Did you know there are over 24,000 Medicare plans? How in the world is somebody supposed to know which one is best for them?
And even once you choose the plan you think is best, those plans change every year. How do you keep up?
Careblazer, when I started researching Medicare, I quickly became overwhelmed and confused. So I sat down with Ari Parker, one of the co-founders of Chapter, a company that helps seniors choose the Medicare plan that fits them best. I asked him what costly mistakes seniors should avoid, and what to be cautious about when working with Medicare brokerage companies.
Here are the mistakes Ari sees most, and how to avoid them.
What Is Medicare?
Medicare is health insurance for people 65 and older. It’s also health insurance for people under 65 who have received disability benefits for 24 months or more, and for some younger people with end-stage renal disease or ALS.
Ari broke down the two terms people hear most:
- Part A is your hospital insurance. If you’re wearing a hospital wristband, that’s Part A.
- Part B is your outpatient insurance. It’s for everything outside the hospital.
Together, Part A and Part B are called Original Medicare.
Mistake 1: Having Only Original Medicare
The biggest mistake Ari sees is people who have only Original Medicare.
It’s one of the biggest misconceptions out there. Because Original Medicare comes from the government, people think it covers all their costs. It doesn’t. It still leaves you responsible for at least 20% of your medical costs out of pocket, and there’s no cap on that 20%.
Ari’s mom lives in the Chicago area. She needed a knee replacement, a $50,000 procedure. Without some kind of additional coverage, she would have owed $10,000 for that knee.
To get comprehensive coverage, you have two options:
- A Medicare Supplement plan, which is the most comprehensive and flexible type of coverage. If you go this route, you’d add a standalone prescription drug plan.
- A Medicare Advantage plan, which replaces Original Medicare and is run by a private insurance company. These are the plans you see advertised everywhere in the fall.
The options vary county by county across the United States, so work with someone who can sort through all of your options wherever you live.
Mistake 2: Not Reviewing Your Medicare Plan Every Year
Many, many seniors never review their coverage. That’s a shame, because your plan can change for next year.
That’s why you see so many Medicare commercials in the fall. The annual enrollment period runs from October 15 to December 7, and it’s when people on Medicare can make changes for the upcoming year.
Before it starts, you’ll get something in the mail called the annual notice of change. It describes how your plan will work next year. So yes, your plan can change what it covers without you really noticing.
The rules change too. For example, there’s now a maximum out-of-pocket cap on your prescription costs: $2,100 for 2026. But to take advantage of it, each of your prescriptions has to be covered under the plan you choose for next year.
Review your three Ps
Take that annual notice of change and go through what Chapter calls your three Ps:
- Providers. Which doctors do you want to see? Which doctors would you want to see if your health changed?
- Prescriptions. What medications do you take? Brand name or generic? Which pharmacy do you like, a national chain or a mom and pop drug store?
- Priorities. Write out what matters most to you for the upcoming year.
Then schedule a consultation with an independent, unbiased Medicare advisor to evaluate all your options, or go to Medicare.gov.
Mistake 3: Not Signing Up for Medicare on Time
If you don’t sign up for Medicare on time, you can face late enrollment penalties.
Medicare is generally designed to be your primary insurance, unless you or your spouse work for a large employer. Ari calls this the rule of 20: an employer with 20 or more employees. So know your Medicare enrollment deadlines.
Another misconception is that applying for Medicare takes forever. It actually takes less than 10 minutes if you do it through your online Social Security account. It’s fast, safe and secure.
Mistake 4: Working With Someone Who Only Shows You a Few Plans
If you’re responding to an unsolicited phone call, a spam text message or a direct mailer, you’re probably working with someone who is captive to one insurance company, or maybe two or three. And they’re only showing you those few options.
Why would a company only show you a handful of plans? Because those are the plans that pay them. Ari called it a broken industry: there’s no duty to act in the person’s best interest. That has led to worse health outcomes, and to huge costs when people realize their doctor is out of network and they owe 100% at the time of service.
Even well-intentioned people are limited by their tools. Medicare.gov, for example, doesn’t let you enter your doctors for certain plans to see whether they accept that insurance.
It can go further than that. In May 2025, the Department of Justice filed a lawsuit against three national health insurers and three large Medicare brokerages. It alleges the insurers paid the brokers kickbacks to steer seniors into their plans, and that some brokers steered people with disabilities away from certain plans, even when those plans might have been the best fit. These are allegations, and no court has ruled on them. But when I heard about it, I thought, that’s horrible.
Red flags to watch for
- An unsolicited phone call.
- A spam text message or a direct mailer.
- Anyone asking for your personal information when you didn’t contact them first or give permission to be contacted.
Make sure it’s someone you trust. I go through more ways to protect your loved one from calls like these in how to protect your loved one with dementia from scams.
Where to Get Unbiased Medicare Help
There’s no charge to work with a Medicare advisor. Make sure the person you work with is independent and unbiased, or go to Medicare.gov.
Chapter is a company I have a lot of respect for. What makes it different is that the advisors helping you choose a plan are blinded to what each insurance company pays. They have no incentive to show you the plans that make the company the most money, and no incentive to hide the ones that don’t, because they don’t know which is which. Ari says Chapter’s advisors have every plan at their fingertips.
Here’s how it works:
- You talk to a real person, a licensed Medicare advisor who knows the rules for your state.
- You have a one-on-one conversation of 45 minutes or longer about your providers, your prescriptions and your priorities.
- They give you a short list of plans that fit, and help you apply for the one you choose.
- They handle the paperwork and support you all year. If you lose your ID card, they’ll help you get another one. If a claim from the doctor confuses you, they’ll help you decipher it. If your copay at the pharmacy seems outrageous, they’ll find out why.
- There’s no cost to you.
If you have a Medicare question, whether you want to know if you’re on the right plan or need help applying, visit askchapter.org/careblazers or call Chapter at 504-490-0080 for free, personalized guidance to make sure you’re on the right plan this year. This video is sponsored by Chapter, a company I personally respect and trust.
Chapter: Chapter and its affiliates are not connected with or endorsed by any government entity or the federal Medicare program. Chapter Advisory, LLC represents Medicare Advantage HMO, PPO, and PFFS organizations and stand alone prescription drug plans that have a Medicare contract. Enrollment depends on the plan’s contract renewal. While we have a database of every Medicare plan nationwide and can help you to search among all plans, we have contracts with many but not all plans. As a result, we do not offer every plan available in your area. Currently we represent 50 organizations which offer 18,160 products nationwide. We search and recommend all plans, even those we don’t directly offer. You can contact a licensed Chapter agent to find out the number of products available in your specific area. Please contact Medicare.gov, 1-800-Medicare, or your local State Health Insurance Program (SHIP) to get information on all of your options.
What If It Isn’t Open Enrollment?
You may be reading this in the middle of the year. Whether you can do anything now depends on your circumstances. If you recently moved, for example, that creates a special election period to choose different coverage.
Ari named three groups who should start looking now:
- You’re turning 65 soon. Now is the time to get your Medicare set up.
- You’re past 65 and still working for a large employer, or your spouse is (the rule of 20 again). If you’re retiring before the end of the year, set up your coverage now so there’s no gap at the start of next year.
- You’re already on Medicare. Chapter can discuss next year’s plan options from October 1, and changes are submitted from October 15 to December 7.
Medicare is a lot of information to digest. If you’re on it, just make sure you review your coverage during the annual enrollment period every year.
When you’re managing a loved one’s insurance on top of everything else, it’s a lot to sort out alone. Inside the Care Collective, Careblazers bring questions like these to our weekly support rooms and work through the practical side of caregiving together, alongside how to take care of yourself while you do it. You can learn more here.
Sources & References
Medicare.gov, Get started with Medicare
