Understanding Medicare - What to Know Before Signing Up

Pamela Turner • February 24, 2025

Here's the three things you absolutely need to know before you enroll in Medicare:

Do you understand YOUR personal timeline?
Why you need to go on an "information diet" (and what that means).
The only two plan types you need to know to make a decision.

This is going to pinpoint exactly what you need to do and when, so you can stay focused and avoid costly mistakes.

(*If the video won't play, watch directly on YouTube HERE)

Think About It Like Car Shopping…

If you’ve ever gone car shopping, you know how overwhelming it can be. The endless choices, the pushy sales tactics, and the fine print can leave you exhausted.

And that’s why you have to be prepared before car shopping. You need to know what you can afford, what financing looks like, and what to expect, so you don’t get taken advantage of.

Medicare works the same way.

You wouldn’t just walk into a dealership without doing any research. So why would you sign up for Medicare without first understanding how it actually works?

Step #1: Understanding YOUR Medicare Timeline

The first thing you need to figure out is when to sign up for Medicare. Your timeline depends on a few key factors:

Turning 65 soon? You can sign up starting three months before your 65th birthday month. If you’re already collecting Social Security, you’ll be automatically enrolled.
Still working past 65? You might be able to delay Medicare, but only if your employer coverage qualifies.
Is your employer small (fewer than 20 employees)? If so, you must sign up for Medicare at 65, because Medicare becomes your primary insurance. If you don’t enroll, you could end up responsible for 80% of your medical bills!
Have an HSA (Health Savings Account)? If you plan to keep working past 65 and want to keep contributing to an HSA, you need to hold off on signing up for Medicare Part A. Medicare will retroactively backdate your coverage by six months when you enroll, which could cause tax penalties if you’ve been contributing to an HSA during that time.

Your Medicare timeline is critical to get right. Missing deadlines or misunderstanding the rules can cost you big time, in weird pitfalls like the ones mentioned above.

That’s why I created my 2025 Medicare Workbook, which walks you through the exact steps you need to take.

Request your Free 2025 Medicare Workbook by clicking the button at the bottom of this post.

Step #2: Go on an “Information Diet”

Quick question: Do you know the parts of Medicare?

If you’re like most people, the answer is: "kind of?" Maybe you’ve heard of Part A and Part B, but what about Part C and D? And then there are all those lettered Medigap plans.

It’s a lot.

And the problem is, Medicare information is everywhere. Mailers, commercials, phone calls - and most of it comes out of order, making it nearly impossible to make sense of it all.

That’s why I tell my clients to go on an information diet.

That means stop trying to learn everything at once. More information isn’t always better. You just need the right information, in the right order.

Here’s the simple breakdown:

Part A = Hospital coverage (room & board for inpatient stays).
Part B = Doctor visits, outpatient care, ER visits, and surgeries.
Part D = Prescription drug coverage (you must buy this from a private insurer).

Part A & B together make up Original Medicare—and these two parts form the foundation of your coverage.

Part C is Medicare Advantage, an optional plan which gets a mention in Step #3.

Once you understand these basics, then you can move on to learning about your two Medicare coverage choices:

Step #3: Learn the Two Plan Types

Here’s the most helpful thing you might learn today: There are only TWO paths you can take with Medicare.

Most people are shocked when they hear this because they’ve been drowning in information and assumed there were dozens of choices. But the truth is, everything boils down to two paths:

Path #1: Original Medicare plus a Medigap (Supplement) Plan

You pay a monthly premium for a Medigap plan.
You can see any doctor that accepts Medicare, nationwide.
You’ll have little to no out-of-pocket costs when you get medical care.
You’ll need to buy a separate Part D prescription plan.

Path #2: Choose a Medicare Advantage Plan (Part C)

Many plans have a $0 extra monthly cost.
You’ll have copays and out-of-pocket costs when you get care.
You’ll need to use a network of doctors and hospitals.
Your prescription drug coverage is usually included in the plan.

These two paths are complete opposites.

Medigap = More monthly cost, but fewer out-of-pocket expenses when you need care.
Advantage = Lower (or $0) monthly cost, but you pay as you go with copays and network restrictions.

Neither option is right or wrong. It just depends on your needs and preferences.

For example, if you travel often, Medigap gives you more flexibility. But if you prefer a lower monthly cost and don’t mind network restrictions, Advantage might be a better fit.

The key is understanding the trade-offs so you can confidently choose what’s best for you.