Which one are you? Take-Home Notes, part five
October 2, 2026
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Show Notes
Eddie and Betty's Conversation
Welcome to The American Retirement Advisor podcast. I am Betty, and Eddie is here in the studio with me today. We are wrapping up something we have been building toward all week, because Ian Schaeffer just posted part five of the Take-Home Notes from the Medicare workshops, and Eddie, I have to tell you, the way this thing ends is so simple it almost stopped me in my tracks.
Thanks for having me. And yeah, three boxes on a slide. That is the whole finale. Which one are you?
After everything. The two paths, the four words, the Medicare.gov walkthrough, all of it builds to a slide with one question.
And the beautiful thing about it is what comes right after. The article says almost everyone in the room fits one of the three, and each box has its own to-do list. So instead of sitting there taking notes on things that don't apply to you, you find your box and skip the other two.
Which is how it should work. So let's go through the boxes, because I think each one has at least one thing in it that is going to surprise people. What's the first box?
Not on Medicare yet, or still working. And this one splits three different ways depending on your situation, so there's a little more going on here.
Okay, walk me through the still-working piece first, because I feel like a lot of people in their mid-sixties are in that exact spot.
So if you're still on the job and your employer has twenty or more employees, you can stay on the group plan and actually wait on Parts B and D with no penalty. The workshop does the stay-or-go math right there in the room, side by side, so you know to the penny what leaving early costs.
That is a great detail. Not a vague 'it depends,' but actual math in the room.
Right. But there are two warnings that come with that, and I think both of them are the kind of thing people don't know until it's too late.
Okay, I'm listening.
Warning one: COBRA does not count as job coverage once you're eligible for Medicare. The article points to their piece on COBRA and the Medicare clock for the math, but the short version is, if you think COBRA is protecting you from a late enrollment penalty, it is not.
Wait, really? Because so many people assume it's just a continuation of their regular coverage and they're fine.
Completely understandable assumption, and completely wrong in this context. COBRA and job coverage are not the same thing for Medicare purposes.
That is one of those things where I'd want to double-check the specifics with one of our advisors before doing anything, because the stakes are too high to guess.
Agreed. And warning two is about health savings accounts. If you sign up for Part A while you still have an HSA, you lose the ability to keep contributing to it.
So Part A, which most people think costs nothing and is harmless to pick up whenever, has a real cost hiding in it if you've been diligently saving in an HSA.
That's the kind of thing that catches people. You're doing the right thing, you're saving in your HSA, you turn 65, you grab Part A because why not, and suddenly that HSA contribution is off the table.
That one would sting. Okay, what about the people in this first box who are not collecting Social Security yet?
This is the part a lot of folks miss. If you're not yet drawing your benefit, nobody signs you up for Medicare automatically. The handbook Ian Schaeffer quotes is very direct about it. You'll need to sign up yourself, online through the Social Security website, or by calling 1-800-772-1213 for an appointment.
So there's no fairy godmother over there who notices you turned 65 and handles it.
You have to go find the enrollment yourself. And the article adds something I thought was a smart practical tip: keep the application summary you get at the end of that process, because it proves your start dates and your Medicare number.
That's the kind of thing you file in a folder and forget about until you really, really need it.
And then you're very glad you kept it.
Now the flip side: if you are collecting Social Security, it's automatic?
Right, it just kicks in on the first day of the month you turn 65, and the card comes in the mail.
That seems almost too easy compared to what we just described.
It's the one corner of Medicare where the government does the work for you. Enjoy it.
Ha. Okay, let's go to box two: already on an Advantage plan. Because this is one of those situations people get comfortable in and just stop paying attention.
And the article has a very specific thing to say about that. It's not just 'review your plan every year.' It's research it in a set order. Your doctors first, then your hospitals, then your drug costs, and only after all of that do you look at the extras.
The order is the point.
That's literally the phrase Ian Schaeffer uses. Because a plan that has a dental allowance you love is no bargain if your cardiologist is out of network.
That's such a good way to put it. You're excited about the benefit, you pick the plan, and then you find out your specialist won't take it.
People do this. And then they're either stuck with a doctor they didn't want to leave, or they're paying out of pocket for the one they did want.
So doctors first. Always. And then when is the window to actually switch if you're on Advantage?
October 15 through December 7 is the main one. But there's a second that I don't think gets enough attention: January 1 through March 31. If you switch during the fall and then change your mind, you get another shot.
A do-over window. I love that.
The article covered all of that in part three of the notes. We did an episode on it too if people want to go deeper.
Okay, next box: Supplement and Part D. This one I find interesting because the advice is almost the opposite of what I expected.
How so?
Well, I would have assumed if you're on a Supplement you just kind of set it and forget it. But the drug plan piece is not that.
No, the drug plan is math you redo every fall, because those plans can change their lists and their prices every single year. Your drugs, your pharmacy, the total yearly cost. Run the numbers fresh.
So the plan you picked two years ago might not be the best option for the exact same things today.
That's the thing people don't realize. The plan didn't necessarily do anything wrong. The pricing just changed. That's why you check.
And what about the Supplement itself? Can you switch that whenever you want?
You can apply to change it any month of the year, not just in the fall. But here's where it gets interesting: outside your first six months on Part B, health questions may apply.
So there can be underwriting involved once that initial window closes.
The exact rules there are really a conversation for one of our advisors, because it depends on a lot of individual factors. But the article is clear that that initial window we mentioned -- the one where you're protected from health questions -- it matters, and you don't want to sleep through it.
Good to flag. Now there's a line in the article about comparing Supplements that I keep thinking about, because it reframes the whole decision.
The one from Medicare's own booklet?
Yes. Say it.
A Plan G from one company has the same basic benefits as a Plan G from another company. So when you're choosing between Supplement policies with the same letter, the only real difference is price.
That is such a useful thing to know. You don't have to figure out which company has the better Plan G. It's the same coverage, so price becomes the big question.
Which is what the workshop said in part one, and what Medicare's own materials say. Same letter, same benefits, shop around.
Okay, let's talk about the advisor section, because I think this is where the article does something really useful. It gives you six actual questions to ask.
And they're good ones. Not generic 'make sure they're trustworthy' stuff. Specific things you can say out loud in a meeting.
What's your favorite one?
Probably the one about ten companies. Do you offer plans from at least ten different carriers? Because if someone only works with two or three, you're not getting a full picture of what's available in your county.
It's like going to a car dealership that only sells one brand and asking them if that brand is the best car.
They'll say yes every time.
That's the pattern, yeah. What are some of the others on the list?
Are you licensed in my state. Do you have real local people who answer the phone. Can I talk to clients who chose the plan I'm looking at. And will you show me a side-by-side comparison of every plan in my county, not just a few.
That last one is sharp. Not just a few. Show me all of them.
Because a comparison of three plans when there are dozens in your county isn't really a comparison.
And there's one more thing the article pulls from Medicare.gov that I think people should hear, because it's about what agents and plans are not allowed to do.
Charge you a fee to process your enrollment into a plan. Medicare.gov is explicit on that. That is on the list of things plans and the people who work with them cannot do.
So if someone is trying to charge you an enrollment fee, that is a red flag with a siren on top.
Walk away.
Let's zoom back out for a second. Ian Schaeffer is writing this as the workshops are literally happening. The first room was filling at Foothills Library in Glendale, and a second one was opening that afternoon in Scottsdale. There's something I find kind of wonderful about that.
It's a live document. The notes go up while people are still in the seats.
For anyone who didn't make it to Glendale, there's a Scottsdale session coming up. The article mentions Mustang Library, 2:30 PM, at no cost to you. You can register at 123easymedicare.com slash medicare-workshop, or call 877-220-1089.
And the full set of notes is right there in the article series. All five parts, in order.
Part one was the two paths and the foundation. Part two was the four words that decide your bill, copay, deductible, network, maximum out-of-pocket. Part three was every window and what it allows. Part four was Medicare.gov live, searching the 2027 plans step by step.
And part five, what we're talking about today, is the landing. Circle your box, write one next step, put a date next to it.
A date. Not 'I'll get to this.' A date.
And the article points out that for most people reading this in October, that date falls somewhere between October 15 and December 7. Which is the Annual Enrollment Period. Which is just around the corner.
So the urgency is real. This isn't a someday thing.
It doesn't exist on the Medicare calendar.
Ha. I'm putting that on a mug. Okay, before we wrap, let's do a fast pass. What are the two or three things you'd want someone to walk away remembering from today?
And that COBRA trap we flagged earlier is a real gut punch when people find out the hard way. It's the kind of mistake that follows you straight to your wallet. Find your box, not someone else's box, because the to-do lists are completely different. And if you're on Advantage, research in order: doctors, hospitals, drugs, then extras.
And I'd add: the person helping you shouldn't be charging you to enroll. If they are, that's a problem.
Good one to add.
The article also has the team's phone number for questions: 602-281-3898. And I'd say, if anything we talked about today made you realize you're not quite sure what box you're in, or your situation feels more complicated than the three boxes cover, that is the moment to sit down with an advisor.
Not a search engine. A person who knows your situation.
Exactly the right call. The full notes are at the article, all five parts are there waiting for you, and the podcast episodes go alongside them if you're more of a listener than a reader. Which, since you're here, I suspect you might be.
A reasonable suspicion.
Thank you all so much for spending this time with us. Go find your box, write that one next step, and put a real date next to it. That's the whole assignment.