Year End Tax Strategies – 2021

Near the end of each year, we proactively review opportunities for year end tax strategies through the lens of a trial tax return. Our objective is to surface strategy for tax management of your financial life. Each family we work with has unique situations. However, each discussion starts around looking at your income and  which tax bracket  you will fall into. Remember to review for both Federal and State rates.

The following list is a summary of some of the more common strategies we implement. As a disclaimer, please know the information contained is not tax advice and we strongly recommend taxpayers consult with their tax advisor when making tax and financial decisions.

Take advantage of opportunities:

  • Fully fund IRA / Roth to IRS limits. If income is high, fund an IRA, report as a non-deductible contribution and backdoor Roth convert if possible
  • If Self Employed, fully fund 401(k) ( $64,500 in 2021  for those age 50+)
    • Include: 1) Employee Pretax, 2) Employer Profit Share and 3) Employee Post Tax
  • Tax loss ‘harvest’ your investments to re-set your basis and remove future tax. Sell investments that may have declined in value and use losses to offset gains.
  • Rather than giving cash, gift appreciated assets to charity
  • Gift assets to family to take advantage of the  large unified credit limits  or take advantage of the $15,000 annual gift tax exclusion amount.
  • Review your medical plan for an option that allows for a  Health Savings Account (HSA). Funding and growing assets in an HSA can open the door for retirement before age 65 (when Medicare starts).
  • If you are involved with an Irrevocable Trust, review distributing income out of the trust to the trust beneficiaries to reduce the tax rates from the ‘estate’ tax table to individual tax rates. This is  commonly known as the 65 day rule.
  • If you have a business or started a side gig this year:
    • Even very small businesses can deduct ‘ business expenses ’ like home-office deduction, write-offs for mileage and materials and equipment.
    • If you have a business close to break even, create a loss by pushing receivables out to 2022, prepaying expenditures in 2021 and maximizing bonus depreciation.
    • Use bonus depreciation to create a larger NOL. Unlike a Section 179 deduction, bonus depreciation will create a larger NOL.

Increase Income to “fill up” lower tax brackets:

If you took the year off and income is low

  • Implement a Roth conversion by moving IRA assets to your Roth. This creates a tax impact today, but will remove assets from future taxation.
  • If Self Employed, invoice clients in advance for services for next year. Incentivize through a ‘prepayment’ discount / package.
  • The lowest tax brackets have a 0% capital gain tax rate so sell appreciated assets and recognize the gain. If there is a stock with a big gain you still want to own, simply sell and re-purchase the shares.

Decrease income to “drop” to lower tax brackets:

  • Increase retirement plan contributions. If cash flow doesn’t allow for full 401(k) plan contributions and you have non-retirement assets on the balance sheet, increase 401(k) by $1 and take $1 out of savings to live.
  • Make a gift to charity. At the very least,  give $300 to charity  and receive a tax deduction – even if you don’t itemize. A larger gift in a high income year allows for the creation of a ‘lifetime giving account.’ Charity can be an actual non-profit organization or it can be your own ‘ donor advised fund ’ , ‘private family foundation’, ‘ charitable gift annuity’  or other option. If you have appreciated assets, remove the capital gains tax and gift these assets directly to the charity ‘in-kind’.
  • Take advantage of Qualified Charitable Distributions (QCDs). If you are over age 70.5 you can directly gift up to $100,000 per year from your retirement accounts to charity using QCDs.
  • If you’re on the itemize-or-not borderline, your year-end strategy could focus on timing of charitable gifts and expenses to pull multiple years of gifts / expenses into a single year. The goal is to surpass the standard-deduction amount and claim a larger write-off. If you itemize, lump medical expenses, charitable gifts, state income taxes, payments for long term care policies, etc. into a single year. Use this opportunity to gift things you are no longer using,  receive a tax deduction , and allow others to enjoy them.
  • If Self Employed, pay current year invoices as well as invoices for costs coming next year. Also, review delaying billing of clients until late December so you won’t receive payment until the next year.
  • If kids, grandkids, extended family are in, or will be going, to school:
    • Contribute to a  529 Plan  for possible state tax deduction
    • Prepay tuition to take advantage of the American Opportunity Tax Credit, which you can take for students who are in their first four years of undergraduate study, is worth up to $2,500 for each qualifying student. Married couples filing jointly with modified adjusted joint income of up to $160,000 can claim the full credit; those with MAGI of up to $180,000 can claim a partial amount.
  • Likewise, if you’re planning to take a class next year to boost your own career, consider prepaying the January bill before December 31 so you can claim the Lifetime Learning Credit on your 2021 tax return. The credit is worth up to 20% of your out-of-pocket costs for tuition, fees and books, up to a maximum of $2,000. It’s not limited to undergraduate expenses, and you don’t have to be a full-time student. Married couples filing jointly with MAGI of up to $118,000 can claim the full credit; those with MAGI of up to $138,000 can claim a partial credit.
  • If someone is disabled or has a ‘special needs’ situation, review an ABLE  account. Contributions up to $15,000 a year to an ABLE account, allow people with qualifying disabilities to save money without jeopardizing government benefits (ABLE account beneficiaries can contribute more to their own account). You don’t have to invest in your own state’s plan, but if you are a resident of one of the states that do offer a tax break for ABLE accounts, you can likely deduct your contribution.
  • If you are interested in alternative energy, a nonrefundable tax credit is available for qualified solar electric property, qualified solar water heating property, qualified fuel cell property, qualified small wind energy property, and geothermal heat pump property. Cooperative and condominium dwellers can claim the credit by splitting the cost of installing equipment with other unit owners. The credit is 26 percent of the cost of eligible property placed in service in 2020-2022; and 22 percent of the cost of eligible property placed in service in 2023. There is also a $500 credit limit with respect to each 0.5 kilowatts of capacity of qualified fuel cell property expenditures for each tax year.

Prevent surprises:

  • If income has changed materially throughout the year,  review withholding tables  to make sure there isn’t too little / too much being withheld
  • Flexible spending accounts (FSA) are subject to a “use it or lose it” rule. Check to see if your employer has adopted a grace period permitted by the IRS, allowing employees to spend 2021 set-aside money as late as March 15, 2022. If not, you can do what employees have always done and make a last-minute trip to the drug store, dentist or optometrist to use up the funds in your account.

Buttonwood Financial Group serves as multigenerational Family CFO, working with you, as the CEO of your family to uncover and maximize opportunities for tax planning, investments, cash flows and more. If you are in need of year end tax strategies and a holistic financial plan,  contact us today  to learn how our Family CFO services can benefit you.

Recent Buttonwood Articles


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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December 23, 2025
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December 12, 2025
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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