I’m turning 65. What do I do? |

The answer comes down to one thing: whether a job is still covering you.

If you’re not working

Or you are working, but no job is covering you — same answer here. Two things decide your timing.

Are you already drawing Social Security?

If so, this is mostly done for you. You’re enrolled in Part A and Part B automatically, and your card arrives about three months before your birthday. You’re not signing up for anything — you’re deciding what to add.

Not drawing Social Security yet?

Nothing happens on its own. You have to enroll.

When?

You get a seven-month window: the three months before your birthday month, your birthday month, and the three months after. Sign up before your birthday month and coverage starts the month you turn 65. Wait until your birthday month or later and it starts the first of the next month. If you want coverage in place the day you’re eligible, go early.

How?

Three ways, and they aren’t equal.

Online at ssa.gov is the fastest. Online applications are processed the same as any other and usually move quicker. With your documents in hand it takes about half an hour.

By phone. Social Security is at 1-800-772-1213, weekdays. You can apply on the call or schedule an appointment.

In person is no longer the dependable fallback it once was. Field offices have run on scheduled appointments since 2025, and walk-ins get handled last, if at all. If you want to go in, book it first.

Processing is also slower than it used to be, so whichever route you pick, don’t leave it until the end of your window.

And if you’d rather not do it alone, call us. We walk people through this every week.

After that, you’re at the same decision everyone makes.

Still working?

If so, then maybe nothing.

That isn’t a joke. For a lot of people turning 65, the right move this year is to leave things alone. Almost nobody hears that.

“But, someone told me I have to sign up now or be penalized forever.”

They meant well. They may also be wrong about you — penalties only apply in certain circumstances.

You don’t get penalized for turning 65. You get penalized for going without coverage. Those are two different things, and confusing them is the most expensive mistake we see.

If you or your spouse are still working — and intend to keep working — and you’re on that current job’s group plan, you can very likely stay right where you are, penalty-free, for as long as that coverage lasts. Coverage from a former employer, a retiree plan, or COBRA is not the same thing — those don’t hold the window open.

Signing up anyway can cost you money you never had to spend. In one specific case, it can cost you money your employer was handing you.

Whether that describes you comes down to a few specifics.

The questions that decide it

These don’t have the same answer for everybody. But if you can answer them, you’re most of the way there.

How many people does that employer employ?

The employer that matters is the one currently employing you or your spouse — not a former job. There’s a threshold in the law. On one side of it you can defer safely. On the other, Medicare is supposed to pay first, and skipping it leaves a hole you won’t find until a claim comes back wrong. The count is the whole company, not just your location. Most people guess wrong.

Are you contributing to a health savings account?

You can’t take Part A or Part B and keep contributing to an HSA. Not even the Part A that costs most people nothing. Your contributions stop, and so do your employer’s — which is exactly why the sign-up-at-65 advice can backfire. Part A can also backdate up to six months, so contributions you already made can become a tax problem after the fact. Worth knowing before anyone talks you into signing up.

Is anyone else on your plan?

A younger spouse, a dependent still on your coverage. Their situation can be the whole reason to stay put, and it’s the one people forget to count.

Is the group plan still the better deal?

Sometimes it stops being one. That’s a comparison, not a rule.

Is your income high enough to trigger IRMAA?

Above a certain income, Part B isn’t the standard premium — Medicare adds a surcharge called IRMAA, based on your tax return from two years ago. Someone still working at a strong income is exactly who lands in that range, which can make enrolling now a worse deal than waiting. Worth checking before you sign up for anything.

And then?

Pick up the phone. 281-894-7540.

Not because this is beyond you (you can absolutely do it). But because you can outsource this at no cost to you. We can make this easy and spare you having to learn it all. You let us know what you want and we will help you get it in place (as long as it is possible). One conversation — in person, by phone, or on a video call — and you’ll know exactly which of the above applies to you and what, if anything, you need to do this year.

We’ll be as involved as you want us to be. Two questions or every step. No obligation, and our services are always free to you.

Not connected with or endorsed by the United States government or the federal Medicare program.

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“Just wanted to let everyone know how great you were I needed to change my Medicare health insurance and he went the extra mile for me I would highly recommend him.”

Mark H.- Magnolia, Texas

“Justin is genuinely committed to doing the right thing. He’s honest and has proposed what makes sense for me and my business partner. ”

B.F.- Houston, Texas

“Justin cares for his clients. He took the time to find out my needs & concerns. As a result found exactly what I wanted. I would recommend him to anyone.”

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