Medicare Checklist: What to Do Before You Turn 65

If you’re approaching your 65th birthday, congratulations—you’re about to unlock one of the most important benefits in the U.S. healthcare system: Medicare. But along with the relief of knowing you’ll have coverage comes a flood of questions. What do you need to do? When should you start? Which parts of Medicare do you actually need?

The good news is that getting ready doesn’t have to be stressful. With a clear Medicare checklist, you can take each step in order, prepare early, and transition smoothly into coverage that fits your life.

This guide is designed to walk you through everything you need to know before you turn 65, from understanding enrollment periods to making decisions about supplemental coverage. Think of it as your personal roadmap.

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Why a Medicare Checklist Matters

Medicare isn’t one-size-fits-all. What’s right for your neighbor may not be right for you. Preparing early helps you avoid:

• Late enrollment penalties (which can last for life).
• Coverage gaps where you’re uninsured.
• Overpaying for plans you don’t need.
• Losing access to your doctors or prescriptions.

Planning ahead also gives you peace of mind. Instead of scrambling at the last minute, you’ll feel confident knowing exactly what’s coming and how to handle it.

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Step 1: Understand the Basics of Medicare

What Medicare Covers

Medicare is made up of different “parts,” and understanding them is the first step in your Medicare checklist:

• Part A (Hospital Insurance): Covers inpatient hospital stays, skilled nursing, hospice, and some home health care.
• Part B (Medical Insurance): Covers outpatient services like doctor visits, preventive care, lab tests, durable medical equipment, and some home health.
• Part C (Medicare Advantage): Private insurance plans approved by Medicare that bundle Parts A and B (and often Part D). They may also include extras like vision, dental, or fitness benefits.
• Part D (Prescription Drug Coverage): Helps pay for prescription medications.

Medicare Isn’t Free

Part A is usually premium-free if you or your spouse paid Medicare taxes for at least 10 years. Part B, C, and D have monthly premiums, deductibles, and out-of-pocket costs.

Knowing these basics makes the rest of your Medicare checklist easier.

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Step 2: Mark Your Enrollment Window

When You Can Enroll

Your Initial Enrollment Period (IEP) is a 7-month window:

• Starts 3 months before your 65th birthday month.
• Includes your birthday month.
• Ends 3 months after your birthday month.

Example: If you turn 65 in July, your IEP runs from April through October.

Why Timing Matters

• If you sign up early, your coverage starts on time.
• If you miss it, you may pay penalties—sometimes permanently.
• If you’re still working and have employer coverage, your timeline may be different (more on that in Step 4).

Add this to your Medicare checklist: write your enrollment window on your calendar.

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Step 3: Decide If You Need to Enroll Right Away

Not everyone has to enroll in Medicare at 65.

• If you’re retired or don’t have employer coverage: You need to sign up during your Initial Enrollment Period.
• If you have employer coverage through your job or your spouse’s job: You may be able to delay Part B without penalty.
• If you’re on COBRA or retiree coverage: These don’t count the same way—Medicare rules can be tricky. Always check with your HR or benefits office.

Part of your Medicare checklist should be asking: “Do I need to enroll now, or can I wait?”

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Step 4: Compare Original Medicare vs. Medicare Advantage

This is where your choices really start.

Original Medicare

• Includes Part A and Part B.
• Lets you see any doctor or hospital that accepts Medicare (broad access).
• Doesn’t include prescription coverage—you’ll need a Part D plan.
• Leaves gaps in coverage—deductibles and 20% coinsurance for most services.

Medicare Advantage (Part C)

• Bundles Part A, Part B, and usually Part D.
• May include extras like dental, vision, hearing, and fitness.
• Has set provider networks (HMO or PPO).
• Often lower upfront premiums but more cost-sharing when you use care.

Add to your Medicare checklist: Do I prefer broad access (Original Medicare + Medigap) or bundled convenience (Medicare Advantage)?

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Step 5: Don’t Forget Prescription Coverage

Even if you don’t take many prescriptions now, you’ll want to enroll in Part D or a Medicare Advantage plan that includes drug coverage. Skipping this step leads to penalties later.

Your Medicare checklist should include:

• Make a list of your current medications.
• Check plan formularies (drug lists).
• Compare costs at your preferred pharmacy.

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Step 6: Consider a Medigap (Supplement) Policy

If you choose Original Medicare, you’ll likely want a Medigap policy.

What Medigap Covers

• Pays for out-of-pocket costs like copayments, deductibles, and coinsurance.
• Lets you keep nationwide access to Medicare providers.
• Doesn’t usually include vision, dental, or prescriptions.

Why It Matters

The best time to buy Medigap is during your 6-month Medigap Open Enrollment Period (starts when you’re both 65 and enrolled in Part B). During this time, insurance companies can’t deny you coverage or charge more because of health conditions.

Put this in your Medicare checklist: If Original Medicare is my path, line up a Medigap plan now.

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Step 7: Review Your Doctors and Providers

Healthcare is personal. You want to make sure your doctors, specialists, and hospitals are covered.

Your Medicare checklist should include:

• Ask each doctor: “Do you accept Medicare?”
• If considering Medicare Advantage: check the provider directory.
• If you need specialists (cardiologists, endocrinologists, etc.), confirm they’re included.

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Step 8: Look at Total Costs

Many people focus only on premiums. But your Medicare checklist should cover the big picture:

• Monthly premium
• Annual deductible
• Copayments and coinsurance
• Maximum out-of-pocket limit (on Medicare Advantage plans)
• Prescription drug costs

This is where comparing plans side by side really pays off.

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Step 9: Gather Your Personal Information

Before you apply, have these ready:

• Social Security number.
• Current health insurance details.
• List of prescriptions.
• Preferred doctors and pharmacies.
• Banking info if you want automatic premium payments.

Adding this to your Medicare checklist saves you time and stress during enrollment.

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Step 10: Watch Out for Penalties

Late penalties can stick with you for life:

• Part B Penalty: 10% increase in premium for every 12 months you delay enrollment without creditable coverage.
• Part D Penalty: 1% of the national base premium for each month you go without coverage.

Your Medicare checklist should remind you: Enroll on time or risk paying more forever.

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Step 11: Consider Your Spouse

Medicare is individual coverage—you each enroll separately. If your spouse is younger than 65, you’ll need to plan for their insurance until they qualify. Add this to your checklist if you’re married or in a domestic partnership.

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Step 12: Use Resources and Get Help

Medicare is complicated, and you don’t have to figure it out alone.

Helpful resources include:

• Medicare.gov – official federal website.
• Social Security Administration – to sign up for Parts A and B.
• Statewide Health Insurance Benefits Advisors (SHIBA) in Washington – free counseling.
• Licensed brokers – personalized guidance at no extra cost to you.

Your Medicare checklist should include: Find a trusted advisor before making final decisions.

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Step 13: Think Beyond Medicare

Medicare is the foundation, but you might also need:

• Dental insurance – not covered by Original Medicare.
• Vision insurance – limited coverage unless you have a Medicare Advantage plan.
• Long-term care planning – Medicare doesn’t cover most custodial care.

Add a note to your checklist: Consider add-ons for full protection.

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Step 14: Review Every Year

Your Medicare journey doesn’t end once you enroll. Each year, during Open Enrollment (Oct 15–Dec 7), you can:

• Switch from Original Medicare to Medicare Advantage or vice versa.
• Change Part D prescription drug plans.
• Reevaluate based on new health needs or doctor changes.

Your final Medicare checklist step: Mark your calendar for annual review.

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Putting It All Together: Your Medicare Checklist

Here’s the condensed version you can print out:

1. Learn the basics of Medicare (Parts A, B, C, D).
2. Mark your Initial Enrollment Period.
3. Decide if you need to enroll now or can delay.
4. Compare Original Medicare vs. Medicare Advantage.
5. Choose prescription drug coverage.
6. Consider Medigap if using Original Medicare.
7. Check your doctors and providers.
8. Review total costs, not just premiums.
9. Gather personal info for application.
10. Avoid late enrollment penalties.
11. Consider spouse’s coverage needs.
12. Use trusted resources or brokers.
13. Think about add-ons like dental and vision.
14. Review coverage annually.

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Final Thoughts

Turning 65 doesn’t have to mean drowning in paperwork or making blind choices. With the right Medicare checklist, you’ll have each step laid out, making the process far more manageable. Start early, ask questions, and lean on resources—whether that’s Medicare.gov, SHIBA in Washington, or a licensed broker who can walk you through options.

The bottom line: Medicare is here to protect your health and financial future, but it works best when you prepare. By checking off each step before your 65th birthday, you’ll move into retirement with confidence, clarity, and peace of mind.

Frequently Asked Questions About Preparing for Medicare

When should I start preparing for Medicare?

It’s smart to start preparing about 6–12 months before your 65th birthday. This gives you time to understand the different parts of Medicare, compare options, and make sure you don’t miss your Initial Enrollment Period.

What happens if I miss my Medicare enrollment window?

If you miss your Initial Enrollment Period and don’t qualify for a Special Enrollment Period, you may face permanent late penalties. For Part B, your premium could go up 10% for every 12 months you delayed. For Part D, you’ll pay 1% extra for every month you went without drug coverage.

Do I need to sign up for Medicare if I’m still working at 65?

Not always. If you have employer-sponsored insurance through your job or your spouse’s job, you may be able to delay Part B without penalty. Always confirm with your HR or benefits office because COBRA or retiree coverage may not count as creditable coverage.

What’s the difference between Medicare Advantage and Original Medicare?

Original Medicare includes Part A and Part B, and you can add a Part D plan and possibly a Medigap supplement. Medicare Advantage (Part C) bundles everything into one plan, often including drug coverage and extra benefits, but you’ll usually have a provider network.

Do I need a prescription drug plan if I don’t take medication?

Yes, it’s still recommended. Enrolling in Part D on time helps you avoid future penalties, and it protects you if you need medications later. Plans are structured so even people with few prescriptions can find affordable coverage.

What is Medigap and when should I buy it?

Medigap is supplemental insurance that helps cover deductibles, copays, and coinsurance that Original Medicare doesn’t pay. The best time to buy is during your 6-month Medigap Open Enrollment Period, which starts when you’re 65 and enrolled in Part B. During that time, you can’t be denied coverage.

Will Medicare cover my spouse too?

No, Medicare is individual coverage. Your spouse will only qualify when they turn 65 (or earlier if they meet disability requirements). If your spouse is younger, you’ll need to find them separate coverage until they become eligible.

How much will Medicare cost me each month?

Costs depend on which parts and plans you choose. Part A is usually premium-free, Part B has a standard monthly premium, and Part D or Medicare Advantage plans vary. Higher-income individuals may pay more. Always compare total costs, including deductibles and out-of-pocket maximums.

Does Medicare cover dental and vision?

Original Medicare does not cover routine dental or vision care. Some Medicare Advantage plans include dental and vision benefits. If you want these services, you may need a stand-alone plan or a Medicare Advantage plan that offers them.

Can I change my Medicare plan later?

Yes. Each year, during Open Enrollment (October 15 to December 7), you can switch between Original Medicare and Medicare Advantage, change drug plans, or adjust coverage. It’s a good idea to review your plan every year.