Medicare: How To Enroll

Dear Nana,

I have been working to understand Medicare insurance so that I can explain it to you and your friends. This market is confusing, as are many insurance topics. I feel that the way technology is improving the world today at such a rapid pace, your generation is being forced to adapt to “improvements” that don’t seem to suit the lifestyle you’ve grown fond of.

These letters are for you to learn the basics, if you need more explanation, I’m always a phone call away. I was given an office phone, put my number in your contacts: 701-478-0113

I want to tell you what Medicare is, and how it can help protect your dream for a happy retirement. In my last letter I shared when to enroll, and now I will share how to enroll.


The Medicare enrollment process looks different for each individual, but there are two processes that everyone follows in some form. I’ll refer to these as Original Medicare enrollment and Medicare Supplement enrollment.

Original Medicare Enrollment

This process is for starting your Part A (Hospital) and Part B (Medical) insurance. If you are enrolled in social security benefits before turning 65, this will automatically occur. If you aren’t receiving social security, you must manually sign up.

To sign up for Parts A and B, you can visit or call your local Social Security office or sign up online at ssa.gov. Parts A and B are creditable health coverage, you are required to have creditable health AND drug coverage to avoid Medicare penalties.

Medicare Supplement Enrollment

Medicare Supplement enrollment is a process that is unique for each individual enrollee. Original Medicare does not cover all potential health risks, which leads many consumers to purchase supplemental insurance plans. To enroll in supplements, you must be eligible for Parts A and B, with most supplements requiring you to be enrolled in Original Medicare.

To identify which options are right for you consider visiting Medicare.gov, reading the Medicare and You handbook, or consulting a professional.


This is basis for an understanding, but only an introduction. Call me, write me, or message me and I will share more of my learning with you.

I hope to see you soon,

Dylan