implementing a more systematic approach, we are positioning portfolios to be more resilient across potentially weaker or higher-rate environments. Optimizing cash allocations and minimizing credit risk within money markets reinforces the same core principle—protecting downside risk while prudently capturing incremental return opportunities. Looking Ahead As we enter 2026, our investment approach remains focused and disciplined. We continue to prioritize liquidity for cash needs, thoughtful risk management, and systematic investment strategies designed to adapt to evolving market and economic conditions. This proactive framework supports long-term portfolio resilience while remaining aligned with your financial objectives. If you have questions about how these updates may impact your investments, cash management, or overall financial plan, we encourage you to connect with your financial advisor at Buttonwood. Our team is committed to delivering personalized wealth management and asset allocation strategies—regardless of market or economic uncertainty. Thank you for your continued trust and for allowing us to coordinate your asset management as part of our Family CFO services.
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As year-end approaches, many clients focus on charitable giving—supporting causes they care about while optimizing their tax strategy. This year carries added urgency: the One Big Beautiful Bill Act (OBBBA) will significantly change charitable giving rules in 2026.

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