Getting The Most Out Of Medicare: The Deadlines You Can’t Miss And The Decisions You Can’t Afford To Get Wrong
If you’ve ever tried to make sense of Medicare and ended up more confused than when you started, you’re not alone. Between the parts, the plans and the deadlines, it’s easy to make costly mistakes without even realizing it.
On a special episode of the HerMoney Podcast, sponsored by LIMRA, Jean sat down with mother-daughter Medicare experts Diane Omdahl and Melinda Caughill of 65 Incorporated to break down exactly what you need to know – including when to enroll and how to choose between Original Medicare and Medicare Advantage. Here’s what we learned.
MAKING SENSE OF MEDICARE BASICS
At its core, Medicare is government-provided healthcare for people who are 65 or older (or younger if you have a disability or certain conditions).
The only people who are enrolled automatically are those receiving Social Security benefits before age 65. If that’s you, you can expect to get a Medicare card in the mail. Everyone else has to take action. Your initial enrollment period begins three months before your birth month (four months if your birthday falls on the first of the month).
But don’t wait for that window to open. Omdahl suggests starting the real prep six months before your 65th birthday. “We always tell everybody, start as soon as you’re able to,” she stresses. “And that means that before your initial enrollment period starts, you need to begin your preparation and your homework so that you can make your own smart decisions.”
THE ALPHABET SOUP: PARTS A THROUGH D
Medicare comes in parts, and knowing what each one covers is half the battle:
- Part A: Hospital coverage. There’s no monthly premium if you (or your spouse) paid FICA taxes for 10+ years.
- Part B: Medical insurance. This part has a monthly premium that can change each year. For 2026, it begins at $202.90 per month for most beneficiaries, but it may be higher depending on your income.
- Part C: Medicare Advantage (which we’ll cover in further detail below).
- Part D: Prescription drug coverage. Monthly premiums vary based on which plan you join.
THE IMPORTANCE OF A SUPPLEMENT
If you go the Original Medicare route (as opposed to Medicare Advantage), you’ll likely want Medicare Supplement Insurance – also called Medigap. This is extra insurance you buy from a private company to cover what Original Medicare doesn’t – for example, copays, coinsurance and deductibles. “With a supplement, your costs are very predictable,” Omdahl says. “We encourage everybody who goes with Original Medicare to get one because otherwise your costs would be unpredictable and unexpected with no limit.”
Most states offer 10 Medigap plan types. They’re all standardized, meaning a given plan letter offers the same basic benefits no matter where you live or what company sells it – price is the only variable. Plan G is generally considered the most comprehensive for new enrollees. If the premium feels steep, Plan N is a popular, lower-cost alternative.
ORIGINAL MEDICARE VS. MEDICARE ADVANTAGE: NIGHT AND DAY
Deciding between Original Medicare and Medicare Advantage is where many people get stuck — and with good reason. As Omdahl puts it, the two paths are “night and day.” “Part A, B, and D are basically set up and controlled by the government – you know what you’re getting into. You pay a monthly premium; you have predictable out-of-pocket costs,” she explains. And with healthcare costs being a major concern for retirees, knowing what to expect — and planning for those expenses — is key.
Medicare Advantage plans, on the other hand, are run by private insurers who set their own rules. While these plans are typically the cheaper option up front, they come with network restrictions. For example, your doctor might recommend a treatment, but your insurer ultimately decides whether it’s covered. And the doctors you want to see may or may not accept your coverage. “[You have] predictable care with Original Medicare, very few coverage rules…you don’t deal with networks,” adds Omdahl. “Then you get into Medicare Advantage and you have networks, you have prior authorizations and an unpredictable kind of cost.”
For many, the decision comes down to risk tolerance and health – not just today’s health, but tomorrow’s, too. “At some point, our health changes from healthy to not so healthy or not healthy at all; you may not be able to change the type of coverage you have later in life,” cautions Caughill. “You need to be aware that you are making the decision not just for when you are healthy, but when you are potentially no longer healthy.”
BE CAREFUL: THERE MAY BE NO DO-OVERS
Although you can always switch from Original Medicare with a supplement to Medicare Advantage, the reverse isn’t always an available option. As Omdahl explains, those buying a Medigap policy get a one-time, six-month window to do so, which begins once you’re at least 65 and enrolled in Medicare Part B. You’ll need Part A too in order to buy a Medigap policy at all, but it’s your Part B enrollment date specifically that starts the clock – so if you delay Part B because you’re still working and have employer coverage, your window doesn’t open until you actually sign up for Part B.
During that window, any Medigap plan in your area has to accept you, with no medical history questions asked. Once you’ve decided, you’re locked in, and while certain life events can trigger a special enrollment period, most states allow insurers to consider your medical history before approving you outside those windows. This can make it difficult – and in some cases, impossible – for certain applicants to enroll in new Medigap coverage if they have pre-existing medical conditions.
OPEN ENROLLMENT IS COMING: HERE’S YOUR GAME PLAN
Mark your calendar: open enrollment runs October 15 through December 7, giving you the chance to make changes to your Medicare coverage.
Even if you’re happy with your current coverage, Omdahl and Caughill say you need to carefully review your plans each year. Formularies (the list of drugs your plan may cover) can change. Doctors move in and out of networks. Once new plans roll out in early October, it’s time to compare – but give it a beat. “We tell people to pay attention toward the end of October to give the plans a chance to get all the information right… and then compare,” Omdahl suggests. “Is there a better pharmacy? Are my drugs still all covered? What about my doctors?”
One tool that can simplify the prescription drug coverage side of things? HeyMOE, a service created by Omdahl and Caughill that, for $30 a year, automatically helps people compare Part D plans. “HeyMOE automatically remembers when Medicare open enrollment begins and on the first day, it is automatically going to go out and compare all your Part D drug plans,” explains Caughill. “Then, it’s going to reach out to you automatically and say, ‘Hey, we just ran your Part D drug plan options for the next year. It looks like you could save $1,500 by making some changes.’”
FEELING OVERWHELMED? REMEMBER THIS
If Medicare has you spiraling, Caughill offers this advice: “My golden rule is this: the only thing in Medicare that is true for everyone is that nothing in Medicare is true for everyone,” she says. “There are always exceptions. You need to take a good look at your own situation, your own healthcare needs, your own doctors, your own financial situation, and make the decisions that are best for you.”
Also, whatever you do, don’t wait until the last minute. “The biggest mess we tend to deal with with our clients is that they run up against a deadline,” says Omdahl. “They didn’t want to deal with it, they were too busy, they forgot, and all of a sudden they’re running up against a deadline. And with so many cutbacks and everything else going on on the Medicare and Social Security side, we need to take more responsibility, lead ourselves through the system and do our research.”
Ready to dig in? LIMRA’s 5-step guide to planning for healthcare costs in retirement is a great place to start . It will help you get organized, understand your options, and know what to ask your advisor about building a healthcare strategy before you retire.