Are you planning to retire in the next 12 months? If so, now is the perfect time to start planning your Medicare and Retirement strategy. Many people are surprised by how much timing, paperwork, and plan choices can impact their health coverage—and their wallet. Getting ready to retire? What to do about Medicare is a critical consideration. Failing to prepare could lead to lapses in coverage, unexpected penalties, and unnecessary stress.
Let’s walk through the key steps you should take before leaving your employer health plan so you can transition smoothly into the best Medicare plan for your needs.
Step 1: Six Months Before Retirement – Start Researching
About six months before retirement, begin your Medicare plan comparison. This is the time to:
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Confirm which Medicare plans your doctors accept.
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Review your prescriptions and check Medicare coverage for those medications.
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Understand how your income (including severance, Roth conversions, or pension payouts) may affect your Medicare premiums.
Identifying red flags early gives you more time to fix them before your employer coverage ends.
Step 2: Three Months Before Retirement – Get Employer Verification
If you’ve delayed Medicare past 65 because of employer coverage, Medicare requires proof that your plan met their rules. Ask your HR department for an employment verification form confirming that you or your spouse had qualifying coverage.
This document is critical—it prevents late enrollment penalties and ensures a smooth transition.
Step 3: Two to Three Months Before Retirement – Apply for Medicare
Once you have your employer verification, apply for Medicare Part A and Part B. This is especially important if your employer coverage is ending soon.
⚠️ Important: COBRA coverage does not count as creditable coverage for Medicare. Make sure you enroll in Medicare before your employer plan ends to avoid gaps.
Step 4: One to Three Months Before Retirement – Choose Your Coverage
After your Medicare Part A and B applications are processed, it’s time to decide whether to:
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Enroll in a Medicare Advantage plan, or
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Stay on Original Medicare and add a Medigap (Medicare Supplement) and Part D prescription plan.
- Join a retiree health insurance plan
This is where a thorough Medicare plan comparison helps you choose the best fit for your doctors, medications, and budget.
Step 5: Finalize and Pay Premiums
Your last step is simple but critical—set up premium payments for your chosen plan. Many people forget this step and experience a lapse in coverage. Don’t let that be you!
Also, update your providers with your new Medicare information to ensure smooth billing.
Key Takeaways
Preparing for retirement means more than just leaving work—it means making smart decisions about your healthcare. By starting early, gathering the right paperwork, applying on time, and comparing your options, you’ll avoid penalties, lapses in coverage, and costly mistakes. A thoughtful Medicare and Retirement strategy ensures you enjoy peace of mind and financial security.
Get Unbiased Medicare Guidance
The Medicare Coach is not associated with any insurance company, agent, or broker. This means we are completely independent and do not make commissions off recommended plans.
We offer a free online Medicare workshop that has helped over 150,000 people easily make their RIGHT Medicare decision.
To get help with your Medicare decision, you can register for my next free online Medicare workshop by going here: https://join.themedicarecoach.com/free-workshop
Dear Coach,
What if I am not retiring?
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