Your Medicare Choice Might Be Permanent – Here’s What to Know (with Medicare Specialist Andrew Mersereau)

When it comes to your Medicare choice, the decisions you make at age 65 (or even slightly before) can have long-lasting consequences. Yet many end up choosing a plan based on general advice, slick marketing, or a brief conversation with their benefits department.

To help cut through the confusion, we sat down with Andrew Mersereau, a Medicare specialist with over 24 years of experience guiding individuals through enrollment, plan selection, and strategy. Andrew is known for his no-nonsense, education-first approach to Medicare and has helped countless clients avoid costly mistakes.

Today we’re breaking down everything you need to know to make a confident, well-informed Medicare choice that fits your needs, especially if you’re financially secure, still working at 65, or considering a Roth conversion or property sale that could spike your income.

Let’s dive in.

Listen Now:  iTunes |  Spotify | iHeartRadio | Amazon Music

What Is Medicare, Really?

Before diving into strategies, it’s helpful to revisit the basics. Medicare is a federal health insurance program for people 65 and older, as well as some younger individuals with disabilities. But “Medicare” isn’t one plan, it’s a collection of parts:

  • Part A: Hospital coverage (inpatient)

  • Part B: Medical coverage (outpatient care, doctor visits, preventive services)

  • Part C: Medicare Advantage plans offered by private insurers as an alternative to A and B

  • Part D: Prescription drug coverage

Original Medicare (Parts A and B) is provided by the federal government. To cover additional costs and services, many people add Part D and either a Supplement (Medigap) policy or an Advantage plan.

The Big Decision: Supplement vs. Advantage

This is the crossroads most people face, and it’s not as straightforward as it seems.

Medicare Advantage (Part C)

Medicare Advantage plans are offered by private insurance companies and typically include Parts A, B, and D bundled together. These plans often tout extra perks like dental, vision, gym memberships, or transportation to doctor visits.

But those extras come with trade-offs. Advantage plans often:

  • Have narrow provider networks

  • Require referrals for specialists

  • Use prior authorizations for many procedures

  • Limit care to a specific geographic region

These plans are appealing due to their low or zero-dollar premiums, but you may find yourself paying more out of pocket when you actually need care.

Medicare Supplement (Medigap)

Medigap policies work alongside Original Medicare to pay for out-of-pocket costs like coinsurance, copayments, and deductibles. They do not include drug coverage, so you’d add a standalone Part D plan.

Key benefits of Medigap plans:

  • See any provider in the U.S. who accepts Medicare—no referrals needed

  • No network restrictions

  • Predictable costs with limited out-of-pocket expenses

For frequent travelers, snowbirds, or anyone who wants maximum freedom in choosing providers, Medigap is often the better long-term choice.

“People often pick Advantage for the low monthly price, but later regret the restrictions,” Andrew warns. “Your Supplement choice may cost more monthly, but it gives you far greater control.”

Why Your First Medicare Choice Might Be Permanent

Here’s the part most people don’t realize: the choice you make when you first sign up, especially between Supplement and Advantage, can be extremely hard to reverse.

Under federal law, you’re guaranteed acceptance into any Medigap plan only during your initial enrollment period (usually the six months after you enroll in Medicare Part B). After that window closes:

  • Insurance companies can ask health questions

  • They can deny you based on preexisting conditions

  • Approval becomes much more difficult as you age or develop medical issues

Andrew says it plainly:

“In my experience, 80% of people who try to switch from Advantage to Supplement later are denied.”

This is why the decision you make when you first sign up is so critical. Switching may not be an option later.

IRMAA and Income Traps: What Affluent Retirees Need to Know

Medicare premiums aren’t fixed for everyone. If your income is high, you may be subject to the IRMAA (Income-Related Monthly Adjustment Amount). This surcharge applies to Parts B and D and is based on your Modified Adjusted Gross Income (MAGI) from two years prior.

Here’s what can trigger IRMAA:

  • Roth conversions

  • Selling a business or property

  • Large capital gains

  • Taking large IRA distributions

A Common Scenario:

Janet, 64, sells her investment property and earns a $300,000 gain. Two years later, she’s shocked to find her Medicare premiums more than double, she’s now in an IRMAA tier that costs her over $500 more per month.

These are avoidable surprises, but only with proper planning.

Still Working at 65? Don’t Assume You Can Delay Medicare

Many people working past 65 wonder if they can delay Medicare enrollment. The answer: only if you have credible employer coverage.

Your plan must:

  • Cover 20 or more employees

  • Be deemed creditable by Medicare

  • Meet specific drug coverage standards

If it doesn’t, and you delay enrolling, you may face lifetime penalties based on your Medicare choice.

Mersereau’s advice: always confirm with HR in writing that your coverage meets Medicare’s standards, and compare your total healthcare costs before making a decision.

Important: If you’re still contributing to a Health Savings Account (HSA), enrolling in any part of Medicare makes you ineligible to keep contributing.

Medicare Doesn’t Cover Everything. Here’s What’s Missing:

Even the best Medicare plans don’t cover everything. Here are the biggest gaps that surprise people:

  • Hearing aids

  • Routine dental care

  • Eyeglasses and eye exams

  • Long-term care (like assisted living)

  • Home modifications or private-duty nursing

  • Unlimited rehabilitation or therapy

You may need private insurance, Medicaid, or a long-term care policy to bridge these gaps. Supplement plans won’t help with most of these either, they’re for traditional medical expenses only.

For Snowbirds and Travelers: Choose Wisely

If you live part of the year in Florida and the rest in Colorado, or travel often, your plan choice is especially important.

Advantage plans are often limited to regional networks, so out-of-state care may not be covered. Supplement plans allow access to any Medicare provider in the country, making them ideal for travelers or dual-state living.

Timeline: What to Do at 63, 64, and 65

Turning 65 is a major milestone, not just for birthdays, but for healthcare decisions that can impact your financial future. To help you stay ahead of deadlines and avoid costly missteps, here’s a step-by-step timeline of what to focus on at ages 63, 64, and in the months leading up to your Medicare choice and enrollment.

Age 63:

  • Begin tracking your income to anticipate IRMAA brackets

  • Evaluate if Roth conversions, property sales, or business exits are better done now

  • Schedule a financial planning session to model different Medicare scenarios

Age 64:

  • Research Medicare basics using Medicare.gov

  • Make a list of your doctors and medications to compare plan compatibility

  • Talk to a Medicare specialist or broker, ideally one who is fee-transparent and non-commission focused

3-6 Months Before Turning 65:

  • Enroll in Medicare Parts A and B via Social Security

  • Choose either a Supplement and Part D or an Advantage plan

  • Get proof of credible coverage from your employer if you’re deferring enrollment

Red Flags to Watch For

  • Too-good-to-be-true Advantage ads
    “Free this” and “zero-dollar that” often hide tight restrictions and surprise bills.

  • Advice from friends
    Everyone’s situation is different. What works for one person could be a disaster for another.

  • Brokers pushing one plan type
    A good broker will help you compare, not sell you the highest-commission product.

  • Skipping Part D because you take no meds
    This can result in penalties later. It’s often smarter to enroll in the lowest-cost plan anyway.

FAQ: Quick Medicare Questions Answered

Q: Is it ever smart to go with just A and B?
A: Rarely. Without a Supplement or Advantage plan, your out-of-pocket costs are unlimited.

Q: Can I change my mind later?
A: With drug plans (Part D), yes. With Supplement plans, possibly, but you may be denied.

Q: What if I have a concierge doctor?
A: You can keep them, but you’ll still need A and B, plus coverage for hospitals, specialists, and serious illnesses.

Q: Does my state affect my ability to switch plans?
A: Yes. Some states have more lenient rules, but most follow the six-month initial enrollment protection rule.

Final Thoughts: The Smartest Move is an Educated One

Andrew Mersereau emphasizes that education, not advertising, should guide your Medicare choice.

“Don’t just follow an ad or assume what worked for a friend will work for you. Take the time to understand what you’re buying and why.”

And remember, using a Medicare broker doesn’t cost you extra. Rates are set by law, and a good broker can help you avoid expensive mistakes.

Whether you’re helping a parent, preparing for your own retirement, or simply curious about your options, the takeaway is clear: Medicare isn’t something to wing. It’s a decision that affects your access to care, your costs, and your peace of mind for years to come.

Need help navigating Medicare?

You can contact Andrew’s team at 719-955-4991. They offer education-driven guidance with no pressure.

6 important things to do when turning 65 – A Retirement Checklist 

Turning 65 – A Retirement Checklist

 

Are your turning 65 soon? Turning 65 is a major milestone and pivotal age for your retirement planning. Not only is this an important age for government programs like Medicare and Social Security, but it’s also a perfect time to check other parts of your financial plan, particularly if you’re about to retire. Here are 6 important things to do as you get closer to your 65th birthday to make sure this year and the many years that follow are amazing!  (P.S. Read to the end for a special bonus gift for turning 65!!)

 

  1. Prepare for Medicare
  2. Consider Long Term Care Insurance
  3. Review your Social Security Benefits
  4. Review Retirement Accounts
  5. Update Estate Planning Documents
  6. Get Tax Breaks

 


1. Prepare for Medicare

 

Medicare is the most common form of health care coverage for older Americans. The program has been in existence since 1965 and provides a way for seniors to have their health needs taken care of after they retire from the workforce.

 

What is Medicare?

 

Medicare is basically the federal government’s health insurance program for people 65 or older (or younger with disabilities). Medicare is primarily funded by payroll taxes paid by most employees, employers, and people who are self-employed. Funds are paid through the Hospital Insurance Trust Fund held by the U.S. Treasury.

 

When can I enroll in Medicare?

 

Starting 3 months before the month you turn 65, you are eligible to enroll in Medicare, you can also sign up during your birthday month and the three months following your 65th birthday. Essentially, you have a seven-month window to sign up for Medicare. Be mindful of your timing and enrollment because Medicare charges several late-enrollment penalties.

 

What does Medicare cover?

 

Medicare benefits vary depending on the enrollment plan you choose. Medicare is made up of four enrollment plans:  Medicare Part A, Part B, Part C, and Part D.

 

Here is a quick breakdown of the four parts of Medicare:

 

Medicare Part A: Know as the Original Medicare, Part A covers inpatient hospital care, home health, nursing, and hospice care. Part A is typically paired with Medicare Part B.

Medicare Part B: Still considered part of the Original Medicare, Part B helps cover doctor’s visits, lab work, diagnostic and preventative care, and mental health. It does not include dental and vision benefits.

Medicare Part C: This option offers traditional Medicare coverage but includes more coverage for routine healthcare that you use every day, routine dental care, vision care, and hearing. Plus, it covers wellness programs and fitness memberships. Medicare Part C is also known as Medicare Advantage and is a form of private insurance. Note that you will not be automatically enrolled in these benefits.

Medicare Part D: Medicare Part D is a stand-alone plan provided through private insurers that covers the costs of prescription drugs.  Most people will need Medicare Part D prescription drug coverage. Even if you’re fortunate enough to be in good health now, you may need significant prescription drugs in the future.

Age 65 Medicare

 

While Medicare is great it’s not going to cover all your medical expenses. You’ll still be responsible for co-payments and deductibles just like on your employer’s health plan, and they can add up quickly.

To offset these expenses, a Medicare Supplement (Medigap) insurance policy could be a good option as well. Medigap is offered by private insurance companies and covers such as co-payments, deductibles, and health care if you travel outside the U.S.

 

How can I enroll in Medicare?

 

For most people, applying for Medicare is a straightforward process. If you already receive retirement benefits from Social Security or the Railroad Retirement Board, you’ll be signed up automatically for Part A and Part B.

If you aren’t receiving retirement benefits, and you don’t have health coverage through an employer or spouse’s employer, you will need to apply for Medicare during your 7-month enrollment window.

You can sign up for Medicare online, by phone, or in-person at a Social Security office.

Please note that if you have a Health Savings Account (HSA) or health insurance based on current employment, you may want to ask your HR office or insurance company how signing up for Medicare will affect you.

 

2. Consider Long Term Care Insurance

 

Another prudent thing to do when you are turning 65 is to consider your long-term care insurance options before retirement.

 

What is long-term care insurance?

 

The goal of long-term care is to help you maintain your daily life as you age. It helps to provide care if you are unable to perform daily activities on your own. It can include care in your home, nursing home, or assisted living facility.  The need for long-term care may result from unforeseen illnesses, accidents, and other chronic conditions associated with aging.

Medicare often does not provide long-term care coverage, so it is a good idea to factor this additional coverage in.

 

Why do I need long-term care insurance?

 

While it may be hard to imagine needing long-term care now, the U.S. Department of Health and Human Services estimates that someone turning age 65 today has almost a 70% chance of needing some type of long-term care service in their lifetime.

Unfortunately, long-term care coverage is often hindsight, only thinking about it once it is needed. Planning for it now can help you access better quality care quickly when you need it and help you and your family avoid costly claims.

 

How do I get long-term care insurance?

 

First, talk with a CERTIFIED FINANCIAL PLANNER™ about whether long-term care insurance makes sense for you. Coverage can be complex and expensive. A good Financial Advisor can help guide you to a plan that is right for you.

Most people buy their long-term care insurance through a financial advisor, however, some states offer State Partnership Programs and more employers are offering long-term care as a voluntary benefit.

It is important to start shopping before you would need coverage. While you can’t predict the future, if you wait until you are well into retirement and already having medical issues, you may be turned down or the premiums may be too high to make it a feasible option.

 

3. Review your Social Security Benefits

 

If you haven’t yet started to collect Social Security, your 65th birthday is a great time to review your social security strategy to help you maximize your benefits.

 

Age 65 Social Security

 

When can I take Social Security?

 

The Social Security Administration (SSA) considers the full retirement age is 66 if you were born from 1943 to 1954. The full retirement age increases gradually if you were born from 1955 to 1960 until it reaches 67. For anyone born in 1960 or later, full retirement benefits are payable at age 67.

In deciding when to start receiving Social Security retirement benefits, you need to consider your personal situation.

 

How can I maximize my Social Security Benefit?

 

Turning 65 might raise questions about how to maximize your Social Security befits in retirement. Rightfully so. Receiving benefits early can reduce your payments, however, the flip side is also true. If you’re still working or have savings that will allow you to wait a while on receiving benefits, your eventual payments will be higher. Your benefits can stand to grow 8% a year if you delay until age 70. Plus, cost of living adjustments (COLA) will also be included in that increase.

In addition to delaying receiving your benefits, it is important to make sure all your years of work have been counted. SSA calculates your benefits based on the 35 years in which you earn the most. If you haven’t clocked in 35 years, or the SSA doesn’t have those years recorded, it could hurt you.

Be sure to create a “My Social Security” account and check to make sure your work history is accurately depicted. It is wise to download and check your social security statement annually and update personal information as needed.

Another potential boost in your benefit can come from claiming spousal payments.  If you were married for at least 10 years, you can claim Social Security benefits based on an ex-spouse’s work record.

Everyone’s financial situation is different, but it can be helpful to have a plan for how you’re going to approach Social Security before you turn 65.

 

4. Review Retirement Accounts

 

Even if you are not planning to retire soon, now (and every quarter for that matter) is a good time to check in on your retirement accounts. Is your portfolio allocated in a way that lines up with your target retirement date? When is the last time you met with your financial advisor? Do you need to catch up a little?  Do you have a plan for your Required Minimum Distributions?

Meeting with a CERTIFIED FINANCIAL PLANNER™ can help you evaluate your risk tolerance in comparison to your retirement goals, make sure your investments are aligned to help you retire when you want, and make a plan for you to maintain the lifestyle you want in retirement.

A financial advisor can also help with planning for 401(k) catch-up contributions, RMDs, early withdrawals, or completing a Backdoor Roth.

A big hurdle as retirement approaches is often all the homework you have to do. Penalties, enrollments, coverage gaps, deadlines, etc. A great financial advisor can help guide you through this process.

If you are wondering how to find a great financial advisor, we have put a simple guide here. Or, we would love for you to schedule an appointment now to meet with one of our CERTIFIED FINANCIAL PLANNERs™.

 

5. Update Estate Planning Documents

 

The next item on the retirement checklist of important things to do when Turning 65 is to get your estate planning documents and legal ducks in a row. If you do not yet have an estate plan, will, medical directive, or financial power of attorney, it is time to get those in order. It is not too late! If you do have them, take some time to update them.

Have you had recent changes in personal circumstances? Do you need to update beneficiaries? Reviewing your plan at regular intervals, in addition to major life events, will help ensure that your assets and legacy are passed on in accordance with your wishes and that your beneficiaries receive their benefits as smoothly as possible.

Further, it is also a good idea to take inventory and organize all your financial documents. Keep a list of all your accounts (banking and investment), insurance, and estate documents as well as key contact information in a safe place. Make note of any safety deposit boxes you have. Keeping all this info organized and in one place will be a big help to your loved ones during a difficult time.

You’ll feel great knowing that you and your family are prepared

 

6. Get Tax Breaks

 

Finally, don’t let Medicare be the only gift to you when you turn 65. Starting in the year you turn 65, you qualify for a larger standard deduction when you file your federal income tax return. You may also qualify for extra state or local tax breaks at age 65.

Many states also offer senior property tax exemptions as well. For example, in Colorado for those who qualify, 50 percent of the first $200,000 of the actual value of the applicant’s primary residence is exempted. Check with your local tax assessor to see what property tax breaks may be available to you.

 

Turning 65 Birthday Advice

 

Relax and enjoy it. As much as turning 65 is a time to plan for retirement, it is also a time to celebrate.

If you plan to indulge in a much-deserved tropical getaway or a quick trip to visit your grandchildren, you may be able to take advantage of new travel discounts. Delta, American, and United Airlines all offer senior discounts on selected flights. Additionally, many hotels, car rental companies, and cruise lines all also offer senior discounts. So treat yourself!

Happy 65th! Cheers to many more!

Bonus Gift

FREE Social Security and Medicare

Cheat Sheet – Updated Annually 

Want this all simplified? Grab your Free Social Security and Medicare Info Guide and Cheat Sheet

Social Security & Medicare Cheat Sheet Post

Have more questions? We’d love to talk. You can reach us directly at 719-394-3900 or you can schedule a call here!

Thank You For Your Subscription

You’re in! Thanks for subscribing to our monthly newsletter. We will be sending you market updates, financial insights and inspiring travel ideas soon but in the meantime check out our blog, join us on Instagram or pop over to Pinterest.

Your Appointment Request has been Received

Thank you for reaching out! We are excited to learn more about you. Someone from our team will be in touch shortly.

Sign up now

Join us around the fire for monthly market updates, financial insights and inspiring travel ideas.

.

Sign up now

Receive tips

Give us a call

(719) 394.3900
(844) 295.0069