Medicare
Turning 65 in the Midwest: A Month-by-Month Medicare Checklist
Exactly what to do in the three months before, the month of, and the three months after your 65th birthday to enroll in Medicare without penalties.
July 5, 2026 6 min readBy Elie Ortiz
Turning 65 triggers a seven-month Initial Enrollment Period for Medicare. Miss it and you could face lifetime late-enrollment penalties on Part B and Part D. Here's how to stay on track.
3 months before your birthday month
- Decide whether you'll keep employer coverage or move to Medicare
- Request your Medicare card if you're already receiving Social Security (automatic) or apply at ssa.gov
- Compare Medicare Advantage vs. Medigap options for your ZIP code
- Gather your prescription list for Part D planning
Your birthday month
- Confirm your Part A and Part B effective date
- Enroll in a Medicare Advantage plan OR a Medigap + Part D combination
- If keeping employer coverage, get written confirmation it's "creditable"
3 months after your birthday month
- Verify your first premium was drawn correctly
- Set up your MyMedicare.gov account
- Schedule your "Welcome to Medicare" preventive visit
Working with a local independent agent costs you nothing and can save you from costly mistakes.
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