Every December, someone sits down with our team and says some version of the same thing: “I wish we’d talked about this in October.” The holidays fill the calendar, the office closes for a week, and suddenly the deadlines that mattered most have come and gone.
Year-end planning doesn’t have to feel like a scramble. Most of the moves that make a real difference are simple on their own. The challenge is that they all share the same deadline, and they tend to affect one another in ways that aren’t obvious until you see them side by side.
That’s why we treat the last quarter of the year as a checkpoint. Below are ten moves worth reviewing now, while there’s still time to act thoughtfully instead of hurriedly.
1. Make the Most of Your Workplace Retirement Plan
For 2026, the IRS allows employees to defer up to $24,500 into a 401(k), 403(b), or most 457 plans. If you’re 50 or older, you can add an $8,000 catch-up contribution, and those between ages 60 and 63 may qualify for a larger “super catch-up” of $11,250. You can confirm current figures on the IRS contribution limits page.
Contributions generally have to come out of a paycheck by December 31, so now is the time to check your year-to-date total and adjust your deferral for the final few pay periods.
One new wrinkle for 2026: if you earned more than $150,000 in FICA wages last year, your catch-up contributions must now go in as Roth (after-tax) dollars. It’s worth confirming your plan is set up for this so your catch-up savings don’t stall.
2. Weigh a Roth Conversion While the Window Is Open
You have until the tax filing deadline to make an IRA contribution for the year, but Roth conversions follow a different clock. A conversion must be completed by December 31 to count toward this year’s taxes.
Converting part of a traditional IRA to a Roth means paying income tax now in exchange for tax-free withdrawals later. For many people in the years between retirement and Required Minimum Distributions, income is temporarily lower, which can make a measured conversion appealing. The right amount depends on your bracket, your Medicare premiums, and your long-term retirement planning goals, so this is one move best modeled before it’s made.
3. Take Your Required Minimum Distribution
If you’re 73 or older, your Required Minimum Distribution (RMD) from traditional IRAs and most workplace plans is generally due by December 31. Missing it can trigger a penalty of up to 25% of the amount you should have withdrawn.
There’s one exception for first-timers: your very first RMD can wait until April 1 of the following year. Delaying it, though, means taking two distributions in the same tax year, which can push you into a higher bracket. If you’ve inherited an IRA, annual distributions may apply to you as well. The IRS RMD FAQ page is a helpful starting point.
4. Give With a Plan, Not Just a Checkbook
Charitable giving is one of the most personal parts of any financial picture, and it also carries some of the most meaningful tax opportunities. Starting in 2026, the rules shifted. Taxpayers who take the standard deduction can now deduct up to $1,000 in cash gifts to qualifying charities ($2,000 for married couples filing jointly). Those who itemize will only deduct charitable gifts above 0.5% of their adjusted gross income.
If you’re 70½ or older, a Qualified Charitable Distribution (QCD) lets you send money directly from your IRA to a charity. The gift isn’t counted as taxable income, and it can satisfy all or part of your RMD. For larger or multi-year giving goals, a donor-advised fund may help you “bunch” several years of gifts into one. Our estate and charitable planning team can help you match the giving tool to your intentions.
5. Review Your Portfolio for Tax-Loss Harvesting and Rebalancing
Markets rarely move in a straight line, and by the fourth quarter most taxable portfolios hold a mix of gains and losses. Selling positions at a loss can offset realized gains and up to $3,000 of ordinary income, with any remainder carried forward to future years.
Be mindful of the wash-sale rule, which disallows the loss if you buy the same or a substantially identical investment within 30 days before or after the sale. Year-end is also a natural time to rebalance. If one part of your portfolio has grown well beyond its target, trimming it back helps keep your risk level aligned with your plan rather than with last year’s headlines. This is ongoing work within our investment management process, not just a December task.
6. Use Your FSA and Fund Your HSA
Flexible Spending Account dollars are often “use it or lose it.” Some employers allow a small carryover or a grace period into the new year, but many don’t. Check your balance and your plan’s rules, then schedule any eye exams, prescriptions, or appointments you’ve been putting off.
Health Savings Accounts work differently. Balances roll over indefinitely, and you have until the tax filing deadline to contribute for the year. For 2026, the limits are $4,400 for individual coverage and $8,750 for family coverage, plus a $1,000 catch-up if you’re 55 or older. Keep in mind that HSA contributions must stop once you enroll in Medicare.
7. Revisit Your Medicare Coverage During Open Enrollment
Medicare Open Enrollment runs from October 15 through December 7 each year. It’s the window to switch Medicare Advantage plans, change Part D prescription coverage, or move between Original Medicare and Medicare Advantage.
Plans change their premiums, drug lists, and provider networks every year, so the coverage that fit last year may not fit now. Reviewing your plan’s Annual Notice of Change and comparing options on Medicare.gov takes some time, but it can help you avoid surprise costs in January.
8. Make Annual Gifts and 529 Contributions
In 2026, you can give up to $19,000 per person to as many people as you’d like without filing a gift tax return. Married couples can give $38,000 per recipient together. Annual exclusion gifts don’t carry over, so if you planned to help children or grandchildren this year, the gift needs to be complete by December 31.
For families saving for education, a 529 plan can be a meaningful way to give. Alabama residents may deduct contributions to the state’s CollegeCounts 529 plan on their state return, up to $5,000 for single filers and $10,000 for joint filers. Contributions must be made by year-end to count.
9. Update Beneficiaries and Estate Documents
Beneficiary designations on retirement accounts, life insurance, and annuities override your will. If you’ve had a marriage, divorce, birth, or loss in your family, those forms may no longer reflect your wishes.
Year-end is a good moment to pull them out and confirm each one, along with your will, powers of attorney, and healthcare directives. With the federal estate tax exemption now set at $15 million per person, many families have more flexibility than they once did, but clear documents still matter just as much. A thoughtful legacy plan is one of the kindest things you can leave the people you love.
10. Check Your Withholding and Set the Stage for Next Year
If you had a large bonus, a property sale, or a Roth conversion this year, your tax withholding may have fallen behind. Increasing withholding on your final paychecks or making a fourth-quarter estimated payment (generally due January 15) can help you avoid an underpayment penalty.
Then look ahead. Review your emergency savings, any big expenses coming next year, and the goals that matter most to you. A few minutes of reflection in December can give you a clear starting point in January.
Why These Moves Work Best Together
Each item on this list is manageable on its own. The real value comes from seeing how they connect. A Roth conversion affects your tax bracket, which affects your Medicare premiums two years from now. A QCD can lower your taxable income while fulfilling your RMD. Harvesting a loss might make room for a larger conversion.
That interplay is exactly why our team approaches year-end through The Financial Peace of Mind Blueprint™. Instead of treating each deadline as a separate chore, we look at your full picture, model the options, and help you choose the combination that fits your goals. The goal is less guesswork and more confidence heading into the new year.
Frequently Asked Questions
What is the deadline for most year-end financial moves? December 31 is the cutoff for 401(k) deferrals, Roth conversions, RMDs, QCDs, annual gifts, and tax-loss harvesting. IRA and HSA contributions for the year can generally be made until the tax filing deadline the following spring.
Can a Qualified Charitable Distribution count toward my RMD? Yes. If you’re 70½ or older, a QCD sent directly from your IRA to an eligible charity can satisfy all or part of your RMD once you reach RMD age, and the amount is excluded from your taxable income.
Is October too early to start year-end planning? Not at all. Starting in the fall gives you time to gather numbers, compare options, and act without rushing. Some steps, like Medicare Open Enrollment, close in early December.
Let’s Finish the Year Well
You’ve worked hard all year, and the decisions you make in these final weeks can help that effort go further. If you’d like a second set of eyes on your year-end checklist, or simply want to understand how these pieces fit your situation, our team would be glad to walk through it with you.
This article is for educational purposes and does not constitute investment, tax, or legal advice. Investing involves risk, markets fluctuate, and outcomes are never guaranteed. Strategies should be tailored to your individual goals, timeline, and risk tolerance. Contribution limits, thresholds, and deadlines are subject to change. Please consult a qualified financial, tax, or legal professional before making decisions based on this information.
