Transitioning into Medicare can be stressful. While the subtitle is a bit tongue in check, simplifying Medicare can be achieved.

The following is intended to provide you with the important highlights regarding your onboarding to Medicare. For a more in-depth study, I suggest you procure a copy of “Navigating Medicare” by my good friend and co-worker, Hillary Broome.

Following are the major questions we get from our clients aging into Medicare:

  • When should I start the Medicare process?
  • What are my coverage choices?
  • If I continue to work, what should I do?
  • Can I bypass Medicare?
  • Do I really need a Drug Card?
  • How important is all this mail I’m getting?

Important Dates:

Your Medicare coverage will begin the 1st day of your 65th birth month. If your birthday is the 1st day of your 65th birth month, your Medicare coverage will begin the month prior to your 65th birth month.1

When should I begin the process? You can actually enroll in a Medicare solution three months before your 65th birth month. However, I suggest you begin your learning journey a minimum of six months before your 65th birth month. This will give you ample time to learn of the various coverages, seek professional advice and enroll in the plan(s) of your choosing.

Missed enrolling prior to your birth month? No worries, you may enroll in any of your options during the next three months. This seven month period of time is called Initial Enrollment Period (IEP).

Once you reach age 65, your Medicare choices are:

Remain on your group plan if you continue to work2
If you aren’t working, enroll in Medicare Part A, B and we strongly suggest Part D. Decide between either a Medicare Supplement or a Medicare Advantage plan (which may have Part D embedded in the benefits)

“This Medicare insurance is too expensive, I need something else.” A few years ago, one of my clients, whom I had assisted in their transition into Medicare, called me with the above request. For their circumstances, the answer was, “there are no substitutes for Medicare.”

Every person’s needs can be different based on employer benefits, veteran’s benefits, and income levels, to name a few. I strongly urge being proactive. Begin your learning early and sit down with someone who specializes in Medicare.

“I don’t take any drugs, why should I buy a Drug Plan?” (Medicare Part D). There are two answers:

Your situation may change. Generally speaking, once you’ve missed your IEP, you can only enroll in a Part D plan during Annual Enrollment (10/15-12/7) each year. For every month you delay enrolling in a Part D plan, you will incur a permanent penalty, paid when and if you enroll in a Part D plan.3

Your Medicare Junk Mail Survival Plan:

Our First Impressions Associate paged me, advising that my next appointment had arrived. As I walked out of my office and rounded the corner, I encountered a well groomed, well dressed lady clutching a large bag and a look of guarded hope on her face. We exchanged introductions and I asked her to follow me into my office. As we set down, she began unpacking the bag and stacking scores of mailers, post cards, and thick envelopes onto my desk. Finished, she looked at me and said, “Please tell me what of this is important.” I asked her if she had her Medicare card, which she quickly produced. After confirming she did indeed have her Medicare card, I stood up, leaned over the desk and pushed the entire pile of junk mail off onto the office floor. I sat back down, looked at her and asked, “Do you feel better?” Her look of puzzlement quickly turned to one of amused relief and said, “Yes!”.

The moral of the story? The overwhelming amount of mail you get as you approach your 65th birthday is marketing materials and you don’t need them. What you do need is an hour or so with an Advisor who understands Medicare.

WARNING: Don’t throw any of it away, however, until you get your Medicare Card and choose a coverage solution. After you turn 65, the volume of marketing materials should diminish, leaving you with only official, Medicare and Insurance information to process.


2If you work for a company that employs fewer than 20 employees, get your coverage benefits in writing from your insurance company. The rule for employers with less than 20 employees is that Medicare is PRIMARY. If you don’t buy Medicare Part B, you could have gaps in your coverage.