The mail starts arriving around your 64th birthday and it does not stop. Almost none of it is useful, because none of it knows who your doctors are or what you take.
Here is what actually needs doing, in order.
Six months out — gather and confirm
Confirm whether you will take Part B on time. If you are not working, the answer is yes. If you are working, this is the question that decides everything else:
- Employer with 20 or more employees, creditable coverage: you can usually delay Part B safely and pick up a Special Enrollment Period later.
- Employer with fewer than 20 employees: Medicare typically becomes the primary payer at 65 and delaying can leave you exposed for most of your costs.
Ask your benefits office for a written statement that the plan is creditable coverage for Medicare purposes. Not “is this good coverage” — the specific creditable-coverage determination. That is the thing that protects you.
Work out your dates. Your Initial Enrollment Period is seven months: three before your birthday month, the month itself, three after. If you were born on the first of a month, everything shifts one month earlier. The enrollment window checker does this from your date of birth.
Start the list. Two lists, in fact, and they decide more than anything else you will read:
- Every doctor you want to keep, plus the hospital you would want to use
- Every prescription — name, strength, quantity — read off the bottle, not from memory
If you have an HSA, plan the stop. You cannot contribute to a Health Savings Account while enrolled in any part of Medicare, including premium-free Part A, and Part A can be backdated up to six months when you enroll after 65. Most people need to stop contributions several months before enrollment. Confirm the timing with your tax adviser.
Four months out — make the structural decision
Before you look at a single named plan, decide which of the two structures fits you:
Original Medicare + Medigap + Part D. Any provider in the country who accepts Medicare, no referrals, no prior authorisation, close to nothing at the point of care. Three premiums, and the Medigap premium rises over time.
Medicare Advantage. One plan, one card, usually a $0 plan premium, drug coverage and extras bundled. A network, copays as you use care, and a hard annual out-of-pocket maximum.
The five questions that settle it are in Medicare Advantage vs Medigap. The short version: your doctors, your travel, your budget, your worst-case tolerance, and how you feel about prior authorisation.
Why this order matters
People usually start by comparing named plans, which is like choosing a car before deciding whether you need a car or a van. Decide the structure first. The structure decision is the one that is hard to reverse — leaving Medicare Advantage for a Medigap policy later can require medical underwriting. The plan-within-a-structure decision can be revisited every autumn.
Three months out — file, and shortlist
File for Part A and Part B with the Social Security Administration, online, by phone or in person. If you are already receiving Social Security benefits, this happens automatically and your card arrives around now.
If you are enrolling after 65 having delayed because of employer coverage, you will need form CMS-L564, the request for employment information, completed by your employer. Start that early — HR departments are not always quick.
Shortlist the plans. Then check, plan by plan:
- Is each of your doctors in the network for this specific plan, for the coming plan year?
- Is each of your prescriptions on the formulary, and at what tier?
- Is your pharmacy a preferred pharmacy for this plan?
- What is the out-of-pocket maximum, the specialist copay, and the inpatient cost share?
This is the work. Everything else is packaging.
Two months out — decide and apply
Compare on total cost, not premium. For Part D especially, the plan with the lowest premium is routinely not the cheapest plan for someone taking several medications. Our Part D total cost estimator runs the arithmetic, or send us your list and we will run every plan in your county.
If you are going the Medigap route, apply now. Your six-month Medigap Open Enrollment Period starts when Part B begins, and during it a carrier must issue you any policy it offers regardless of health. Applying early inside the window is straightforward. Waiting until the window has closed can make the policy unobtainable.
Submit the application and get the effective date confirmed by the carrier, not just by the enrollment confirmation screen.
One month out — confirm everything
- Your Medicare card has arrived, with the correct Part A and Part B effective dates
- Your plan card has arrived, or the carrier has confirmed the effective date in writing
- Your pharmacy has the new plan on file — this one prevents a bad morning at the counter
- Your doctors’ offices have the new information
- If you are dropping employer coverage, the termination date lines up with the Medicare start date, with no gap
After you start — the annual habit
The job is not finished at enrollment. Every plan changes on January 1: formularies, tiers, networks, premiums, cost sharing and supplemental benefits.
Each September your carrier mails an Annual Notice of Change. Keep it. Then between October 15 and December 7, re-run your doctors and prescriptions against next year’s plan and against the other options now available in your county. That is what an annual coverage review is, it takes about twenty minutes, and it costs nothing.
The phone call we would most like to prevent is the one in February that starts “I went to pick up my prescription and they wanted four hundred dollars.” That drug moved tiers on January 1, the notice arrived in September, and the window to change closed on December 7.
What to bring when you call us
- Your current insurance card
- The list of doctors and the hospital you want to keep
- Your prescriptions — names, strengths, quantities, from the bottles
- Whether you are still working, and roughly how many employees your employer has
- Whether you travel or spend part of the year in another state
- Roughly what feels comfortable monthly, and what a bad year could look like
That is everything. Book a free consultation or call — there is no fee, and no obligation at the end of it.
Frequently asked questions
When should I start thinking about Medicare?
Six months before your 65th birthday. That gives you time to confirm whether employer coverage is creditable, understand the structural choice, and decide without pressure. Three weeks out means making a decision with a stack of unopened envelopes on the counter.
What should I bring to a Medicare consultation?
Your current insurance card, a list of every doctor and the hospital you want to keep, and your prescriptions with strengths and quantities read straight off the bottles. Whether you are still working and how many employees your employer has. That is enough for a genuinely useful answer in one conversation.
Do I need to do anything if I am already on Social Security?
You will be enrolled in Parts A and B automatically and your card will arrive about three months before your birthday month. You still have to decide what goes alongside it — a Medicare Advantage plan, or a supplement plus a Part D plan — and that decision is not automatic.
How much of the mail I am getting should I read?
Almost none of it. Marketing mail from carriers is not personalised to your doctors or your prescriptions. The envelopes that matter come from Social Security and, once you are enrolled, from your own plan each September. Everything else is advertising.