The mail starts arriving about six months before your birthday, and most of it looks urgent. Very little of it is. Here’s the order things actually happen in.
Know your seven-month window
Your Initial Enrollment Period runs for seven months: the three months before the month you turn 65, the month itself, and the three months after. That’s the window to enroll in Medicare without a late penalty.
Signing up in the three months before your birthday month is what gets your coverage started on time. Leave it to the months afterwards and your start date slides, which can leave you with a gap you didn’t plan for.
Work out whether you can delay
This is the question worth answering before any other, because getting it wrong is expensive and permanent.
If you’re still working at 65 and have coverage through that job, you may be able to delay Part B without a penalty, or you may not. It depends on the coverage and on how large the employer is. The same question applies to prescription coverage and Part D.
There’s no way to work this out from a brochure. Call someone, tell them what coverage you have and who you work for, and get a straight answer. If you’d rather that be me, the number’s at the top of this page.
Then, and only then, choose a road
Once you have Parts A and B, you pick one of two approaches: keep Original Medicare and add a Supplement plus a separate drug plan, or get your benefits through a Medicare Advantage plan instead. You can’t hold both.
Which one suits you depends on your doctors, your prescriptions, how much you travel, and what you’d rather pay monthly versus at the point of care. That’s a conversation, not a form, and it’s the part I’d rather you didn’t rush.
What to have in front of you
When you’re ready to talk it through, have these to hand:
- The names of every doctor you see, including specialists
- Your prescriptions, with actual names and doses
- The pharmacy you use
- Whether you have coverage through an employer, a union, or the VA
That’s genuinely everything. Fifteen minutes with that list beats an afternoon of comparing plans on your own.