A Retiree’s Guide to Key Dates in 2021

It's critical -- and financially sound -- to hit these important financial deadlines spaced throughout the year.

Retiree at table with open laptop looking at a calendar
(Image credit: Getty Images )

Planning is everything. financial strategies can take years to put in motion and even longer to bear fruit. The last thing you want is to sabotage yourself by missing an important financial deadline, like any one of these dates in 2021. Use this guide as a checklist and reminder of what you will need to do.

Jan. 1 A new year is your cue to take stock of your retirement savings. Employees over 50 can contribute up to $26,000 ($19,500 for younger workers) to an employer’s saving plan in 2021, the same amount as last year. Also unchanged are the annual maximums that you can squirrel away in a traditional or Roth IRA: $7,000 for those age 50 and older ($6,000 for everyone else). You’ll need earned income to contribute to an IRA, and the contribution amounts cannot exceed your earnings, though the age limit is gone. Beginning in 2020, people 70½ and older who are still employed can continue socking away money into an IRA.

Medicare’s general enrollment period, which runs until March 31, begins today, with coverage starting July 1. During this period, those who missed signing up for Medicare at age 65 and don’t qualify for a “special enrollment period” can enroll in parts A and B, and Medicare Advantage beneficiaries can switch to a different Advantage plan or to traditional Medicare.

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Jan. 15 Fourth quarter estimated taxes are due, or skip this deadline by filing your 2020 taxes and paying the remaining balance by Jan. 31.

Mar. 31 General enrollment for traditional Medicare and open enrollment for Medicare Advantage end.

Apr. 1 The waiver of 2020 required minimum distributions makes this April 1 deadline for taking the first RMD moot. Plus, if you turned 70 on July 1, 2019, or later, you now have until age 72, not 70½, to start taking withdrawals from tax-deferred retirement saving accounts, with a deadline of April 1, 2022, for the first RMD.

Apr. 15 Your 2020 federal taxes are due, along with any money owed, even if you file for a six-month extension. This is also your last chance to make 2020 contributions to an IRA. Plus, your first estimated tax payment for 2021 is due.

June 15 Second quarter estimated taxes are due.

July 1 Avoid penalties for any underpayment of 2021 estimated taxes with a midyear review. One way to dodge the penalties: Pay at least 90% of the current-year tax tab or 100% of the prior-year tax tab (110% if you have a high income). Consider other moves to trim your 2021 tax bill.

Sept. 15 Your third estimated tax payment for 2021 is due. If you’ve fallen behind on payments or just want a simpler way to pay, withholding the tax from your RMD at any point in 2021—even the last day of December—is treated as if you had paid federal taxes steadily throughout the year.

Sept. 30 By this date, you should have Medicare’s annual notice of changes to formularies, benefits and premiums for either a Medicare Advantage or Part D prescription drug plan. Changes take effect in 2022.

Oct. 15 For all you extension filers, this is the deadline to turn in your 2020 tax return. Also, Medicare open enrollment begins today. You have from now to Dec. 7 to switch between traditional Medicare and Medicare Advantage, or choose new Advantage and Part D plans, with coverage effective in 2022.

Nov. 1 Starting today, early retirees in most states have until Dec. 15 to buy health insurance for 2022 on the Affordable Care Act’s exchanges.

Dec. 1 If you plan to make a qualified charitable distribution from your IRA, act now to ensure that the charity receives the money in time. Traditional IRA owners 70½ or older can transfer up to $100,000 directly to charity in 2021 with a QCD.

Dec. 7 Medicare’s open enrollment ends.

Dec. 15 The ACA’s open enrollment ends. If you haven’t already done so, take your 2021 RMD now.

Dec. 31 By year-end, your RMD must be out of your IRA and any QCDs should be in the charity’s account.

Managing Editor, Kiplinger's Retirement Report

Siskos is an old hat with the Kiplinger brand. More than a decade ago, she spent eight years writing about personal finance for Kiplinger's Personal Finance magazine, including a monthly column—Starting Out—that served young adults. That was in her salad days. Now she's turned her attention to an audience she hopes to join in a decade or so: retirees. Siskos is the managing editor for Kiplinger's Retirement Report. In between, she broadened her personal-finance repertoire with real estate and investing stories at Old-House Journal, Investing Daily and U.S. News. She comes to Kiplinger by way of the Newseum, where she worked as an exhibit editor.