Twelve weeks out is the right time to start. Not six months, when nothing can be done yet and everything you learn will have changed. Not three weeks, when the good options need more time than you have. Twelve weeks.
Here is what actually needs to happen, in the order it needs to happen in. Two of these are routinely done backwards, and I have marked which.
Week 12: answer the employer question
Everything else depends on this, so do it first and do it properly. Will you, or your spouse, still have health coverage from active employment after you turn 65? And does that employer have twenty or more employees?
If yes to both, you can usually delay Part B without penalty and pick it up later through a Special Enrollment Period. If the employer is smaller than twenty people, Medicare generally needs to be primary from 65, and delaying can leave claims unpaid.
Call your benefits office and ask them to put the answer in an email. Not because they will get it wrong, but because in four years, if a penalty is ever proposed, that email is the evidence.
Two things people get wrong here. COBRA does not count as active employment coverage. Retiree coverage usually does not either. Both feel like insurance and neither buys you a delay.
Week 11: if you are stopping work, apply for Part A and Part B
Your Initial Enrollment Period is seven months: the three months before the month you turn 65, that month, and the three after. Apply in the first three and your coverage starts on the first day of your birthday month. Apply later and it starts the first of the month after you apply.
You do this through Social Security, at ssa.gov or by phone. It takes about fifteen minutes and no agent can do it for you, including us. If you are already drawing Social Security, it happens automatically and the card arrives in the mail.
One thing to sort out first if it applies: stop contributing to a health savings account six months before Part A starts. Part A can be backdated up to six months, which can make contributions you have already made ineligible.
Week 10: make the list
Two columns on one sheet of paper. On the left, every doctor you want to keep, including the ones you see once a year. On the right, every medication, with its strength and how often you take it, copied off the bottle rather than from memory.
This list is the input to every honest comparison anyone can do for you. Without it, all anyone can tell you is which plan has the lowest premium, which is very nearly useless information.
Weeks 9 and 8: decide the shape
Now the real decision, and it is one decision, not many. Original Medicare with a Medigap policy and a separate drug plan, or a Medicare Advantage plan.
Supplement route: higher every month, any doctor in the country who takes Medicare, no referrals, no approvals in advance, and a year you can predict almost to the dollar.
Advantage route: much lower every month, often with drugs and dental included, a local network to stay inside, some things needing approval first, and a yearly ceiling on what a bad year can cost.
Neither is better in the abstract. The honest question is where you would rather carry the risk: spread evenly across twelve months, or concentrated in the years when you are ill. The full comparison is here.
Weeks 7 to 5: if you chose a supplement, apply inside the window
This is the first thing people do in the wrong order.
Your six-month Medigap open enrollment begins when you are both 65 and enrolled in Part B. Inside it, no company may refuse you or charge you more because of your health. Outside it, in most states, they may do both, and the window does not come back.
People treat the supplement as the relaxed part of the process because it is standardized and easy to compare. It is the part with the hard deadline.
Weeks 4 to 3: choose the drug plan on the yearly total
This is the second thing people do in the wrong order.
Not the monthly premium. Run your real prescription list against every plan sold in your county, at the pharmacy you actually use, and total all twelve months.
A $0 plan that puts one of your drugs in tier 4 can cost thousands more across a year than a $40 plan that has it in tier 2. The premium is the smallest number in the calculation. Here is how to check a drug list yourself.
And if you take nothing at all, still buy the cheapest plan in the county. Going without means a penalty of 1% of the national base premium for every month you waited, added to your premium for as long as you have Part D. Forever is a long time to save four dollars a month.
Week 1: check the card, then book the free visit
When the card comes, read the effective dates and make sure they are what you expected. If they are not, that is fixable, but only if somebody notices.
Then book your Welcome to Medicare visit. It is free in your first twelve months on Part B, it sets a baseline, and after the first year it becomes the annual wellness visit, which is also free. A surprising number of people never take either.
Then, every fall
Between October 15 and December 7, check again. Drug lists, networks, copays and premiums all change on January 1, and the letter announcing it does not lead with the part that affects you.
That is the whole thing. Twelve weeks, seven tasks, and the two that matter most are the two people leave until last. The checklist version is here, and you are always welcome to call instead.