Are you getting ready to go on Medicare? If so, you’ve probably found out by now how many important Medicare decisions you have to make (A LOT!). And if you’re like most people, you want to make the right Medicare decisions because they’ll affect your future. But with so many options and opinions out there, it can be hard to know which decisions are the right ones. 

That’s why today, we’re going to show you four important steps you need to take as you approach Medicare. If you follow these steps, you'll not only make the right Medicare decisions for your future, but you’ll also protect yourself from making Medicare mistakes that could cost you dearly. 

Approaching Medicare: 4 Important Steps

Here are four key steps to take when approaching Medicare. They’ll help you make the right Medicare decisions and protect you from costly mistakes. 

Step 1: Get Educated

First and foremost, you need to get educated about Medicare. Before you make any important decisions, you have to understand what you're doing and why so you can avoid mistakes and have confidence that you’re making the right Medicare choices. 

But here’s the thing. There is no lack of information about Medicare. In fact, the closer you get to 65, the more information and advice you’ll hear about Medicare, from ads in your mailbox and email inbox to commercials on TV and pushy insurance agents calling you up on the phone. Unfortunately, most of this “information” only wants to sell you something. So how can you trust that it’s reliable? You can’t.

The second way you can try to become educated about Medicare is by going online. You can spend hours sorting through the millions of resources out there on Medicare to try to find credible information that 1) isn’t trying to sell you something and 2) answers your questions. After all that searching, you might feel a bit more aware of the Medicare process, but you will almost certainly feel overwhelmed and unsure of the right steps to take. 

Third, you might ask friends and family about their Medicare decisions and try to comb through their answers to find out what will work for you. But the problem is, Medicare isn’t one-size-fits-all. Your friends and family have different health needs, take different medications, and see different doctors than you, so what worked for them may not work for you. 

Most people relying on these three routes to learn about Medicare end up confused and overwhelmed. That’s why we’ve created, a one-stop-shop for all your Medicare questions. You’ll never be overwhelmed with too much information or ever once have to hear a salesy pitch on which plan you should go with. Instead, you’ll get a clear, easy-to-understand, and unbiased education covering everything you need to know about Medicare. 

Step 2: Enroll Into Medicare A and B

The second step you need to take is deciding whether you’re going to enroll in Medicare A and B, and if so, when you’re going to enroll. 

Now if you’re retired, there’s really no decision to make. You will have to enroll in Medicare A and B since you have no employer coverage options. If you’re on Social Security, you’ll automatically be enrolled in Medicare A and B. In fact, your Medicare card will show up about 90 to 100 days prior to when your coverage begins. If you're retired but not on Social Security, you will still enroll in Medicare A and B but you’ll have to self-enroll to initiate the process. 

However, for those of you approaching 65 and still working, you’ll have to decide if enrolling in Medicare A and B is a good choice for you. Many people opt to wait until retirement to enroll in Medicare, while others take Medicare right when they turn 65. Here’s how to decide which choice is best for you: Compare your work plan with Medicare. 

Here are a few things to consider:

    • Look at Premiums: How much are you paying (the amount coming out of your paycheck) for your work plan premium? 
    • Consider Coinsurance: How does your work plan coinsurance compare to Medicare? Is it an 80/20 or 90/10 system? 
    • Determine Deductibles: What is your work plan’s deductible? How does it compare to Medicare deductibles?
  • Review Max-Out-of-Pocket Amounts: Compare your work plan’s max out of pocket amounts to those of Medicare’s. Are you at greater financial risk on your work plan or on Medicare?
  • Consider Medications: Does your work plan cover all your medications? If not, will Medicare cover medications your work plan doesn’t?  


If your present work plan costs you more than Medicare coverage and offers less than what Medicare will offer, it may be in your best interest to enroll in Medicare A and B when you turn 65, even if you’re still working. 

One important caveat here is if you have children or a younger spouse who are covered by your work plan. If so, they will no longer have coverage when you get on Medicare. In this case, we would strongly encourage you to stay on your work plan until you retire. 

Step 3: Decide Between Advantage and Supplemental Plans

The third step you’ll need to take is to decide between an Advantage and Supplemental Plan. This decision only applies to those who’ve decided to enroll in Medicare A and B. 

Once you’ve made the decision to enroll, you only have two insurance options beyond Medicare A and B, the Advantage plan (called replacement plans), and the Supplemental plan. 

Advantage plans are called Medicare C plans, and when you take one of these you’re actually replacing Medicare A and B coverage and working directly with a private insurance company. Medicare C plans typically include a prescription drug plan, and have very low or zero monthly premiums. 

The other option is to take a Supplemental plan, also called Medigap policies. Supplemental plans, unlike Advantage plans, do not replace Medicare A and B. Instead, they leave Medicare in the first payor position, and simply fill in the coverage gaps left by Medicare. If you go the Supplemental plan route, you’ll have to purchase a separate Part D plan for your prescription drug coverage. 

Supplemental plans charge you monthly premiums in exchange for covering the gaps in Medicare A and B. Advantage plans, on the other hand, operate on a co-pay system. So with Advantage plans, instead of paying monthly premiums, you’ll pay more (in co-pays) for doctor visits, prescriptions, and other health services. 

Step 4: Seek Enrollment Assistance

The final step you need to take when approaching Medicare is to seek enrollment assistance. Most people don’t want to navigate additional insurance enrollment on their own, so they look for professional help. 

There are only two options when it comes to enrollment help. First, you can use a captive agent. Captive agents are employees of one single insurance company, hence the name captive. Because of this, they have limited insurance options. Why? Captive agents only have access to the products sold by their company. Typically, this means captive agents can only offer you two or three different plans. 

Since captive agents are only trained to sell the two or three plans their company offers, they typically have very limited knowledge of Medicare and the different types of plans available. In other words, their one goal is to sell you their company’s plan, then move on to the next caller. Because of this, they typically don’t offer clients any other Medicare/insurance assistance or knowledge. 

The other option is to use a broker. Brokers do not sell for one single insurance company. Instead, they have access to a vast amount of products, meaning they are able to compare numerous plans to find the one that will work best for you. 

Since brokers are not just trained to sell a single company’s products, they typically have much more knowledge of insurance and Medicare and are able to answer your questions and give you assistance, not just sell you a plan. 

And the good news is, it’s illegal for both captive agents and brokers to charge for their planning services, so there’s really no reason why you shouldn’t seek professional help. We strongly urge everyone to work with a qualified, highly-trained broker to help you with the Medicare enrollment process. If you would like enrollment help, visit to speak with one of our Medicare School guides.


There are numerous decisions you’ll have to make when you’re approaching Medicare eligibility. If you feel overwhelmed or unsure of which decision to make, follow the four steps we laid out:

  • Get educated
  • Decide if you’re going to enroll in Medicare A and B
  • Choose between an Advantage and Supplemental plan
  • Seek enrollment assistance

If you’re approaching Medicare and want more help, we recommend connecting with a Medicare School Guide. Medicare School Guides help countless people just like you navigate the Medicare process and make the right decisions for their future.

We take the stress and confusion out of the Medicare process by helping you compare plans, enroll in Medicare (and additional coverage) at the right time, and sort through all the necessary paperwork so the process is painless and hassle-free.

To take the next step, watch our full course here, or schedule a free one-on-one call with a certified Medicare School Guide who can answer your questions, compare plans options, and even help you enroll. Click here to get started.


If you’re tired of conflicting and confusing Medicare information, sign up for our free workshop today.

You’ll learn everything you need to know about Medicare to feel confident about choosing the best plan.

Get the Free Workshop started in 2009 to provide an unbiased and education-focused service to individuals approaching Medicare enrollment. Since then, has helped over 100,000 people find and enroll in the best Medicare plans that fit their budget.