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More than 2,000 of you have already checked in for enrollment season. Thank you.

September 6, 2026

Show Notes

Eddie and Betty's Conversation

Betty

Welcome back to The American Retirement Advisor. I'm Betty, and Eddie's here with me in the studio today, and we are talking about something that honestly affects every single one of our listeners who is on Medicare or heading toward it. It's about this time of year, this window we're coming up on, and what you actually need to do right now to make sure October and December don't catch you off guard. Eddie, we're pulling from a piece that Ian Schaeffer, the company's COO, wrote over the long weekend, and when I read it I thought, this is the episode we need to make.

Eddie

Yeah, thanks for having me, and Ian's piece is a good one to dig into because it's framed as a thank-you note to the client care team, but tucked inside it is actually a really clear explanation of how the whole Medicare review process works and why the timing matters so much. So I want to make sure people hear that part.

Betty

Let's start with what triggered the piece. Ian mentions that over the last couple of weeks more than two thousand clients completed something called a check-in. What is that?

Eddie

So what it is, is a short review that you get access to through a personal link that was emailed to you. You click the link, confirm your date of birth, and then you're looking at a quick summary of your information on file. Your doctors, your prescriptions, your pharmacy, your phone number, your address. You look it over, fix anything that's changed since last year, hit submit, and you're done. Ian says most people finish it in a few minutes.

Betty

Two thousand of them, and they've already done it. That's a lot of moving quickly on something like this.

Eddie

It is, and that number clearly meant a lot to Ian. He makes a point in the piece of saying it sounds like housekeeping but it is not housekeeping. And I think that's worth sitting with for a second, because I suspect a lot of people, when they get an email asking them to confirm their address and their doctors, think, oh this is just administrative stuff, I'll get to it. But the reason it's not just housekeeping is what it sets in motion on the back end.

Betty

Walk us through what actually happens after someone submits that check-in, because I don't think most people have any idea.

Eddie

So here's the sequence. Every year on October 1st, the official plan information for the following year gets released. That's when the insurers have to publish what their plans look like for 2027, what's covered, what it costs. Then two weeks later, on October 15th, the Annual Enrollment Period opens. That window runs through December 7th. And during those roughly seven weeks, just about everyone on Medicare has the opportunity to decide whether to stay on their current plan or switch to something else.

Betty

So it's a fixed window. You can't just shop around in February.

Eddie

Right, there are specific enrollment periods and rules governing when you can make changes, and outside of certain qualifying circumstances, you're working within that October 15 to December 7 window for coverage that starts the following January. So the stakes of those seven weeks are high. And what Ian describes is that during that period, the advisors take each client's check-in, line it up against every plan available to that person for 2027, and check two things. Are your doctors in the plan's network, and are your prescriptions covered at a price that makes sense for you.

Betty

Those two things. It sounds almost too simple when you say it that way.

Eddie

It's deceptively easy to say, but when you think about how many plans are out there, how different the formularies are, how networks vary even within the same insurance company depending on the plan version, doing that comparison accurately for a real person with real doctors and real prescriptions is not a quick job. And then after that research is done, the client gets a recommendation. Either stay on your current plan, or here is something better and here is exactly why. That last part, the why, is important. It's not just a number, it's an explanation.

Betty

So the check-in is really the raw material the advisors need to do that work. Without it, what are they working from?

Eddie

That's exactly the problem Ian names. He says they cannot do that homework with last year's doctor list. They cannot do it with a prescription that was added in March and never mentioned to anyone. And think about how often that happens. Someone started a new medication after their last check-up. They switched primary care doctors. They moved. They changed pharmacies. All of that matters when you're trying to figure out whether a plan is actually going to work for that person next year.

Betty

I've heard from so many people who had a plan that looked fine on paper and then they showed up at the pharmacy and the drug they needed wasn't covered the way they expected, or they called their doctor's office and found out their doctor wasn't in the network anymore.

Eddie

And those surprises are almost always downstream of not having current information at the time the plan was selected. The whole point of the check-in is to close that gap. And there's also a timing dimension here that Ian mentions that I think is easy to miss. He says the earlier you hand over the current facts, the earlier the research gets done, and the earlier you know what to do when the season opens. So you don't want to submit your check-in on December 5th and expect a thorough analysis by December 7th.

Betty

That makes sense. You're basically helping them help you by not waiting until the last minute.

Eddie

Exactly. And more than two thousand people doing this already, before the enrollment period even opens, means those folks are going to have their homework done and in front of them when October 15th arrives. That's a very different experience than scrambling in November.

Betty

Now, the heart of Ian's piece, and he says as much, is actually a thank-you to the client care team. And I want to spend some time there because what he describes them doing is a lot more than just managing a link.

Eddie

Yeah, he really goes into detail, and I think it's worth reading between the lines a little. He lists out what the team has been doing: answering phones when a link wouldn't open, walking people through it one screen at a time, chasing down emails that bounced, fixing a misspelled last name that was stopping someone from even getting through the door. And then he mentions something that I thought was significant. They're working through a list of clients who don't use email at all, so that nobody gets left out.

Betty

That one stopped me. Because there's a whole segment of the Medicare population for whom that just isn't the primary way they communicate. And it would be very easy to design a system and then just... not follow up with people who didn't respond.

Eddie

And that's clearly not what's happening here. Someone is working that list. And then the last thing Ian mentions is that the team has been flagging situations that needed an advisor's eyes before the enrollment season even starts. So if something in a check-in raises a flag, it's not sitting in a queue waiting for October. It's being looked at now.

Betty

What kind of thing might that be? What would trip that flag?

Eddie

Ian doesn't go into specifics on that, and I wouldn't want to guess at the particulars, because that's really a question for one of the advisors who's doing that triage. But the fact that there's a proactive escalation path built into the process, that's meaningful. It means the check-in isn't just feeding into a spreadsheet somewhere. There are actual human eyes on it.

Betty

Ian calls it the job the loud commercials never mention. And that phrase stuck with me, because if you've ever watched television in October and November you know how saturated it gets with Medicare advertising. It's overwhelming. And what he's pointing to is something completely different from any of that.

Eddie

Because the commercials are selling. What he's describing is servicing. And those are two very distinct activities. The commercials want you to call a number and pick something. The process Ian is describing is designed to make sure that whatever you end up with is built on your real life, not on a generic pitch. That's the phrase he uses, built on your real life instead of a guess. And I think that's the whole thesis of the piece.

Betty

Let's talk about the listener who is sitting there going, okay, I got that email but I'm not sure, or I definitely got it and I haven't clicked it yet. What do they need to do?

Eddie

Ian covers this directly and it's pretty straightforward. First, look for the message from American Retirement Advisors. It has a personal link in it. If you're not seeing it in your inbox, check your spam folder. He specifically calls that out because it happens. Messages from services like this do sometimes end up in spam.

Betty

And if you still can't find it?

Eddie

Call the office. The number Ian gives is 602-281-3898. Client care will send the link again. And if you want someone on the phone while you're actually going through the check-in, same number. They'll walk you through it step by step. So there's no situation where a client should be stuck.

Betty

And what Ian frames it as is, ten minutes now, a recommendation you can trust in October, and a December where nothing sneaks up on you. I love the way he put that. A December where nothing sneaks up on you.

Eddie

And that deadline has a way of arriving faster than people expect. If you've done the check-in early, and the advisors have done the research, and you have a clear recommendation in front of you, the seventh is just a date on the calendar. If you haven't, it can become a scramble. And scrambling on Medicare decisions isn't a great way to make them.

Betty

Let's come back to the two thousand number for a second, because I think there's something important in that for people who haven't done it yet. Ian thanks them, he calls them the people who went first. What does it mean to be a client who goes first?

Eddie

In practical terms it means you're at the front of the research queue. The earlier the information is in, the more time the advisors have to work through it carefully. And when the official plan information drops on October 1st, they're not starting from scratch with you, they already have your current picture. They can run that comparison and get back to you early in the enrollment window, when you have time to ask questions and think it through, rather than late in the window when you're making decisions under pressure.

Betty

There's also something to be said for just having it done. I think a lot of people carry this background anxiety this time of year about Medicare, about whether they're on the right plan, whether something changed that they missed. And completing the check-in is at least one concrete thing you can do to move that forward.

Eddie

The anxiety is real and it's not irrational, because the consequences of being on the wrong plan can be significant. A medication that isn't covered the way you expected, a doctor visit that costs more than you budgeted for, those aren't abstract concerns. So handing your current information to people whose job is to make sure the plan fits you, and doing it early, is genuinely a productive way to spend ten minutes.

Betty

One thing I want to name for people who are maybe newer to this whole process, because Ian writes for people who are already clients and already on Medicare. But we have listeners who are approaching Medicare, maybe they're 63 or 64, and this is all somewhat foreign to them. Does the kind of process Ian's describing apply to them too?

Eddie

The specific check-in he's talking about is for current clients who are already in the Medicare system, so the annual review and the Annual Enrollment Period mechanics are specific to that population. But the underlying principle, that any good Medicare guidance has to be built on your actual doctors and your actual prescriptions and your actual situation, that applies to everyone who will ever be on Medicare. If you're approaching it for the first time, the specifics of when and how you engage that process are a little different, and that's honestly a question for one of the advisors to walk through with you directly, because the rules around initial enrollment have their own timing and their own stakes.

Betty

That's a good point. And the phone number Ian gives, 602-281-3898, that's a real human being at the other end of the line whether you're a current client or someone who's just trying to figure out what questions to even ask.

Eddie

Right. And Ian's whole piece is, in a sense, a reminder that the human being at the end of the line matters. He writes about the client care team doing this work quietly, every day, and that word quietly is deliberate. It's not flashy work. It's all the stuff we were just talking about, the bounced emails, the misspelled names, the painstaking screen-by-screen hand-holding to get someone through a form. None of that ends up in a commercial. But it is the thing that makes the difference between a recommendation built on real information and one built on a guess.

Betty

Let's talk about what's at stake if you don't do this. And I don't mean that in a scary way. I just think it's useful to be concrete.

Eddie

Those two tests Betty just walked through -- the network check and the prescription check -- that's really the whole ballgame. If either one of those fails you in January, you're not in a position to just back out. You're locked into that plan until the next enrollment window opens up. You don't get to swap out because the drug costs hit different than you expected. You are in it for the year. So everything -- the check-in, the research, the recommendation -- all of it is working toward one thing: making sure you don't wake up in 2027 stuck in a plan that was never really built for you.

Betty

And that scenario, starting the year and realizing the plan doesn't fit, happens to real people every year.

Eddie

It does. Not because they were careless. Often because their situation changed and nobody updated the picture before the decision was made. A new prescription, a new doctor, a move to a different part of town. Any of those can quietly shift which plan is the best fit. And if no one asks the question before enrollment, you can end up in a plan that made sense last year but doesn't make sense this year.

Betty

That's such a good frame for why this matters. It's not that the plan you chose was wrong when you chose it. It's that things change and the plan needs to reflect your current life.

Eddie

And the check-in is literally the mechanism for making that happen. It is you saying, here is my current life, now tell me if the plan still fits. That's the whole transaction.

Betty

There's one more thing I want to highlight from Ian's piece, and it's something he says almost in passing but I think it deserves more attention. He comes back to that idea we touched on earlier, the one about guesswork versus something grounded in who you actually are, and he's pretty clear that the recommendation clients get flows from the real picture, not a placeholder. And that word, guess, is doing a lot of work.

Eddie

It is. Because a lot of Medicare guidance that people encounter, whether it's from a television commercial, or a mailer, or a well-meaning family member, is by definition generic. It's built on assumptions about what a typical person on Medicare needs. And your situation is not the average situation. Your doctors are specific people. Your prescriptions are specific drugs with specific costs on specific formularies. The only way to give you a real recommendation is to actually know those specifics. And you have to provide them.

Betty

Which is why, when someone gets that email and thinks, this is just confirming my address, it's worth pausing and recognizing it's actually more than that.

Eddie

It's more than that. It's the first step in a process that ends with you knowing, when December rolls around, whether to stay put or make a change and why. That's a lot of value for ten minutes of your time.

Betty

Let me ask you something that I think listeners wonder about, because this show is about retirement broadly and Medicare is one piece of a bigger picture. How does getting the Medicare piece right fit into the larger financial picture in retirement?

Eddie

Healthcare costs are one of the biggest and least predictable expenses in retirement. And Medicare is the structure you're working within for most of that. If your coverage isn't well matched to what you actually need, you can end up paying more out of pocket than you budgeted for, or making decisions about care based on cost rather than what's medically right. Getting the plan right, keeping it right year over year as your needs change, that's not a side issue in retirement planning. For a lot of people it's one of the most financially consequential decisions they make each year.

Betty

And yet it's something so many treat as less important than, say, their investment accounts, maybe because it feels more complicated or less familiar.

Eddie

The complexity is real. Ian actually mentions in the piece that he's going to talk about this, about why choosing a Medicare plan feels so much harder than it did picking a plan through an employer. And that's a real phenomenon. When you're working, your employer narrows the choices, often covers a significant portion of the cost, and the HR department is there to walk you through it. In retirement you're doing that work yourself with a much wider field of options. It's legitimately more complex.

Betty

Which is part of why having a team that does this specifically for you matters. Not just a comparison website, not just a call center that's going to read you a script, but people who know your information and apply it to your options.

Eddie

And who are, as Ian puts it, doing that work quietly every day. The check-in isn't the whole of it. It's the front door. What happens after, the research, the comparison, the recommendation, that's the work that actually protects you.

Betty

Let's make sure we leave our listeners with a very clear action step, because I think that's what Ian's piece is ultimately pointing toward.

Eddie

So if you're a client of American Retirement Advisors, that email with your personal link -- it went out in the last couple of weeks, so keep an eye out for it. If you spot it, just click it and go through the check-in. Takes a few minutes, pretty straightforward. If you can't find it, check spam first, that's where it likes to hide. And if it's not there either, just call the number Betty already gave you. They'll get that link over to you directly -- and like she said, if you want a real person on the line while you're actually doing it, that same call gets you there. Nobody has to white-knuckle their way through this alone.

Betty

And if you're not yet a client but you're listening and thinking, I want exactly this kind of support going into Medicare season, that phone number is still the right starting point.

Eddie

Real people pick up that line. That's what Ian's making clear. A link doesn't help two thousand people by itself. There are people behind it.

Betty

I think that's what makes Ian's piece worth reading past the headline. It's not really about a form or a link or even the enrollment period. It's about the fact that Medicare, done well, requires someone who knows you. Not a mailer addressed to Current Resident. Not a commercial promising benefits most people don't qualify for. Someone who has your actual doctor's name and your actual prescriptions and who runs the actual math before October 15th so you're not guessing your way through December. If that's not something you have in your corner yet, please reach out. Call 602-281-3898, and have a real conversation with someone whose job is to get this right for you. That's what this whole thing is for.

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