Serving Nashville, TN · Davidson County
Turning 65, still working, or coming off an employer plan? Medicare isn’t one decision — it’s a short list of deadlines, and missing one can follow you for life. The Jordan Insurance Agency works with Medicare clients across Nashville, and our office is downtown on 4th Avenue North.

Why the help matters
Search for Medicare help in Middle Tennessee and almost everything you find is addressed to “the Nashville area.” That is a region, not an address. Davidson County is its own county, and Medicare Advantage and Part D availability can vary by county and ZIP code — so what is on offer for you is not automatically what is on offer for a neighbour in Williamson or Sumner. The narrower questions are the ones that decide it: which doctors you intend to keep, which prescriptions you take, and which enrollment window you are standing in today.
✕A national 1-800 number
Big 1-800 lines send you to whoever is available, working from a script. Call again and you get someone new. Your doctors, your prescriptions and your history start over every time.
✓The Jordan Insurance Agency
One licensed, local agent learns your situation once. We check the doctors and prescriptions you already have, and compare options from several companies. Next year, you call that same person by name. Our help costs you nothing.
Who this page is for
Your enrollment window opens three months before your birthday month. We’ll show you what has to happen inside it and what can wait.
Where to start →Nashville has a lot of people working well past 65. Whether you can safely delay Part B depends on specifics most people are never told.
Where to start →Leaving employer coverage starts a clock. This is the one people most often plan a month too late.
Where to start →Three major systems operate across Nashville. It is common for one household to use two of them, and that is worth sorting out first.
Where to start →Coverage changes from year to year, and so do your prescriptions and your doctors. An annual look is worth the half hour.
Where to start →Adult children handle a lot of these calls. With your parent’s permission, you’re welcome to sit in and ask the questions.
Where to start →Nashville, and the three-system question
Vanderbilt, Ascension Saint Thomas and TriStar all operate across Nashville, frequently within a few minutes of each other. A household here can easily end up using two of the three — primary care in one, a specialist or a hospital in another. That is a different conversation from the one in a county with a single dominant hospital, and it is the reason we write down the doctors you want to keep and check them one at a time against your actual address before anything is suggested.
The decisions, one at a time
There is no single “best” path through Medicare. What’s right depends on your doctors, your prescriptions, how much you travel, and what you want your costs to look like. Here is how we work through each piece.
Your Initial Enrollment Period generally runs seven months — the three months before your birthday month, your birthday month, and the three months after. Two things trip people up. First, enrollment isn’t always automatic. If you’re receiving Social Security benefits at least four months before you turn 65, Medicare generally enrolls you in Part A and Part B for you. Otherwise you usually need to take action to enroll. Second, waiting until your birthday month can push your start date later than you expected.
Come with three things and this gets easy: the doctors you want to keep, your current prescriptions with doses, and whether you or your spouse are still working. If you’d rather read the timing first, here is when you can enroll in Medicare.
Whether you can delay Part B without a late-enrollment penalty depends on your specific situation, including whether you have group health coverage based on your own or your spouse’s current employment. Employer size can also affect how Medicare coordinates with that coverage, so we check the details before you decide.
Staying on an employer plan past 65 is common in Nashville — at a hospital system, a university, a music-business employer, or part-time after a first retirement. When you do retire, losing that coverage generally opens a Special Enrollment Period, but it doesn’t stay open indefinitely. The cleanest handoffs are planned a month or two before your last day. Our write-up on working past 65 and employer coverage covers how the two fit together.
Three questions come up constantly: when should Part B start, can I delay it while I’m working, and what happens the month employer coverage ends. The reason we push people to ask early is that Part B carries a late enrollment penalty which, once it attaches, generally stays with you for as long as you have Part B. It is not a one-time fee.
We’d rather spend twenty minutes on this before your deadline than explain it afterward — and in Nashville you can spend those twenty minutes in our office if you’d prefer. For background, read the late enrollment penalty and how Medicare works alongside employer coverage.
Drug coverage is its own decision with its own timing. Going without creditable prescription drug coverage after you’re first eligible can bring a late-enrollment penalty of its own, which is why “I don’t take anything right now” isn’t quite the whole answer.
The practical step is simple: bring your actual prescription list, names and doses, not a rough memory. Plenty of people downtown fill near work rather than near home, so tell us where you actually pick things up. Here’s how Part D works.
A supplement works alongside Original Medicare and helps with costs Original Medicare leaves behind. Medigap plans are standardized by letter, so the basic benefits for a given plan letter are the same from one insurer to the next. Premiums, underwriting, discounts and company service can still differ — which is where the comparison actually happens.
For a Nashville household using two different health systems, the appeal of this structure is usually that it does not route care through a single network. Whether that fits how you actually use care is the real question, along with the health-questions issue if you’re moving to a supplement outside your one-time open window. We’ll be straight with you about it. Background: what a Medicare Supplement is.
Medicare Advantage is another way to receive your Medicare-covered benefits. These are usually built around a network, so the first question is always whether the doctors you want to keep participate — and that answer is checked one person at a time, not assumed.
This is where Nashville differs from the towns around it. With Vanderbilt, Ascension Saint Thomas and TriStar all operating widely across the city, the question is rarely “is there a doctor near me” and almost always “do the specific people I already see line up.” If you want the structures compared first, start with what Medicare Advantage is and Medicare Advantage versus a Supplement. Neither is automatically the right answer.
Reviewed and approved by Billy Jordan, Jr., licensed agent and President of The Jordan Insurance Agency.
Why work with us
A person with a name and a direct local number. The same person next year, when your prescriptions or your doctors have changed.
Our office is downtown on 4th Avenue North, and you are welcome in it. Most people still choose phone or video — but the option is real, not a mailing address.
Not with a recommendation. What you already have and want to keep is the input, not an afterthought.
Two decades of doing this for families, and a 4.9-star rating across 171 Google reviews.
Nashville service area
The Jordan Insurance Agency helps Medicare clients throughout Nashville and the rest of Davidson County, and in the counties around it. Davidson is one county but a wide one, and Medicare Advantage and Part D availability can vary by county and ZIP code — which is why we check coverage against your actual address rather than the city as a whole. If you live outside the county line, we have pages for Brentwood, Franklin, Hendersonville, Mount Juliet and Murfreesboro as well.
Three ways to do this
Many clients choose this even though we’re in town. One call, your doctor and prescription list in front of you, and we work through it together.
Useful when an adult child wants to sit in from out of town. We can share a screen and walk through the comparison as we go.
You’re welcome at our Nashville office: 159 4th Avenue N, Suite 100, downtown. Appointments preferred so the right agent is expecting you.
Real client experiences
Verified Google reviews of The Jordan Insurance Agency. Individual experiences vary, and these are agency-wide rather than specific to Nashville.
“Billy has provided outstanding service navigating the complex world of Medicare plans! He responds quickly, communicates clearly, and has the utmost patience. He and his team are efficient, kind and always professional.”
“Mr. Jordan patiently walked me through the entire process. The option I chose will save me $200 per month in my premium and it is a better policy than I had previously. I highly recommend Billy Jordan.”
“My experience with Billy was perfect. My husband passed away and I needed individual insurance by year’s end. Billy helped me find the best insurance for my situation — and it’s affordable. Caring, listening, knowledgeable, and professional.”
Go deeper
Medicare guides written by The Jordan Insurance Agency and reviewed by Billy Jordan, Jr., licensed agent.
Good to know
Yes, and Nashville is where our Tennessee office is. We are at 159 4th Avenue N, Suite 100, downtown, and we work with Medicare clients across Nashville and Davidson County. You can handle the whole thing by phone or by video if you’d rather, or come in and sit down.
Yes. Appointments are preferred so the right licensed agent is expecting you and has time set aside. Bring the doctors you want to keep and your prescription list with doses. Most people are done in under an hour.
It can matter a great deal, and in a city where all three operate this widely it is a normal situation rather than an unusual one. If some of the people you see sit in one system and some in another, that is worth mapping out before you choose a path, because the two Medicare structures handle it differently. We check each doctor individually rather than assuming by system.
About three months before your birthday month, when your Initial Enrollment Period opens. Starting then gives you room to check your doctors and prescriptions without rushing a deadline. If you’re still working, your timing may be different, which is worth a short call.
Sometimes, and it depends on your specific situation — including whether you have group health coverage based on your own or your spouse’s current employment. Employer size can also affect how Medicare coordinates with that coverage. Some people can delay Part B without penalty and some can’t, and finding out afterward is expensive. Bring us your plan details before you decide.
Not necessarily. Medicare Advantage and Part D availability can vary by county and ZIP code, so a friend in Brentwood or Hendersonville may not be choosing from the same options you are. It is the reason we check against your actual address instead of treating Middle Tennessee as one market.
Our guidance is free to you, and you will not pay more for a plan by going through a licensed agent than by enrolling on your own. The Jordan Insurance Agency does not charge a separate consultation fee for this Medicare plan review. If you enroll through us, an insurance company may compensate The Jordan Insurance Agency.
People use all three words, and here they lead to the same place. Legally, we are licensed insurance agents. Because we are independent, many people call us a Medicare broker; and because most of what we do is help you think the decision through in plain English, others call us a Medicare advisor. Whichever term you searched, you reach the same licensed, local team — at no cost to you.
Licensed guidance · No pressure
Pick a time that works, or call (615) 558-6082. Bring your doctors and your prescription list — and if the coverage you already have is the right fit, we’ll tell you that too.
North Carolina Office
3540 Toringdon Way
Suite 200
Charlotte, NC 28277
Tennessee Office
159 4th Ave N
Suite 100
Nashville, TN 37219
(704) 926-7565
(980) 206-3356
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