10 Year-End Tax Strategies for Affluent Families 

By Brett Gottlieb 

For families with significant assets, year-end tax planning often involves more than finding a few additional deductions. Investment gains, charitable giving, retirement distributions, equity compensation, and estate planning decisions can all affect your tax situation, and several of those decisions need to be made before December 31.

That makes the final months of the year a good time to look across your finances and identify opportunities while you still have time to act. Here are 10 year-end tax strategies to consider before 2026 comes to a close.

1. Review Capital Gains and Losses Across Your Portfolio

If you realized significant capital gains this year, review your taxable investment accounts for losses that could offset some of those gains. Capital losses generally offset capital gains, and if your losses exceed your gains, up to $3,000 may be used to offset ordinary income. Additional losses can generally be carried forward to future tax years.

Tax-loss harvesting should still make sense within your investment strategy. Selling solely for the tax benefit could leave you with a portfolio you wouldn’t otherwise choose. You’ll also need to be mindful of the wash-sale rule if you plan to purchase the same or a substantially identical investment around the time of the sale.

For investors with substantial taxable portfolios, it can help to review capital gains and losses across accounts before making individual trades.

2. Consider Donating Appreciated Investments

If charitable giving is already part of your plans, the asset you give can matter. Donating appreciated securities you’ve held for more than a year may allow you to claim a charitable deduction based on the investment’s fair market value, subject to applicable limits, while avoiding the capital gains tax you could have incurred by selling the investment first.

This can be particularly useful if you hold a highly appreciated or concentrated stock position and were already planning to make a charitable gift. The rules governing charitable deductions changed for 2026, making coordination with your tax professional particularly important when deciding what to give and when.

3. Evaluate Whether a Donor-Advised Fund Fits Your Giving Strategy

A donor-advised fund can allow you to make a charitable contribution now, potentially receive the corresponding deduction in the year of the contribution, and recommend grants to eligible charities over time.

For families who make significant charitable gifts, this can create more flexibility around the timing of the tax deduction. You might contribute several years of planned giving during a particularly high-income year or donate appreciated investments instead of cash.

Beginning in 2026, new limitations apply to charitable deductions for taxpayers who itemize. That makes it especially helpful to coordinate the timing and size of larger gifts with your CPA before year-end.

4. Review Your Required Minimum Distributions and QCD Opportunities

If you’re subject to required minimum distributions (RMDs), confirm that you’ve taken the appropriate amount from your retirement accounts before the applicable deadline.

If you’re at least age 70½ and regularly give to charity, a qualified charitable distribution (QCD) may also be a wise option. A QCD allows eligible IRA owners to transfer money directly from an IRA to a qualifying charity. The distribution may count toward an RMD while generally being excluded from taxable income, subject to IRS requirements and annual limits.

That distinction can be important because a QCD works differently from taking an IRA distribution and subsequently claiming a charitable deduction.

5. Maximize Tax-Advantaged Retirement Contributions

If you’re still working, review your retirement plan contributions before the year ends. For 2026, employees can contribute up to $24,500 to a 401(k), 403(b), or most 457 plans. The general catch-up contribution for participants age 50 and older is $8,000, bringing the potential total to $32,500. Participants ages 60 through 63 may qualify for the higher $11,250 catch-up contribution, for a total of $35,750.

The IRA contribution limit is $7,500 for 2026, plus a $1,100 catch-up contribution for those age 50 and older. Income and workplace-plan rules can affect whether a traditional IRA contribution is deductible and whether you’re eligible to contribute directly to a Roth IRA.

High earners should also be aware that beginning in 2026, certain catch-up contributions must be made on a Roth basis if prior-year wages from the plan sponsor exceeded the applicable $150,000 threshold.

6. Evaluate a Roth Conversion

A Roth conversion can be especially useful in a year when your taxable income is lower than usual or when you expect your tax rate to be higher in future years.

When you convert money from a traditional IRA to a Roth IRA, the taxable portion of the conversion is generally included in your income for that year. In exchange, qualified Roth IRA withdrawals can be tax-free, and Roth IRAs aren’t subject to lifetime RMDs for the original owner.

The decision requires more than comparing this year’s tax bracket with a future one. A conversion can affect Medicare premiums, taxation of other income, charitable planning, and the amount your heirs may eventually inherit in tax-deferred accounts. For high-income families, it often makes sense to model several conversion amounts before deciding how much to move.

7. Review Your HSA Contributions and Investment Strategy

If you’re eligible for a health savings account, an HSA offers several federal tax advantages. Contributions may be deductible or made pre-tax, investment growth within the account isn’t currently taxed, and qualified medical withdrawals can be tax-free.

For 2026, the contribution limit is $4,400 for self-only coverage and $8,750 for family coverage. People age 55 and older may generally contribute an additional $1,000.

If you have sufficient cash flow to pay current healthcare costs elsewhere, you may also choose to leave HSA assets invested for future qualified medical expenses. Keep your receipts and records if you’re using the account as part of a longer-term strategy.

8. Review Concentrated Stock and Equity Compensation

Executives and business owners can accumulate a significant amount of wealth in a single company. Year-end can be an organic time to review that exposure alongside your tax situation.

If restricted stock has vested, options have been exercised, or you’re considering selling company shares, look at the tax consequences before making the transaction. The timing of a sale can affect whether gains are taxed at short- or long-term capital gains rates, while exercising certain stock options can introduce additional tax considerations.

For someone with a concentrated position, charitable giving, tax-loss harvesting, and a planned diversification strategy may also intersect. These decisions are often better evaluated together than one transaction at a time.

9. Revisit Your Estate and Gifting Strategy

Year-end tax planning can extend beyond your annual income tax return.

For 2026, the federal annual gift tax exclusion is $19,000 per recipient. Married couples may potentially give $38,000 per recipient if the applicable requirements are met. The federal estate and gift tax basic exclusion amount is $15 million per individual in 2026.

Those thresholds don’t mean everyone should make large gifts. Giving assets away can have income tax, estate planning, cash flow, and family implications. For families with substantial estates, however, year-end is a natural time to review prior gifts, trusts, beneficiary designations, and future wealth-transfer plans with your estate attorney and tax advisor.

10. Coordinate With Your Financial and Tax Professionals Before December 31

Many tax decisions become more interconnected as wealth grows. Selling an appreciated investment could affect your charitable strategy. A Roth conversion could increase taxable income, while exercising stock options or realizing a large business gain could change which strategies make sense elsewhere.

This is why year-end planning is most impactful before the year has already ended. Your financial advisor can review your investments and broader financial plan, while your CPA can evaluate the tax consequences and your estate attorney can address legal and estate planning considerations.

Put Your Year-End Tax Strategies Into Action

The right year-end tax strategies will depend on your income, investment portfolio, charitable plans, retirement accounts, and estate. For affluent families, the value often comes from considering how those decisions interact before making changes in any one area.

At Comprehensive Advisor, we help clients evaluate investment and financial planning decisions alongside their broader goals and coordinate with their tax and legal professionals when appropriate.

If you’d like to review your financial plan before the end of the year, email us at [email protected] or call (760) 813-2125.

About Our Advisors

With nearly two decades of industry experience, Brett Gottlieb, and the team at Comprehensive Advisor provide personalized retirement planning and investment services. They help clients sift through the sea of investment options and make sense of what strategies are best suited for your unique needs. Our advisors customize financial strategies centered around “The Retirement Defense” process, a unique way we build your written plan that is designed to help get you to and through retirement by focusing on the key areas of your financial life. Our investment philosophy serves as a road map for helping you navigate the complexities of the financial landscape. By prioritizing capital preservation, emotional resilience, and personalized strategies, we help empower you to confidently pursue your financial goals and adapt to life’s changes.

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Neither the firm nor its agents or representatives may give tax or legal advice. Individuals should consult with a qualified professional for guidance before making any purchasing decisions. C.A. Financial & Insurance Services is not affiliated with the U.S. government or any governmental agency.

This article is meant to be general and is not investment or financial advice or a recommendation of any kind.

Please remember that converting an employer plan account to a Roth IRA is a taxable event. Increased taxable income from the Roth IRA conversion may have several consequences. Be sure to consult with a qualified tax advisor before making any decisions regarding your IRA. 4457528 – 9/26