Annual Retiree To-Dos: RMDs, Medicare, Social Security & More

Retirement doesn’t mean your financial responsibilities stop. In many ways, they become more complex. From managing taxes to securing healthcare and making strategic decisions about your investments and legacy, the post-retirement years require annual check-ins to ensure your long-term plan remains aligned with your evolving financial goals.

Whether you are recently retired or well into your retirement journey, this comprehensive checklist will help you stay proactive and confident in your financial future.

1. Take Required Minimum Distributions (RMDs)

When:

• For those born in 1959 or earlier: starting at age 73
• For those born in 1960 or later: age 75

Deadline: December 31st each year. For your first RMD, you can delay until April 1st of the following year – but doing so means taking two RMDs in one tax year, potentially increasing your tax bill.

Key Reminders:

• RMDs apply to traditional IRAs, 401(k)s, 403(b)s, and similar accounts.
• Does not apply to Roth IRAs (unless inherited).
• The amount is based on your account balance on December 31 of the previous year and your respective IRS life expectancy table.
• Failure to take your RMD can result in a 25% penalty on the amount not withdrawn

Best Practice: Work with your financial advisor to strategically time and optimize withdrawals across accounts. This can help minimize taxes, maintain cash flow, and preserve your long-term wealth.

2. Enroll in or Evaluate Your Medicare Plan

Initial Enrollment: Starts 3 months before you turn 65 and lasts for 7 months (includes your birth month + 3 months after).

Annual Open Enrollment: October 15th – December 7th (plan changes take effect January 1st).

Medicare Advantage Open Enrollment: January 1st – March 31st.

Key Areas to Review Annually:

• Prescription drug coverage (Part D) formulary changes.
• Medicare Advantage vs. Original Medicare comparison.
• Supplemental (Medigap) coverage for those who want more predictable out-of-pocket expenses.

Best Practice: Reevaluate your healthcare needs and provider networks each year. Even if your coverage seemed perfect last year, plan changes can affect costs and care.

3. Plan Your Social Security Strategy

Eligibility: Take as early as 62, at full retirement age between 66–67 or delayed up to age 70.

Impact:

• Claiming before full retirement age results in a permanent reduction in your monthly benefit. Delaying after full retirement age increases your benefit by up to 8% per year until age 70.

Best Practice: Developing a coordinated plan with your financial advisor can help maximize your benefits – especially for married couples or widows/widowers – and optimize tax outcomes if you’re drawing from other retirement accounts.

4. Review Your Tax Plan

Retirement doesn’t exempt you from tax obligations – especially with multiple income streams from RMDs, Social Security, pensions, or investments.

To-Do:

• Make quarterly estimated tax payments if your income isn’t subject to withholding.
• Consider Roth conversions during lower-than-average income years.
• Consider charitable giving strategies like Qualified Charitable Distributions (QCDs, starting at age 70½), to reduce taxable income.

Best Practice: Tax efficiency is one of the clearest ways to preserve wealth. Coordinate with your tax advisor and financial advisor to project income and smooth your tax liabilities throughout retirement.

5. Update Estate Plan & Beneficiaries

A lot can change in a year – family dynamics, asset values, and tax laws. Your estate plan should reflect your current wishes and take advantage of planning opportunities.

To-Do:

• Review wills, trusts, healthcare directives, and powers of attorney.
• Update beneficiary designations on retirement accounts, life insurance policies, and transfer-on-death (TOD) accounts.
• Reassess charitable giving and legacy strategies to align with your values and goals

Best Practice: Meet annually with your estate attorney and financial advisor to ensure your plan reflects your wishes and is structured to minimize estate taxes and probate issues.

→ Learn the four most common times you need to review your estate plan.

6. Review Insurance & Long-Term Care Policies

Insurance needs evolve as you age, but they don’t disappear. Everyone can benefit from the right coverage.

To-Do:

• Review long-term care insurance options or explore alternatives, like hybrid policies or the ability to self-fund.
• Evaluate life insurance for purposes like estate liquidity, tax-efficient inheritance, or charitable giving.
• Confirm you have adequate liability coverage, especially if you own property or have household staff.

Best Practice: Insurance should serve a specific role in your plan; not just be a product you continue to carry “just in case.” Reassess your need each year.

→ Learn how to determine how much life insurance you really need.

7. Review Investment Allocation & Spending Strategy

Your risk tolerance, cash needs, and investment goals naturally evolve over time.

To-Do:

• Evaluate your withdrawal strategy to ensure it aligns with your spending plan and tax considerations.
• Review risk tolerance and asset allocation to match current goals and market conditions.
• Reassess asset location to ensure investments are held tax-efficiently (e.g., placing income-generating assets in tax-deferred accounts and growth assets in taxable or Roth accounts).

Best Practice: Avoid making drastic moves based on market headlines. A disciplined, long-term strategy is especially important in retirement and is key to maintaining peace of mind.

An Annual Review of Your Plan Is Not Optional

Each item in this checklist plays a vital role in a well-managed retirement – and missing even one can lead to unnecessary costs or complications. Working with a financial advisor ensures these pieces stay coordinated and you remain financially secure throughout retirement.

As your life evolves, your retirement plan should evolve, too. Make an annual financial review part of your retirement routine – it’s one of the most valuable habits you can form in this next chapter.

Please consult with an attorney or a tax or financial advisor regarding your specific legal, tax, estate planning, or financial situation. The information in this article is not intended as legal or tax advice.