Your Yearly Retirement Check-Up

The story: Walt’s money calendar

Walt pins a yearly calendar to the wall with a few money tasks for each season, and Ruth adds the year-end deadlines.

1. Walt: Last year I missed Medicare Open Enrollment and paid more for my drug plan than I had to.
2. Ruth: I keep a money calendar. A few tasks each season, at the same times every year.
3. Narrator: Around the new year, benefit and premium letters arrive, and taxes follow. Fall brings Medicare Open Enrollment.
4. Narrator: By December 31: required withdrawals, gifts to charity from an IRA and any Roth conversions.
5. Ruth: And once a year, I re-run my plan and compare it with last year’s.
6. Walt: Same times, every year. I can do that.

What you’ll learn

1. Winter: letters, then taxes

   Around the new year, Social Security’s cost-of-living (COLA) letter and Medicare premium letters arrive. Taxes follow. If you pay estimated tax, the usual due dates are April 15, June 15, September 15 and January 15.

2. Fall: Medicare Open Enrollment

   Each fall, Medicare Open Enrollment lets you compare and switch health and drug plans. Plans and costs change every year, so a quick check can save real money. Dates are on Medicare.gov.

3. By December 31

   Most required withdrawals (RMDs), gifts to charity straight from an IRA (QCDs), Roth conversions and choices about selling at a gain or loss count for the calendar year. Finish them by December 31.

4. Any time, once a year

   Check beneficiaries, documents, trusted contacts and credit freezes. If income dropped for a qualifying reason, ask Social Security to use the newer income for Medicare. Then re-run your plan and compare it with last year’s.

Key words

annual review

your yearly money check-up

year-end deadline

a December 31 cutoff

qualified charitable distribution

a gift to charity straight from an IRA

Also called: QCD

Common questions

Can I get reminders for these dates?

Many people put them on a paper or phone calendar, with a reminder a few weeks before each one.

What if I miss a deadline?

Most can be fixed. Act as soon as you notice, and ask the agency or a tax pro how to correct it. Fixing quickly usually lowers any penalty.

Remember this

Fall: Medicare. Winter: taxes. December: RMDs, gifts and conversions.

Try it: Start your yearly check-up

1. Pick the same date each year for your check-up.
2. Run the public retirement calculator and save or print the result with today’s date.
3. Next year, compare the new result with this one.

No account: use the public Retirement Calculator (/tools/retirement-calculator).

Live facts

Numbers that change over time, with when they were last checked and where they come from.

• Estimated tax due dates

  April 15, June 15, September 15 and January 15

  When people with income that has no withholding usually pay quarterly tax (dates move to the next business day on weekends and holidays)

  As of February 8, 2026

  Source: IRS.gov(opens in a new tab)

• Medicare Part B standard premium

  $202.90a month

  What most people pay each month for Part B; higher incomes pay more

  As of 2026

  Source: Medicare.gov(opens in a new tab)

• This year’s Social Security cost-of-living adjustment (COLA)

  Source: SSA.gov(opens in a new tab)

• Medicare Open Enrollment dates

  Source: Medicare.gov(opens in a new tab)