7 Year-End Tax Moves to Help You Save Thousands

By George P. Jackson, MBA, CPA, CFA, CFP®, CMT, CLU, ChFC

Actionable strategies for affluent investors to trim their 2025 tax bill, including Roth conversions, gain harvesting, and giving strategies.

As the end of 2025 approaches, affluent investors have a prime opportunity to implement strategic tax moves that can significantly reduce their tax liability. By acting before December 31, you can leverage deductions, optimize investments, and position yourself for long-term financial success. 

Here are seven year-end tax strategies to consider, designed to help you keep more of your wealth.

1. Maximize Roth Conversions for Future Tax-Free Growth

Converting a traditional IRA or 401(k) to a Roth IRA can be a powerful way to manage your future tax burden. While you’ll pay taxes on the converted amount now, Roth IRAs grow tax-free, and qualified withdrawals in retirement are also tax-free. This is especially valuable if you expect to be in a higher tax bracket later or if tax rates rise.

Why it works: With potential tax law changes on the horizon, locking in today’s tax rates could save you significantly. For 2025, evaluate your taxable income and convert an amount that keeps you within your current tax bracket.

Action step: Work with a financial advisor to calculate the optimal conversion amount. For example, if you’re in the 24% tax bracket (up to $394,600 for married couples filing jointly in 2025), convert just enough to stay below the next bracket threshold. Spread conversions over multiple years to manage the tax hit.

2. Harvest Capital Gains Strategically

Tax-loss harvesting gets a lot of attention, but tax-gain harvesting can be just as effective for affluent investors. If you’re in a lower tax bracket this year (e.g., 0% or 15% for long-term capital gains), consider selling appreciated assets to lock in gains at a low or zero tax rate.

Why it works: For 2025, the 0% long-term capital gains rate applies to taxable income up to $48,350 for single filers and $96,700 for married couples filing jointly. By realizing gains now, you can reset your cost basis and reduce future tax liability when you sell again.

Action step: Review your investment portfolio for appreciated stocks or funds. Sell enough to utilize the 0% or 15% capital gains bracket, then reinvest the proceeds to maintain your portfolio’s allocation.

3. Accelerate Charitable Giving With a Donor-Advised Fund

Charitable giving is a win-win: you support causes you care about while reducing your taxable income. For affluent investors, a donor-advised fund (DAF) is an efficient way to bundle charitable contributions. By contributing appreciated securities or cash to a DAF, you can claim an immediate tax deduction while distributing funds to charities over time.

Why it works: Donating appreciated assets avoids capital gains taxes, and you can deduct up to 60% of your adjusted gross income (AGI) for cash donations or 30% for appreciated securities in 2025.

Action step: Identify low-basis stocks or other assets in your portfolio. Contribute them to a DAF before year-end to maximize your deduction. If you don’t have a DAF, set one up through a reputable provider like Fidelity or Schwab Charitable.

4. Max Out Retirement Contributions

Contributing the maximum to your retirement accounts not only boosts your nest egg but also reduces your taxable income. For 2025, the contribution limits are:

• 401(k), 403(b), or 457 plans: $23,500 (plus $7,500 catch-up for those 50+)
• Traditional IRA: $7,000 (plus $1,000 catch-up for those 50+)
• SEP-IRA or solo 401(k) (for self-employed): Up to $70,000 or 25% of net self-employment income, whichever is less

Why it works: Contributions to traditional plans are tax-deductible, lowering your 2025 tax bill. If you’re self-employed, a SEP-IRA or solo 401(k) offers higher limits to defer significant income.

Action step: Review your contributions to date and increase them before year-end. If you’re self-employed, consult a tax professional to determine the maximum allowable contribution based on your income.

5. Take Advantage of Tax-Loss Harvesting

Tax-loss harvesting involves selling investments at a loss to offset capital gains and up to $3,000 of ordinary income annually. Any excess losses can be carried forward to future years.

Why it works: By offsetting gains with losses, you reduce your taxable income. This is particularly useful if you’ve realized significant gains earlier in the year or through gain harvesting.

Action step: Review your portfolio for underperforming assets. Sell them before year-end, but be mindful of the wash-sale rule: don’t repurchase the same or a “substantially identical” security within 30 days. Consider reinvesting in a similar but distinct asset, like swapping one ETF for another in a different index.

6. Optimize Your Giving With a Qualified Charitable Distribution

If you’re of RMD age (70½ or older in 2025), you can make a qualified charitable distribution (QCD) from your IRA, directly transferring up to $108,000 in 2025 (indexed for inflation) to a qualified charity. This counts toward your required minimum distribution (RMD) but isn’t included in your taxable income.

Why it works: QCDs lower your AGI, which can reduce taxes on Social Security benefits, Medicare premiums, and other income-based calculations. Unlike regular deductions, QCDs don’t require itemizing.

Action step: If you’re subject to RMDs, instruct your IRA custodian to make a QCD to your chosen charity before December 31. Ensure the transfer goes directly to the charity to qualify.

7. Prepay Deductible Expenses

If you expect to itemize deductions in 2025, consider prepaying certain expenses before year-end to boost your deductions. These could include property taxes, state income taxes (up to the $40,000 SALT cap subject to income limits), or medical expenses (deductible if they exceed 7.5% of AGI).

Why it works: Bunching deductible expenses into one year can push you over the standard deduction ($15,750 for single filers, $31,500 for married couples filing jointly in 2025), maximizing your tax savings.

Action step: Review your itemized deductions to date. If you’re close to the standard deduction threshold, prepay property taxes or schedule elective medical procedures before year-end. Alternatively, if 2026 will be a higher-income year, consider deferring expenses to maximize deductions then.

We Can Help You Make Your 2025 Tax Moves Count

The end of 2025 is a critical window to implement these tax-saving strategies. However, tax planning is highly personal, and the best moves depend on your income, portfolio, and financial goals. Consult with a CPA or financial advisor to tailor these strategies to your situation. By acting now, you can trim your 2025 tax bill and set yourself up for a more tax-efficient future.

The Jackson Wealth Management, LLC team is here to help. Ready to take control of your financial future? Schedule a consultation today or calling (407) 585-0235, emailing gj@jacksonwm.com, or booking online.

About George

George P. Jackson is the CEO and CIO of Jackson Wealth Management, LLC, based in Lake Mary, Florida. With over 33 years of experience in the financial services industry, George is passionate about making a meaningful difference in his clients’ lives through comprehensive, integrated wealth management. He specializes in helping clients make confident financial decisions by serving as their trusted “one-stop shop” for anything money related, from investments and retirement planning to taxes and estate strategies.

George obtained his Bachelor of Business Administration as well as his Master of Business Administration (with an emphasis in quantitative analysis) from University of Cincinnati. His designations include Certified Public Accountant (CPA), Chartered Financial Analyst®, CERTIFIED FINANCIAL PLANNER®, Chartered Market Technician®, Chartered Life Underwriter®, and Chartered Financial Consultant®. Outside the office, he enjoys tennis, flying airplanes, traveling, spending time with his adult children, Christina and Matthew, and anything to do with the ocean. To learn more about George, connect with him on LinkedIn.

Disclaimer: This blog post is for informational purposes only and does not constitute tax or financial advice. Always consult a qualified professional before making financial decisions. Tax laws and limits are based on 2025 projections and may be subject to change. Always verify with a tax professional for the most current information.