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Getting ready for Medicare? Here’s your pre-enrollment checklist

By Bonnie Vengrow

For many people, turning 65 means it’s time to sign up for Medicare. But experts say you should start preparing for enrollment long before then — ideally, about a year or so before your big day.

That’s because Medicare is different from other health insurance you’ve had in the past. There’s an alphabet soup of parts to learn, enrollment windows to remember, late enrollment penalties to avoid and a wide array of coverage options to explore.

The month-by-month Medicare checklist below helps take the guesswork out of preparing for your enrollment.

12 months before your 65th birthday

At this point, you should have a general idea of what your retirement plan will be. And chances are, it will involve Medicare. “Now is the time to start educating yourself on the basics of the program,” says Ed Bennett, lead director of sales for Aetna Medicare Transition Services.

This includes learning the various parts of Medicare and what each part covers: Part A (hospital insurance), Part B (medical insurance), Part D (prescription drugs), Part C (Part A & B coverage plus extra benefits) and Medical Supplement Insurance (Medigap).

If you plan on working past the age of 65, you also need to coordinate your workplace coverage with Medicare. Certain circumstances, such as the size of your company, can impact when you need to enroll.

9 months before your 65th birthday

Now that you’re familiar with the coverage options, you’re ready to examine the costs associated with Medicare. As you’ll come to learn, these often depend on your individual circumstances.

The first question you’ll want to answer is whether you qualify for premium-free Part A. If you or your spouse worked and paid Medicare taxes for 10 years or more, you will qualify. Most people do. If you decide to enroll in Part B, you will pay a monthly premium regardless of your work history.

You’ll also want to find out all of the other costs associated with each part of Medicare. This includes monthly premiums, copays, coinsurance and deductibles. Medicare.gov has a breakdown of the costs.

Keep in mind that your income could impact how much you pay for certain parts of Medicare. High earners, for example, pay an extra charge, called an Income-Related Monthly Adjustment Amount (IRMAA), in addition to their monthly premiums for Part B and Part D. (In 2023, that included individuals who earned $97,000 or more or couples who earned $194,000 or more.) If your income falls below a certain amount, you may qualify for financial assistance with Medicare.

6-9 months before your 65th birthday

Determine when it makes sense for you to transition from your existing coverage to Medicare. If you’re planning to continue working after your 65th birthday and delay signing up for certain parts of Medicare, Bennett recommends having a target retirement date in mind. You’ll want to time your enrollment around that date to avoid penalties and gaps in coverage.

4-6 months before your 65th birthday

Bennett recommends meeting with a Medicare agent, who can help you fine-tune your choices. This may include determining whether Original Medicare or Medicare Advantage is right for you and whether you need Part D or Medicare Supplement Insurance.

During this time, you should also check that the doctors, hospitals and pharmacies you like accept Medicare or are part of the Medicare Advantage network you’re considering.

1-3 months before your 65th birthday

Your Initial Enrollment Period (IEP) is underway. This is the seven-month window when you can enroll in Medicare. It runs from three months before the month you turn 65, through your birthday month to three months after the month you turn 65. If your birthday is on the first of the month, your IEP begins four months before you turn 65 and ends 2 months after the month you turn 65.

Set a date on your calendar to enroll and be sure it’s within the seven-month window. Otherwise, you could incur late enrollment penalties.

In addition to your enrollment window, be mindful of when your coverage will begin. The start date depends on when you sign up. For example, if you enroll during the first three months of your IEP, coverage begins the first day of the month you turn 65. But if you enroll the month you turn 65, then your coverage begins one month after you sign up.

Once you’re enrolled in Medicare, you can decide whether to enroll in a Medicare Advantage plan, a Part D plan or Medicare Supplement Insurance.

Look for your red, white and blue Medicare card in the mail. If you have a Medicare Advantage or Part D plan, you’ll receive a separate ID card. Your Evidence of Coverage (EOC), which details what benefits are covered and what your costs will be, will be posted online. You will receive a link to it by email. You can also request to have a printed copy mailed to you.

With your coverage finalized, you’ll want to set up a “Welcome to Medicare” visit with your doctor. This one-time checkup is available at no extra cost within the first 12 months of signing up for Medicare and serves as a baseline for your annual wellness checkups.  

Your Medicare to-do list infographic

Your Medicare to-do list

 

Starting to think about Medicare? Use this to-do list to help you prepare for enrollment.

 

12 months before your 65th birthday

Determine if you qualify for Medicare coverage.

Explore the different parts of Medicare.

Research how your current coverage works with Medicare.

 

9 months before your 65th birthday

Research Medicare costs.

Find out whether you qualify for premium-free Part A.

Learn about financial assistance options. Apply if you think you might qualify.

 

6-9 months before your 65th birthday

Determine the right time for you to enroll.

Working past 65 and delaying enrolling? Set your retirement date and time your sign-up around then to avoid penalties.

 

4-6 months before your 65th birthday

Consider meeting with a licensed Medicare agent to help you navigate the enrollment process.

Determine whether Original Medicare (Parts A and B) or a Medicare Advantage plan is right for you.

Check if your doctors accept Medicare or Medicare Advantage.

Research Medicare Advantage plans. (The Aetna Medicare plan finder tool can help.)

Figure out if you need a Part D plan or Medicare Supplement Insurance.

 

1-3 months before your 65th birthday

Enroll during your Initial Enrollment Period.

Be mindful of when your coverage begins.

Once you’re enrolled, decide whether to enroll in Medicare Advantage, Part D or Medicare Supplement Insurance.

Look for your Medicare card — it usually arrives within 30 days of being approved.

Set up a “Welcome to Medicare” visit with your doctor.

Start exploring how to make the most of your Medicare.

Your Medicare to-do list infographic

Your Medicare to-do list

 

Starting to think about Medicare? Use this to-do list to help you prepare for enrollment.

 

12 months before your 65th birthday

Determine if you qualify for Medicare coverage.

Explore the different parts of Medicare.

Research how your current coverage works with Medicare.

 

9 months before your 65th birthday

Research Medicare costs.

Find out whether you qualify for premium-free Part A.

Learn about financial assistance options. Apply if you think you might qualify.

 

6-9 months before your 65th birthday

Determine the right time for you to enroll.

Working past 65 and delaying enrolling? Set your retirement date and time your sign-up around then to avoid penalties.

 

4-6 months before your 65th birthday

Consider meeting with a licensed Medicare agent to help you navigate the enrollment process.

Determine whether Original Medicare (Parts A and B) or a Medicare Advantage plan is right for you.

Check if your doctors accept Medicare or Medicare Advantage.

Research Medicare Advantage plans. (The Aetna Medicare plan finder tool can help.)

Figure out if you need a Part D plan or Medicare Supplement Insurance.

 

1-3 months before your 65th birthday

Enroll during your Initial Enrollment Period.

Be mindful of when your coverage begins.

Once you’re enrolled, decide whether to enroll in Medicare Advantage, Part D or Medicare Supplement Insurance.

Look for your Medicare card — it usually arrives within 30 days of being approved.

Set up a “Welcome to Medicare” visit with your doctor.

Start exploring how to make the most of your Medicare.

Download checklist

By giving yourself plenty of time to prepare for Medicare enrollment, you can choose the coverage that’s right for you and learn how make the most of your benefits.

©2023 Aetna Inc.

About the author

Bonnie Vengrow is a journalist based in NYC who has written for Parents, Prevention, Rodale’s Organic Life, Good Housekeeping and others. She’s never met a hiking trail she doesn’t like and is currently working on perfecting her headstand in yoga class.

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