Turning 65 is a major milestone — but for millions of Americans, it also means stepping into one of the most confusing decisions of their lives: enrolling in Medicare. Between Parts A, B, C, and D, supplement plans labeled with every letter imaginable, and a mailbox overflowing with insurance flyers, it’s no wonder so many people feel overwhelmed.
On the latest episode of the Cg Business Advisor Podcast, host Scott Seidenberg sat down with Mike Lewis, FACMPE, MBA, Partner in Cg’s Healthcare Services Group and a healthcare professional with more than 45 years of industry experience, to break it all down. Before joining Cg, Mike spent 27 years as a senior healthcare executive managing medical practices of every kind — primary care, internal medicine subspecialties, and surgery. Today, he helps clients cut through complexity and make smart, informed decisions about their healthcare.
Here’s what you need to know.
What Is Medicare, Exactly?
At its core, Medicare is a federal health insurance program — but it covers more people than
many realize.
“Medicare is a federal health insurance program for people 65 and older and for individuals with certain disabilities, including end-stage renal disease and ALS,” Mike explained. The program was signed into law in 1965 and implemented in 1966, meaning it has been a fixture of American life for more than 60 years.
When to Enroll: The Initial Enrollment Period
The clock starts ticking well before your 65th birthday. Medicare’s Initial Enrollment Period is a seven-month window — starting three months before you turn 65 and ending three months after. Signing up is relatively straightforward. You can apply online, or, as Mike noted, “Some people find it easier to make an appointment with their local Social Security Administration office where one of the team members there will help walk you through the application.” The bigger question isn’t how to enroll — it’s which path to choose.
The Alphabet Soup: Understanding Your Options
This is where Medicare earns its reputation for being confusing. Mike broke the choices down into two main paths.
Path 1: Traditional Medicare
Traditional Medicare has two core components:
- Part A – Covers hospital and nursing home bills
- Part B – Covers outpatient services like doctor visits, radiology, and laboratory work
If you go the traditional route, you’ll typically also want to add:
- A Medicare Supplement plan (also known as Medigap), which helps cover costs
Medicare doesn’t - Part D, which covers outpatient prescription drugs — something Mike strongly
recommends for nearly everyone
One important note on supplement plans: they are standardized by the federal government and identified by letters (Plan G, Plan N, and so on). That means the benefits of an AARP Medicare Supplement Plan G are identical to a Cigna Medicare Supplement Plan G. The only real
difference? The premium each insurer charges — which, as Mike dryly observed, rarely comes with a rational explanation.
Path 2: Medicare Advantage (Part C)
Introduced by Congress years after the original program, Medicare Advantage plans — also called Part C — are offered by private insurance companies like Aetna, Cigna, and Humana. Instead of enrolling in traditional Medicare, you enroll in one of these plans. Key differences between the two paths include:
- Referrals: Medicare Advantage plans may require a referral to see a specialist; traditional Medicare never does.
- Premiums: Some Medicare Advantage plans carry a monthly premium on top of the
standard Part B premium. - Out-of-pocket limits: Medicare Advantage plans typically cap your annual out-of pocket costs. Traditional Medicare has no such limit.
- Extra benefits: Many Medicare Advantage plans include perks like hearing aids, vision coverage, or fitness memberships — benefits traditional Medicare doesn’t provide.
Medicare Isn’t Free — and Premiums Are Income-Dependent
One of the most misunderstood aspects of Medicare is the cost. The current base premium for Medicare Part B is $202.90 per month — but that’s just the starting point. “The premium is income dependent,” Mike explained. “The base premium is $202.90, but it can go all the way up to $690 a month for Medicare Part B.” How is that determined? The government looks at your tax return from two years prior. So in 2026, your premium is based on your 2024 income.
Good news: If your income has dropped significantly — say, because you’ve retired — you can file an appeal at the Social Security office, and in many cases, they’ll reduce your premium. When you stack up the Part B premium, a Medicare Supplement premium, and a Part D
prescription plan, traditional Medicare adds up to a considerable monthly cost. That said, it also offers the most freedom of choice — which is why many people still prefer it.
Still Working at 65? You Have Options.
Not everyone retires at 65, and Medicare rules reflect that. “If you or your spouse is working for a company with more than 20 employees that offers a group health insurance plan, the group health insurance plan becomes primary to Medicare,” Mike said.
This is known as the TEFRA provision. Many people in this situation continue with their employer’s group coverage and elect to pick up Medicare as a secondary plan. It’s an option a lot of people don’t know exists — and one worth exploring carefully before making a decision.
Watch the Fine Print
When it comes to choosing between plans, the details matter enormously. Mike offered a powerful example:
Some Medicare Advantage plans advertise no additional premium beyond what you’d already pay for Part B. Sounds great — until you dig into the details. You might discover a $250-per-day copay for the first five days of each hospitalization. That’s $1,250 per hospital stay out of your pocket.
“Let’s say you’re a patient who has chronic obstructive pulmonary disease, congestive heart failure, and you’re hospitalized two or three times a year. Well, that may be an additional $2,500 out of your pocket that you have to take into consideration when you price out what these plan are going to cost you.” The lesson: the cheapest premium isn’t always the cheapest plan.
Mike’s Biggest Piece of Advice
So what’s the single most important thing for someone approaching 65?
Don’t react to the first person who tries to sell you something.
Because Medicare is a government program, no one earns a commission when you enroll in basic Medicare. But Medicare Supplement plans and Medicare Advantage plans? Those often come with broker commissions — which can, in some cases, influence which plans get pushed
hardest.
Mike isn’t dismissing insurance brokers — they provide real value and are entitled to be paid for their expertise. But he emphasized that consumers should go in informed, ask questions, and read the fine print, including any pre-existing condition limitations or surcharges (several plans still surcharge smokers or those with a long history of smoking).
His practical tip: as you approach 65, your mailbox will overflow with flyers from every insurance company imaginable. Instead of feeling buried, lay everything out side by side and ask yourself what matters most to your situation — your medications, your doctors, your hospitalization risk, your budget.
There are also excellent free online resources that let you compare plans and even plug in your current prescriptions to see how different Part D plans would cover them. Most people simply don’t take advantage of them.
The Bottom Line
Medicare is one of the most valuable benefits Americans can access — but it arrives at a stage of life when decision-making can feel overwhelming, and the stakes are real. “It is unfortunate that we take people who are at a fragile time in their lives and make them subject to some of the most complicated healthcare decisions that they will have to make,” Mike reflected. “It’s very confusing.”
That’s exactly why working with a knowledgeable professional can make all the difference.
Get in Touch
If you have questions about Medicare enrollment, plan selection, or any other healthcare financial decision, Mike and the team at Cg are here to help.
- Email Mike Lewis: mlewis@cgteam.com
- Offices: Toms River and Tinton Falls, NJ
- Learn more about Cg’s Healthcare Services at: cgteam.com
Listen to the full conversation on Episode 80 of the CG Business Advisor Podcast, wherever you get your podcasts. Learn more at cgteam.com. © 2026