2025 Year-End Financial Checklist for Retirees

As the year wraps up, many retirees use this season as a chance to get organized, prepare for the new year, and make sure their financial plan is running smoothly. A few small steps in December can help you start January with more clarity — especially when it comes to taxes, required withdrawals, charitable giving, and investment planning.

Below is a simple year-end checklist designed to help you think through the most important areas of your financial life. Not every item will apply to everyone, but reviewing these categories can help you make intentional decisions before the calendar turns.

1. Review Your Required Minimum Distributions (RMDs)

If you’re age 73 or older (based on current IRS rules), make sure any required distributions from IRAs or employer retirement plans are completed before December 31.

Missing an RMD deadline can result in significant penalties, so it’s helpful to confirm:

• All accounts requiring an RMD have been satisfied
• Beneficiary IRA rules are being followed correctly
• Any Qualified Charitable Distributions (QCDs) have been properly processed

If you’re not yet taking RMDs but will soon, it may be worth estimating future withdrawals to understand how they’ll affect your taxes.

2. Consider a Qualified Charitable Distribution (QCD)

If you’re 70½ or older, a QCD allows you to send up to $100,000 from an IRA directly to a qualified charity.
A QCD:

• Can satisfy part or all of your RMD
• Keeps the distribution out of taxable income
• Can be a helpful strategy if you no longer itemize deductions

For retirees who already give charitably, this can be one of the most tax-efficient year-end moves available.

3. Review Your Tax Withholding and Estimated Payments

Year-end is a good time to check whether your current withholdings (from Social Security, pensions, or IRA withdrawals) align with your expected tax liability.
This can help you avoid:

• Underpayment penalties
• A large tax bill in April
• Withholding too much throughout the year

A quick check-in can help you enter the new year with the right settings.

4. Evaluate Roth Conversions (If Appropriate)

The last weeks of the year are often when retirees consider partial Roth conversions, especially if:

• Your income is lower than usual
• You have room left in your current tax bracket
• You want to reduce the size of future RMDs
• You’re planning for longer-term tax flexibility

Roth conversions aren’t right for everyone, but they can be worth evaluating before December 31, since conversions must be completed by year-end to count for the current tax year.

5. Review Investment Performance and Rebalance If Needed

Now is a good time to check whether your investment allocation still aligns with your retirement plan. Markets shift throughout the year, and that can change your level of risk exposure.

A year-end review can help you:

• Rebalance back to your target allocation
• Revisit cash reserves for next year’s income
• Evaluate whether any realized gains fit your broader plan

The goal isn’t to chase performance — it’s simply to stay inline with a thoughtful long-term strategy.

6. Check Beneficiaries and Estate Documents

Even small changes in your life or family can affect your estate plan. Year-end is an ideal time to confirm that:

• Beneficiary designations on retirement accounts and life insurance are accurate
• Powers of attorney and healthcare directives reflect your current wishes
• Your trust or will is still consistent with your goals
• Any major life updates (new grandchildren, losses, moves, etc.) are accounted     for

Keeping this paperwork current can prevent future complications for your loved ones.

7. Review Healthcare and Medicare Elections

Open enrollment periods often fall toward the end of the year, which makes this a good time to revisit:

• Medicare Advantage vs. Medigap plans
• Prescription drug coverage
• Out-of-pocket maximums
• Anticipated healthcare needs in the coming year

Even if nothing changes, confirming the details can help avoid surprises.

8. Revisit Your Spending Plan for the Upcoming Year

Retirement spending isn’t static — it changes as life changes. Reviewing the past year can help you understand what worked well and what needs adjustment.
This might include:

• Travel and family plans
• Housing costs
• Charitable goals
• Large one-time expenses
• Income sources you expect to shift

A quick review can help ensure your financial plan continues to support your priorities.

Bringing It All Together

Year-end planning doesn’t have to be complicated. A simple, consistent review each December can help you stay organized, reduce surprises, and make intentional choices about the year ahead.

If you’d like help reviewing your finances before January or want to understand how these decisions fit into your broader retirement plan, I’m always glad to talk through what that process can look like.

A little preparation now can set the stage for a more confident start to the new year.‍

You can schedule a short Discovery Call with Stillwater Financial Planning if you’d like help aligning your financial decisions with your long-term goals.

This is not an offer to buy or sell securities. No investment process is free of risk and there is no guarantee that the investment process described herein will be profitable. Investors may lose all of their investments. Past performance is not indicative of current or future performance and is not a guarantee.

Investment advice offered through IHT Wealth Management, a registered investment advisor.