The MedicarePROFESSOR
EnrollmentMarch 5, 2026

Turning 65 This Year? Your Month-by-Month Checklist

Exactly what to do starting 6 months before your birthday, so nothing slips and no penalty follows you.

Turning 65 is not just a birthday. It is the start of a series of Medicare deadlines that, if missed, can cost you money for the rest of your life. The good news: with a simple month-by-month plan, you can avoid every penalty, keep your doctors, and land in the right plan without the stress.

1
6 months before

Research your options

  • Learn the four parts of Medicare: A, B, C, and D
  • Understand the difference between Advantage and Medigap
  • Start gathering your doctors, specialists, and medication list
  • Determine if your employer coverage continues past 65
2
3 months before

Apply for Medicare

  • Enroll in Medicare Part A and Part B (if not automatic)
  • Decide whether to keep employer coverage or switch to Medicare
  • If switching, choose a Medigap plan during your 6-month Open Enrollment Period
  • Select a Part D drug plan or confirm your Advantage plan includes drug coverage
3
1 month before

Confirm enrollment

  • Verify your Medicare card arrives with the correct effective date
  • Confirm your chosen plan is active and your premium is set up
  • Schedule any preventive screenings covered under Medicare
  • Contact your doctors to confirm they accept Medicare or your new plan
4
After your birthday

Stay on track

  • Review your Annual Notice of Change letter every fall
  • Mark October 15 to December 7 on your calendar: Annual Enrollment Period
  • Keep your medication list updated for annual plan reviews
  • Call us with any questions — we are here all year, not just at enrollment

The one thing to never skip

Your Initial Enrollment Period is the 7-month window around your 65th birthday — 3 months before, your birthday month, and 3 months after. If you miss it, you may face a lifetime late enrollment penalty on your Part B premium of 10% for every 12-month period you were eligible but did not enroll. That penalty never goes away.

Turning 65 soon? We make it simple.

A free review walks through every deadline, every option, and every number. Nothing slips.

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