Turning 65 in Retirement – What To Do for Medicare

If you’re ready for Medicare and turning 65, there are a lot of complex topics that you must think about. In our latest episode of Secure Your Retirement, we had our very own Shawn Southard back on the show to help folks reaching the age of 65. 

You’ll be able to go on Medicare at 65, but it’s overwhelming looking through plans and options. 

We’re going to walk you through the entire process to help you start to understand Medicare, how it fits into your retirement planning, and the steps you can take to make the whole process easier on you. 

What is the Initial Enrollment Period (IEP)? 

IEP has a seven-month window, starting three months before turning 65, where you can enroll in a Medicare plan. You can apply for Part A, which is for in-patient care and Part B, which is for doctor visits and outpatient care. 

Special Enrollment Period (SEP) 

An SEP is becoming more common as more people are working past the age of 65. While you’re still working, you’ll forget about Medicare when turning 65 and remain on your health insurance plan until you retire. 

Once you do retire, the IEP is likely to go by, so you’ll fall within the SEP.  

You can fall into the SEP for a few reasons, but the most common is that you worked past your IEP and now need coverage because you’re off your group insurance plan. 

Note: You have eight months from the time you retire to enroll in a plan within the SEP, or you will face penalties. 

General Enrollment Period (GEP) 

Imagine that you go to Cancun in your mind and aren’t paying attention to the IEP or SEP. You can still get into Medicare during the GEP, which is January 1st – March 31st each year. You can enroll in Parts A and B at this time. 

Medicare also changed the rules a bit, and if you sign up in January, you’ll begin receiving your benefits on February 1st, not July 1st, which used to be the case.  

Depending on when your IEP and SEP passed and your situation, you may receive a late enrollment penalty. Shawn works with folks to help navigate these situations on an individual basis. 

Scenario: Still Working, turning 65, and Still Enrolled with My Employer’s Plan 

If you’re approaching 65 and plan on working a few more years, you need to make sure that your company plan has 20 or more people actually enrolled in the plan. It’s not enough for 20 people to be working at the company – they need to be enrolled in the health plan. 

In this case, Medicare will provide an exception and won’t need to do anything with Medicare. 

Employees of employers with a health plan that has 19 enrollees or less will need to enroll with Medicare, even if they plan on continuing working past 65. 

Scenario: Retired But with Health Coverage 

In some cases, a person will retire before 65 and still receive benefits from their employer. For example, state employees of North Carolina can still receive their benefits until 65, but these benefits are considered secondary when you hit 65. 

You will need to enroll in Part A and B of Medicare at 65, even if you want to keep your former employer’s health insurance. 

Scenario: I’m Still Working, Approaching 65, But I Receive Social Security Retirement Benefits Already 

If you’ve been receiving Social Security or Railroad retirement benefits for at least four months before you reach 65, you’ll automatically be enrolled in Medicare Part A and B when you hit 65. 

You will want to send the coverage back to Medicare when you receive your Medicare card. 


Medigap plans have no medical underwriting for the first six months of your Medicare coverage, and you’ll pass by the six-month period because of the automatic enrollment. Even if your coverage starts for one day, the time for Medigap plans will start ticking down. 

How Do You Enroll in Medicare? 

If you’re reading this and thinking, “I need to enroll,” you have a few ways to do this. An easy way to enroll is to: 

You can also go down to any Social Security Administration office and enroll in Medicare in person. 

For many people, the ideal solution is to go through the online portal. 

What Forms and Documents Do I Need for This to Go Smoothly? 

You should have a few things available: 

  • Social Security number 
  • W-2s  
  • Proof of citizenship (Birth certificate, passport, etc.) 
  • CMS Form (if you work past 65) 

Shawn can help you obtain all of the forms you need when you work with him. 

Penalties for Missing the Enrollment Period 

If you miss the enrollment period, you will be penalized. Penalties cannot be undone, so they’re monthly, lifetime mistakes. For example, if you miss Part B coverage, you’ll pay 10% on top of the premium for every 12 months that you miss it. 

You’ll be paying 10% more monthly for the rest of your life. 

Let’s say that you didn’t enroll until 60 months after your enrollment period. This means that you’ll be paying an additional 50% on top of your premiums forever. 

The Part D (for drug plans) late enrollment penalty is 1% for every month that you weren’t enrolled in one for the rest of your life. Shawn knows a client that didn’t enroll in a prescription drug plan at 65 because he didn’t need medication at the time. When he turned 70, he needed medication, and he now pays a 60% penalty on top of the normal plan price. 

Anyone listening to this will want to avoid being penalized because it will impact you for the rest of your life. 

You can handle Medicare on your own, but if you work with Peace of Mind Wealth Management to secure your retirement, Shawn is our Healthcare Professional Specializing in Medicare and is available to help all our clients. 

Working With Shawn Using the K.I.S.S. Acronym 

Shawn follows the Keep it Simple Shawn mindset, and he aims to provide a calm approach throughout the process. He will work with you wherever you are in the Medicare process, discuss your goals, and help you find the coverage and plan that is best for you. 

He uses a flowchart to show people the: 

  • Foundations of Medicare 
  • Options of Medicare 

You’ll also learn about Medicare plans, Medigap, payments, Income-related Monthly Adjustment Amount (IRMAA) and other aspects of Medicare. Shawn will also hop on calls with your employer to make the process as seamless as possible. 

If you do want to talk to Shawn about Medicare and begin working with him, feel free to reach him at our office at (919) 787-8866 or email him at shawn@pomwealth.net.