Medicare is one of the most important financial decisions you'll ever make — and most people approach it for the first time with about a week's worth of preparation. Here's how to do it the right way, starting 6 months before your 65th birthday. Follow this and you'll lock in the best rates, avoid the late-enrollment penalties, and pick the right plan the first time.
6 months before your 65th birthday
This is the time to start understanding the landscape — not enrolling, just learning.
- Decide whether you'll keep working past 65. If you (or your spouse) have employer-sponsored insurance with 20+ employees, you can usually delay Part B without penalty. If you're retiring, you'll want to enroll on time.
- Check Social Security status. If you've started Social Security before 65, you'll be automatically enrolled in Parts A and B. If not, you'll need to actively enroll.
- Order a copy of your prescription list. Get the actual names, dosages, and quantities of every prescription you take. You'll need this for Part D plan comparison.
- Make a list of your doctors and hospitals. Especially specialists and any hospital you'd want to use in an emergency.
4-5 months before
This is when you start having real conversations.
- Talk to an independent agent. Not a captive carrier rep, not a TV-ad lead generator — an independent agent who can compare every carrier and isn't pushing one specific plan. A 20-minute call now saves dozens of hours later.
- Decide: Original Medicare + Supplement, or Medicare Advantage? This is the biggest fork in the road. Each has trade-offs. Don't pick one because TV ads told you to.
- Read your employer's retiree benefits letter (if applicable). Some employers offer retiree health benefits that interact with Medicare — important to factor in.
3 months before
Your Initial Enrollment Period opens.
- Enroll in Medicare Parts A and B. Sign up at SSA.gov or by calling Social Security. To have coverage start the month you turn 65, enroll during one of these 3 months.
- Get a comparative quote on Medicare Supplements. The 6 months starting the month you turn 65 are your guaranteed-issue window — no health questions, no rejections. This is the cheapest Medigap policy you'll ever buy.
- Or get an Advantage plan comparison. If you've decided to go the Advantage route, this is the time to compare plans in your zip code, check that your doctors are in-network, and verify your prescriptions are on the formulary at a reasonable tier.
1-2 months before
Time to lock things in.
- Submit your Medigap application (if going that route). Carriers typically process in 2-3 weeks; the policy starts the month you turn 65.
- Choose your Part D drug plan if you're going with Original Medicare + Supplement. (Most Advantage plans include drug coverage built in.)
- Cancel any duplicate or unnecessary coverage. If you had a Marketplace plan or COBRA, you'll typically drop it the day Medicare kicks in.
The month you turn 65
- Confirm your Medicare card has arrived. Real Medicare cards come from CMS, are red/white/blue, and have only your name and Medicare number on them. Anything else is a scam.
- Confirm your Medigap or Advantage plan is active by logging into the carrier's portal or calling.
- Take the new card to your next doctor's appointment. The doctor's office will update your file.
Common mistakes to avoid
- Waiting until the last minute — applications can take 30+ days to process, and starting late means a gap in coverage.
- Picking a plan based on TV ads — the celebrity-endorsed plans are rarely the best plan for your specific situation.
- Skipping Part D thinking you don't need it — even if you take no prescriptions now, you'll owe a permanent late enrollment penalty if you sign up later.
- Not checking that your doctors are in the Advantage plan's network before enrolling.
- Buying a Supplement based on premium alone — carrier rate history matters as much as today's price.
One more thing: your spouse
If you and your spouse are both approaching 65, you'll often want different plans. Your respective doctors, prescriptions, and health needs aren't identical. Avoid the temptation to pick "the same plan" for both of you — pick the right plan for each of you separately.