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.
The post Year End Tax Strategies – 2021 appeared first on Buttonwood Financial Group, LLC.
Recent Buttonwood Articles
The 2026 federal estate tax exclusion is $15 million per individual. Learn why being under the threshold does not make estate planning irrelevant.
How our Investment Policy Committee approached the May & June 2026 rebalances: trimming equity risk, upgrading bond quality, and adding liquid alternatives.
What families should know about Trump Accounts eligibility, contributions, financial literacy. Child investment accounts may fit in broader financial plan.
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 2 largest IPOs in history. Index fund exposure, 401(k) passive buying, and mutual fund holdings mean you may already own them
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?
