Have you thought about your Medicare supplemental insurance yet?
Or even more challenging: will you have to help an elder work through their decisions?
How Medicare feels.
How will it affect your financial independence?
I learned a lot about Medicare Part B and Part D insurance policies while taking care of my father’s finances, and I learned even more this year when I signed up for my own Medicare.
You can guess what I’m going to help my spouse with next year.
(The good news is that this post includes a free PDF copy of a very useful book on your Medicare options. If nothing else, its free worksheet will confirm that you’re on track for the right plans at the right times.)
Who needs to know this Medicare stuff? Well, first, everyone needs to be aware of the financial parameters before the year in which you turn age 63. Maybe you already know how to spell IRMAA, and later in this post we’ll discuss ways to avoid that annual issue.
Then you need to plan for major shifts in your healthcare and prescription insurance, even if you’re still able to see the same doctors. Here’s some examples.
Military families use Medicare too.
If you’ll have a military pension then you’re eligible for Tricare For Life, which greatly simplifies the Medicare puzzle.
“Suitable for ages 65 and up.”
(That pension could be from active duty, or Chapter 61 disability, or a Reserve [non-regular] pension.) Once you’re enrolled in Medicare & TFL, your spouse is also eligible for TFL when they enroll in Medicare.
(Tricare For Life is still a bad reason to gut it out to 20 for a pension, and there are other financial solutions to this insurance challenge. We’ll discuss all of your options.)
If you’re a military veteran (but without a military pension) then you’ll want to use Medicare along with your VA benefits for your service-related conditions. It’s a patchwork of coverage that strongly depends on your local VA clinic (if you’re near one with good care) and your VA disability rating.
Even if you’re a vet with a 100% permanent+total VA disability rating (without a military pension)… you can hedge your bets by signing up for Medicare. If your VA benefits change later in your life, or your local VA clinic turns into a crowded mess, then Medicare can step into the gap– but that coordination works a lot better if you’ve signed up for Medicare when you’re supposed to.
Especially if you’re a vet living overseas (with or without a military pension), you still want to consider signing up for Medicare. If you ever return to the U.S. after age 65 and get sick or hurt, you could destroy your finances before you even leave the emergency room– unless you have Medicare.
Complicated? You bet. I get these questions Every. Week. These days I’m also getting them from adult children in military families who are pretty sure that Mom or Dad is eligible for some veterans benefits, but they don’t know where to start.
Disclaimers & disclosures
(The FTC wants you to know that this post contains an affiliate… phone number: 530-269-8083. All of the revenue credited to this affiliate number or its link is donated straight to Fisher House Foundation– I never even touch the money. If this post helps you choose your Medicare supplemental insurance, then you can also help build the next Fisher House.)
We’re going deep into this topic: 4400 words. You can find the short-form content everywhere else on the Internet, but here we’ll explain all of the jargon, unintended consequences, and outright conflicts. Don’t bet your financial & Medicare future on an Instagram reel.
Before we dig in: if you’re looking for a video summary, in the “Related articles” at the bottom of this post I’ll include three other YouTubers who’ve also signed up with affiliate phone numbers for their webinars. We all know each other and I trust their credibility. You can too.
Use a Medicare insurance broker!
This is the important part: like all insurance policies, eager brokers are standing by to help you navigate your Medicare choices.
You can work directly with an insurer’s broker (working for their insurance company), or you can use an independent broker (paid commissions by any of the insurance companies). This is all free to you, but you have to do your due diligence to avoid being steered into policies that pay higher commissions to a broker while being less than the best fit for your specific needs.
Spoiler: I know Chapter better than the other Medicare insurance brokers, and that phone number is my affiliate relationship. Chapter is the Easy Button, and I’ll mention a couple of other insurance brokers at the end of this post.
The Medicare brokerage business is serious money. In 2025, the Dept of Justice filed a False Claims Act complaint against Aetna, Humana, Anthem/Elevance, eHealth, GoHealth, CVS, and SelectQuote.
The complaint alleges that from 2016 through at least 2021, these insurers paid hundreds of millions of dollars in illegal kickbacks to these brokers in exchange for enrollments into Medicare Advantage plans.
Later in this post, we’ll get into why Medicare Advantage plans can mutate into toxic referrals. “Free” seems very attractive– until it stops working.
Quickstart Medicare
It’s that simple?
First, here’s the basic bare-minimum Medicare info:
– Medicare Part A is inpatient hospital insurance with no premiums, but there’s a deductible and more fees kick in after 60 days.
– Medicare Part B is outpatient hospital insurance plus preventive services, with a bunch of other miscellaneous coverage that’s not included in Part A.
– Part B has premiums & deductibles. Even worse, there are specific enrollment periods. If you don’t sign up for it at the right time, then you pay a lifetime penalty as a higher premium. This is especially risky if you’re a military veteran living overseas.
– Part B has a coinsurance cost of 20% of the Medicare-approved amount. Those italics are important, and I’ll explain those details below. Many people with Part B add Tricare For Life or other Medicare supplemental insurance to cover their coinsurance costs– but supplemental insurance is optional and you can go without it.
– Medicare Part C is private health insurance to cover Parts A&B, plus possibly other benefits. This is Medicare Advantage, and even when it’s “free” it still has pitfalls. We’ll cover those problems later, but brokers should steer families away from Medicare Advantage unless there’s a very good reason for a certain network.
– Medicare Part D is optional prescription insurance… but if you sign up later, you might pay a lifetime penalty as a higher premium.
Confused yet? Yeah.
Wait until you see the rest of the Medicare alphabet for the Part B supplemental insurance policies of Plans F through N. (Pro tip: As of the date of this post, Plan G is the most comprehensive and possibly the cheapest.) And then you’d consider Part D prescription insurance.
The good news is that if you can handle Tricare (especially Tricare Prime referrals) or the Affordable Care Act exchanges, then you can learn to handle Medicare. It’s a couple of big decisions up front followed by annual tweaks.
Sign up for Medicare Part A, Part B, and Part D when you’re supposed to.
If you’re financially independent and no longer receiving employer health insurance in your 60s, then you’re probably going to sign up for Medicare as soon as you’re eligible.
Your Initial Enrollment Period is generally [+/- three months] around the month you turn age 65, but there are edge cases.
In some situations (severe chronic conditions or disability) you might already have Medicare Part A before age 65. Talk with your doctor, or with a VA Veteran Service Officer, or with a Medicare insurance broker. This is frequently seen among vets with a 100% P&T VA disability rating, or anyone receiving Social Security Disability Insurance for over 24 months.
If you’re still working for an employer as you approach age 65, then starting Medicare gets more complicated. You can avoid penalties for late applications if you have the right group health insurance from your employer (or your spouse’s employer) of at least 20 employees.
Don’t depend on your employer’s HR manual, or your co-worker’s advice, or the VA, or any other scuttlebutt. If you do this wrong then you’ll pay a lifetime penalty. Check with a Medicare insurance broker. They know the rules, they can look up the laws, and they’ll give you references to take back to your employer.
If you’re self-employed, or an independent contractor, or on the Affordable Care Act exchanges, or on COBRA then sign up for Medicare as soon as you’re in the Initial Enrollment Period around age 65.
Even Part D prescription insurance has penalties if your employer’s prescription coverage isn’t considered creditable. Your employer (of “at least 20 employees!”) is supposed to have that creditable information in their HR files.
Veterans with complete prescription coverage from the VA can consider that creditable coverage for Medicare Part D. However if you develop a new condition that needs a prescription not covered by the VA then you’re going to have to seek Part D prescription insurance or pay out of pocket.
Frankly, I wouldn’t screw around with this situation. Your doctor and the VA are not the best sources of health insurance advice when you work past 65, and HR might not correctly verify that you have the right employer group health plan.
In 2017, over 700,000 people paid late enrollment penalties averaging 28% increases— for life.
Don’t be late.
If you intend to delay signing up for Medicare then browse a few insurance broker’s websites, and talk with Chapter at 530-269-8083. They’ve seen these employer pitfalls thousands of times and they’ll guide you through the right questions.
Avoid big financial moves during the year you turn age 63.
If your Modified Adjusted Gross Income is high enough (in 2025, $106K filing Single or $212K Married Filing Jointly) then two years later the first tier of Income-Related Monthly Adjustment Amounts adds another $74/month to your $185/month Medicare Part B premium… and yes, it kicks in two years later.
Each trigger of IRMAA lasts for a year. It’s calculated from your income-tax returns of two years earlier, hence the need to pay attention to this before the year in which you turn age 63.
For more info, search for the IRMAA keyword in my other Medicare post.
There are appeals for IRMAA, too, and they’re explained in excruciating detail at that post.
Here’s a humblebrag flex first-world problem that might apply to you too: my spouse and I are delaying Social Security to age 70 because as soon as we start it, our higher MAGI means we’ll pay IRMAA for life.
And because we’re not receiving Social Security yet, for the next five years we’ll pay our Medicare Part B premiums through monthly deductions from our checking accounts.
Stop contributing to your Health Savings Account
*Now* it’s time to use your HSA.
If you’re starting Medicare at age 65, then stop contributing to your HSA account a month before then.
If you’re working past age 65, then you’ll need to stop HSA contributions at least six months before you start Medicare Part A, or Part B, or your Social Security benefits.
Your Medicare benefits are backdated six months from leaving your employer’s health insurance, and you can’t contribute to a HSA when you’re on Medicare.
You know that the IRS has penalties for excess HSA contributions.
The good news is that you can pay your Medicare Part B and Part D premiums from your HSA (if you want). You can even pay your Medicare Advantage premiums (if that policy has premiums) from your HSA. However you can’t pay your Medigap premiums from your HSA because… Medigap premiums are not considered a qualified medical expense.
(I’m just reporting the HSA rules here. If you have more insight on this logic gap then please send me a reference.)
Why you might want to skip Medicare supplemental insurance:
I can see the comments now: “Heresy!”
Of course at least one of us military vets has wondered about the self-insurance math. Sometimes we can save a lot of premium payments by accepting the risk.
Yet consider John Greaney, who reached financial independence in 1994(!) at the age of 38(!!). He’s been on Medicare since early 2021 and he’s decided to skip a Medicare supplemental insurance policy (for now).
His compelling logic is that he’s relatively healthy (so far), and wealthy enough to self-insure for the risk of paying the 20% coinsurance fee that most people would cover with a Medigap policy.
Let the math sink in for a minute: it’s the 20% coinsurance of the Medicare-approved rate that the medical service accepts, not 20% of the retail price on the Explanation Of Benefits. You still have an annual deductible to pay for Part B, but 20% of the Medicare-approved reimbursement rate is less than “20% of the hospital bill.”
If your doctor sells you a $25,000 total knee replacement and Medicare’s approved amount is only $9654, then your 20% share is not $5000. Medicare only reimburses the doctor & facility a total of $7723, and your part is 20% of $9654 ( = $1930). There’s still the deductible, and there might be other procedures (and fees) but you’re eligible for an estimate before the cutting starts. Shop around.
It’s possible that Medigap insurance costs more in premiums than the coinsurance that it covers– especially if you’re relatively healthy.
Caution— if you’re:
- in poor health or with pre-existing conditions, or
- likely to age badly (family history), or
- likely to face insurance underwriting, or
- concerned that this idea keeps you (or your spouse) awake at night, then buy a Medigap policy.
Buy the Medicare Part B supplemental insurance policy for peace of mind. It’s a lot easier to buy these policies at age 65 when you’re in good health and will face minimal underwriting.
But if you’re still healthy & active in your 60s, then maybe you want to self-insure for that coinsurance. This is especially compelling if you can get VA healthcare or if you’re living overseas and a Medigap policy wouldn’t cover you anyway.
Just be aware that when you go outside of the Medigap guaranteed issue period (generally six months after you sign up for Part B) then you’re possibly vulnerable to underwriting.
And of course if you’re eligible for Tricare For Life then that’s your Medicare supplemental insurance. TFL is currently free of enrollment and coinsurance fees when you’re covered by Medicare Part A&B.
If you’re tempted to save on Medigap premiums by buying “free” Medicare Advantage, well, keep reading.
“Thanks so much Nords, that’s thoroughly confusing. Now what?!?”
TL;DR: call Chapter at 530-269-8083, my affiliate phone number. (Have I mentioned it’s free?)
Fill out the worksheet in the free book (PDF) attached to this post, “It’s Not That Complicated” or use this (affiliate) link to go through the screening questions on Chapter’s site.
Why Chapter?
Chapter is an independent insurance broker. The startup was founded in 2020, and in 2024-25 they’ve scored VC rounds of $50M and $75M. Although some of the co-founders and VC execs have moved on, the company was recently valued at $1.5B. In my angel-investing experience, this is a big deal. They’re growing fast and earning revenue.
Of course this is also the stage where startups start spewing affiliate commissions with that righteous cash (like PersonalCapital or Amazon), which ideally spurs even more growth & revenue.
In early 2025 I started noticing Chapter in the blog posts & videos of financial people I follow (I’ve linked them at the end of this post) and in August I was invited to a sponsor dinner at FinCon.
Chapter’s team treated a handful of us FinCon attendees to a very nice Portland City Grill dinner (I had the braised shortribs) and then their team endured two hours of interrogation. (Well, at least from me and Rob Berger. We can both get a little… intense.) My first question was “Why me?”, and Chapter’s answer was “your military audience.”
Fair enough. Zach & Kevin know me a lot better now.
The team pointed out that many Silicon Valley startups were created by tech co-founders who had a bad personal experience with food delivery, a taxi ride, or a car rental. However Chapter was started by a tech team whose parents had a bad experience with Medicare supplemental insurance. They’re one of the few brokers to grow out of tech instead of out of the traditional insurance industry.
Chapter has collected the nation’s publicly-available Medicare supplemental & prescription insurance information into a database with tens of thousands of policies across dozens of insurers. (Building it took a couple of years of money from angel investors. Today, maintaining the Medigap & Medicare Advantage data is a full-time job.) Chapter is the only national Medicare advisor that compares every available plan, so you can be sure you’re seeing all your options– not just a select few.
Next they’ve negotiated contracts with most of those insurers.
If you decide to buy a policy from an insurer referred by Chapter, and if Chapter happens to have a contract with that insurer, then Chapter gets paid by the insurer. (And if you use my affiliate phone number to have that conversation, then a small slice of that money goes to Fisher House Foundation.) Of course you decide to buy a policy from an insurer where Chapter doesn’t have a contract (not yet!) then… Chapter doesn’t get paid.
Here’s the interesting part: the Chapter sales team is paid a salary (with a bonus plan) instead of working on commission. They run the database and use your answers to find a bunch of policies that could work for you, but the call center doesn’t know which insurers will pay Chapter.
You’ll be told all of your Medicare options– not just the few that pay higher commissions.
Medicare D insurers generally don’t pay commissions to brokers (not yet anyway), yet Chapter still has the policy data and will share their recommendations based on your medications. They know that you’re going to tweak this particular policy every year or two, and maybe buy other policies along the way.
Why should we call Chapter instead of running our own database search? Well, they’ve learned (the hard way) that we clients don’t understand the vocabulary or the policies well enough to make an unassisted decision. (Blame it on my fellow Baby Boomers. Good luck, GenX.) Chapter asks the right questions and then verifies that the candidate policies have the features we need & want. It’s up to you to decide if you want to buy one.
Chapter also has an advocacy team who will handle corrections and appeals for you by talking directly with your insurer or by helping you fill out the paperwork.
If you insist on using a website before you call, you can browse Chapter’s website with my affiliate link.
The site asked me eight questions and then offered to text their list of plans or call me. I chose a text, and a few seconds later they texted that they’ll call me to finish comparing the plans. I replied “STOP” and they promised to unsubscribe me.
You know that I tested my own affiliate phone number to call Chapter. (530-269-8083 goes to Auburn CA.) The call center representative made all of the right disclosures and asked all of the right questions. When I eventually mentioned the VA (and later Tricare For Life) he reviewed how they all work together. He suggested that I didn’t need any Medicare supplemental insurance or Part D insurance, yet he still offered to dig into the details of my one prescription for a low-dose statin.
There was no upsell and he made all of the right recommendations. The call was answered immediately, there was no hold time, and we were finished in under 10 minutes.
If you decide to contact Chapter, please leave a comment on how the conversation goes for you.
Medicare’s Annual Enrollment Period starts 15 October, and by then the call center’s very busy researching quotes for both Medigap and Part D prescription insurance. Many of my fellow Boomers will use the AEP to shop their current plans against the competition, and they might save money.
Other Boomers are calling in a panic because their current insurer has been indicted canceled their plan and they need to find a new insurer.
Chapter can’t guarantee that they’ll save you money, but up through 2024 they’ve saved callers an average of $1100/year. Read Chapter’s reviews. The typical phone call takes 20 minutes. Do the math.
Some of you already know that insurance companies are going to mercilessly market their policies through TV ads, mailers, phone calls, and junk texts. (They’ll even rent a kiosk at Wal-Mart and sign you up on the spot.) I started getting the pitches months before age 65.
Medicare Part C (Medicare Advantage)
Briefly: don’t do this unless you know exactly what you’re buying.
If you think you know what you’re doing, you’re probably still wrong. Check with Chapter (530-269-8083) or contact me.
“Free” looks pretty good, and a few insurers will even “give back” your Medicare Part B premium or offer additional benefits like free gym memberships or dental care.
SHIP: avoid Medicare Advantage.
Beware, military families: Medicare Advantage makes Tricare Prime referrals look simple. Way too many MA insurers have taken a line from the VA’s old playbook: “Lie & Deny Until They Die.”
John Greaney has already broken down the numbers of an insurer’s incentives for Medicare Advantage in this 2022 post, and in the last few years the trend is even worse.
Medicare Advantage is all rainbows & unicorns until your health declines with age (and maybe a little of your stamina & cognition too). Then the typical elder ends up in an endless loop of referrals, authorizations, restrictions, and additional payments. (Ask the adult children of those elders how they know this.) Many seniors simply give up in frustration and pay out of their own pockets when they could have had a better Medigap policy.
My fellow mentors on the Millionaire Money Mentors forum are not price-sensitive about insurance, yet even they complain about the bureaucratic hoops that their Medicare Advantage elders have to jump through. Moms & Dads of the MMMs were really bragging happy with MA at age 65– but now that they’re in their 80s and have additional health issues, suddenly the plan stops working.
Here’s the catch: when you first enroll in Medicare Part B, your Medigap Open Enrollment Period allows you to enroll in any Medicare supplemental insurance policy without underwriting.
Six months later, though, from then on you could be subject to underwriting or other special enrollment rules. There are lots of exceptions to the rules, and you might be able to avoid underwriting, but you’re on the mercy of state laws or other insurer rules.
At our FinCon dinner, the Chapter team said that their employees are not only unable to see which insurance policies pay commissions to Chapter– they’re not even allowed to sign you up for Medicare Advantage. They have to get approval from their supervisors before everyone concludes that it’s the right policy.
Want to read more? Here’s the free book “It’s Not That Complicated: The Three Medicare Decisions to Protect Your Health and Money.”
(As you may have noticed by now, the title sentence “It’s Not That Complicated” is snarcasm.)
I happened to buy it on Amazon months before Chapter offered to share it with our audiences, and it’s a very good read. You can also watch Ari on webinars & podcasts with other personal-finance content creators– see the “Related articles” links below.
Call To Action
Check the related links, and then call (literally!) Chapter at 530-269-8083 for more advice.
But first, a corporate lawyer’s final disclosure.
Here’s an additional disclaimer if you decide to call Chapter at 530-269-8083:
“Memoir, Inc. d/b/a Chapter is a privately-owned, data and technology-enabled advisory that helps older Americans navigate retirement. Insurance agency services are provided by Chapter Advisory, LLC, a licensed health insurance agency and wholly owned subsidiary of Memoir, Inc. In California, Chapter Advisory, LLC does business as Chapter Insurance Services (Lic. No. 6003691).
The information on this site has been developed for general informational and educational purposes.
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.”
“Average potential savings are based on realized premium, co-pay, and out of pocket savings estimates self-reported by consumers that worked with Chapter Advisory LLC to enroll in a Medicare Supplement, Medicare Advantage, and/or Part D Prescription Drug Plan. The average is limited to consumers that chose to self-report. Savings information is subject to periodic updates and corrections. There is no guarantee of savings and any savings may vary by policy type, state, or other factors.”
There’s an affiliate link in this post, and it supports a military-friendly charity. Try your military base library or local public library before you pay money for these books– in any format.
Military Financial Independence on Amazon:
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Raising Your Money-Savvy Family on Amazon:
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Related articles:
Azul Wells video: “Exposing The Truth About Medicare” with Chapter co-founder Ari Parker
Fritz Gilbert’s Medicare 101 webinar and seven crucial Medicare mistakes with Chapter co-founder Ari Parker
Rob Berger’s live Medicare Q&A with Chapter co-founder Ari Parker
(A two-hour marathon! With chapters and a transcript.
IRMAA appeals are reviewed at 1:58:30… and after 1:34:30, there’s some football trash talk.)
Boomer Benefits
The Boomer Benefits Facebook group
(850K followers with thousands of questions answered every year.)
It’s Not That Complicated: Ari Parker Medicare Chapter book
(“The Three Medicare Decisions to Protect Your Health and Money.”)
The “expense ratio” of Medicare Advantage plans
(This drives home the pricing of MA plans and how you’re exploited later.)
Medicare, Tricare For Life, And Your Expiring Military ID Card
Military Financial Independence 