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Medicare 101

Your Turning 65 checklist

Posted June 13, 2026

Turning 65 comes with a to-do list nobody hands you. Here’s the short version, in the order it tends to matter.

About 3 months before your birthday

  • Mark your enrollment window. Your Initial Enrollment Period is 7 months long, the 3 months before your birthday month, your birthday month, and the 3 months after. Signing up early means coverage can start right on time.
  • Check how you’ll get Part A and Part B. If you’re already drawing Social Security, you may be enrolled automatically. If not, you’ll likely need to sign up yourself.
  • Think about whether you’re still working. If you (or your spouse) have solid coverage through a current job, the rules are a little different, and you may be able to delay without a penalty. Ask about this before you do anything.

Around your birthday month

  • Make your big choice. Original Medicare with a Supplement and a drug plan, or a Medicare Advantage plan? This is the fork worth slowing down for.
  • List your doctors and prescriptions. The right plan depends on them. Bring the actual names, it makes everything easier.
  • Mind the Medigap window. If you’re leaning toward a Medicare Supplement, your best one-time window to buy one regardless of health opens when your Part B starts. It’s worth not missing.

After you’re enrolled

  • Keep your paperwork. Your Medicare card and plan details in one spot saves headaches later.
  • Put one date on the calendar: the fall Annual Enrollment Period, October 15 to December 7, when you can review and change your coverage for the next year.
  • Know who to call. When a bill looks wrong or your prescriptions change, you shouldn’t have to figure it out alone.

The one tip I give everyone

Don’t wait until the last week. The choices aren’t hard once someone walks you through them, but they’re a lot easier with a little runway. If you’re three to six months out, that’s the perfect time to talk.

Want me to walk the checklist with you? Call or text, it’s free, and there’s no pressure. Official details live at Medicare.gov or 1-800-MEDICARE.

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