If Medicare has your head spinning, you’re not alone. Every day, people just like you are typing things into Google like:
“Do I need Medicare if I’m still working?”
“What’s the difference between Medicare and Medicaid?”
“Is Medicare free?”
With all the marketing, telephone calls, and complicated systems surrounding the Medicare experience, it’s okay if you have a few (hundred) questions. That’s why I am here! I love to help people with Medicare, and it gives me great joy to help you get the care you need with a Medicare plan that works for your budget.
So today let’s clear the confusion. I’m Medicare Dana, and I’ve helped hundreds of people just like you understand their options, avoid costly mistakes, and feel confident about their coverage. Here are the top Medicare questions I hear all the time, along with the explanations you’ve been searching for.
1. When should I sign up for Medicare?
If you're turning 65 soon, your Initial Enrollment Period (IEP) starts 3 months before your birthday month, includes your birthday month, and ends 3 months after.
But! If you're still working and have credible health coverage, you might not need to enroll in everything right away. (P.S. I can help you figure that out.)
2. What is the difference between Medicare Part A, B, C, and D?
Great question. Think of it like this:
- Part A = Hospital stays
- Part B = Doctor visits & outpatient care
- Part C = Also called Medicare Advantage – it bundles A + B and usually D
- Part D = Prescription drug coverage
You can mix and match or go the all-in-one route. I’ll help you compare.
3. Do I need Medicare if I’m still working?
Maybe. It depends on how you receive health coverage while you are working. If you are enrolled in your employer’s medical plan and your employer has 20+ employees, you might be able to delay Part B without penalty.
But if your coverage is not considered "credible" or your company is small (less than 20 employees), you may need to enroll in Medicare where Medicare might become your primary insurance—even if you're still on the clock.
Another important factor that impacts the decision to enroll in Medicare is whether or not you are contributing to a Health Savings Account (HSA).
Every situation is different. Let's check yours together so you don’t accidentally pay more later.
4. Is Medicare free?
Only Part A is usually free if you’ve worked and paid into Medicare for 10+ years.
Part B comes with a monthly premium (in 2025, it’s about $185/month, depending on income).
Parts C & D vary depending on your plan.
Let’s just say: Medicare isn’t free, but it can be much more affordable if you shop for the right plan that fits your needs!
5. What’s the penalty if I don’t sign up on time?
The late enrollment penalty is real—and it sticks with you for life.
If you miss your enrollment window for Part B or Part D, you could pay extra every single month for the life of your time on Medicare.
Good news: I can help you avoid that.
6. Should I get a Medicare Supplement or a Medicare Advantage Plan?
That depends on:
- How much you travel
- Whether you want to pick your own doctors
- How comfortable you are with co-pays vs. higher premiums
Some folks want predictability with a Medigap (Supplement) plan. Others like the lower premiums upfront and extras in Advantage plans. There’s no one-size-fits-all answer—just the one that’s right for you.
7. Can I change my plan later?
Depends on your health. You have one ‘free’ pass to receive a Medicare Supplement/Medigap plan without medical underwriting or acknowledgement of pre-existing conditions, at your Initial Enrollment Period IEP (or for some in their Special Enrollment Period SEP).
Once that period has passed, you can make a change any day of the year for the Medicare Supplement/Medigap plan, if you can pass medical underwriting. The advantage plans have no medical underwriting; however, they have lock in periods and only certain times of the year you can make a change.
One is during Medicare’s Annual Enrollment Period (Oct 15 – Dec 7). There are also Special Enrollment Periods if your circumstances change (like moving, losing employer coverage, etc.)
Tip: Don’t sleep on your review. Medicare Advantage and Part D Drug Plans change every year—and what worked last year might not be your best option now.
8. What if I have a chronic illness or take expensive medications?
This is when it really counts to be working with a trusted advisor. There are specific plans that cover more for people with chronic conditions like diabetes, heart issues, or even cancer. The same goes for prescription-heavy plans.
If you're concerned about costs, let me help! I take your entire list of medications and use a plan finder to show you which one saves you the most.
9. Do I have to talk with someone, or can I just sign up online?
Technically, yes — you can sign up online through a carrier or Medicare.gov. But the better question is: Should you?
Absolutely not.
Medicare is not something anyone should tackle alone. It's not just a form or a plan, it’s your healthcare, your finances, your peace of mind. And the truth is, one wrong choice, even a single overlooked detail, can end up costing you thousands or leave you without the coverage you thought you had.
That’s why having a trusted Medicare agent matters.
When you work with an independent Medicare agent, you’re not just signing up for a plan, you’re gaining an advocate. Someone who walks the Medicare maze every single day. Someone who understands the fine print, keeps up with the changes, and makes sure you're making informed, confident decisions.
And here's something most people don’t realize:
Working with a licensed Medicare agent costs you nothing extra. Agents are compensated by the insurance carriers, not by you. So, you get expert help, personal guidance, and ongoing support at no additional cost.
What does that look like in real life?
- It means having someone to call when you get a confusing bill in the mail.
- It means knowing whether or not you’ll need referrals, prior authorizations, or if your doctor is actually in-network.
- It means staying ahead of deadlines, changes, and penalties you didn’t even know existed.
- It means having someone in your corner — not a 1-800 number.
Medicare isn’t one-size-fits-all. Your health, your budget, your lifestyle, they’re all uniquely yours. And that’s exactly how your Medicare coverage should be handled: personally.
So yes, you can go online and sign up alone.
But when it comes to something this important, why would you?
10. Why work with Medicare Dana?
I’m independent—so I work for you, not the insurance companies.
I’ve helped hundreds of people feel confident, not confused.
I make Medicare make sense—without the jargon.
My help? It’s free. Really.
Don’t Google it Alone
Medicare isn’t one big government plan that is the same for everyone. It’s a mix of choices, costs, and timelines. But you don’t have to figure it out alone. I’ll help you compare plans, save money, and enroll with confidence.
Give me a call today or email me at [email protected].