The answer turns on two questions, not one

Turning 65 while you are still working is normal in Nashville, and so is the confusion that comes with it. The honest answer to whether you have to take Medicare depends on two specific things: whether you or your spouse are still actively working, and how many employees that employer has. Everything else — how good the plan is, how much you like it, how long you have had it — is secondary to those two facts.

The distinction that catches people out is between coverage from a job somebody currently holds and coverage that traces back to a job somebody used to hold. Medicare treats those two completely differently, even when the insurance card looks identical.

Part A at 65, and the HSA trap

Part A is premium-free for most people with 40 or more quarters of work history — $0 a month in 2026 — so many people take it at 65 even while they keep working and keep their group plan. With a shorter work record Part A carries a premium: $311 a month with 30 to 39 quarters, and $565 a month with fewer than 30, which changes the calculation.

There is one real exception, and it matters to a lot of working people. If you contribute to a Health Savings Account, you and your employer have to stop contributing once any part of Medicare starts, including premium-free Part A. Enrolling in Part A after 65, or starting Social Security, can also make Part A retroactive to an earlier date, which can turn contributions you already made into a problem. If an HSA is part of your plan, stop contributions ahead of time and confirm your exact dates before you file anything.

The 20-employee rule is the one that decides Part B

Part B carries a premium for everyone — $202.90 a month in 2026, with an annual deductible of $283, and more than that for higher earners once modified adjusted gross income passes $109,000 for one person or $218,000 for a couple filing jointly. Whether you should be paying that while you are still covered at work depends on the size of the employer providing the active coverage.

Employers with 20 or more employees

  • The group health plan generally pays first and Medicare pays second.
  • You can usually delay Part B without a penalty while you or your actively working spouse stay covered by that plan.
  • An 8-month Special Enrollment Period opens when the employment ends or the group coverage ends, whichever happens first. The clock starts then. It does not restart later when a COBRA extension runs out, which is the single most expensive misunderstanding in this whole subject.
  • You do not have to wait for that window. You can also take Part B at any point while you are still working and covered.

Employers with fewer than 20 employees

  • Medicare typically pays first and the group plan pays second.
  • Because of that, people in this situation usually need both Part A and Part B at 65. Skipping Part B can leave large bills uncovered, because the small-group plan is built on the assumption that Medicare is already paying as the primary coverage.
  • Confirm in writing with the plan's benefits administrator how it coordinates with Medicare before you delay anything. A verbal reassurance from a busy office is not worth what it costs if it turns out to be wrong.

From a paycheck, small-employer coverage and large-employer coverage feel identical. To Medicare they are not remotely the same, and that gap between how it feels and how it works is where most of the damage happens.

COBRA and retiree coverage are not active employer coverage

This is where good, careful people get hurt. COBRA lets you keep a former employer's plan going for a period after you leave, but for Medicare purposes it is not coverage based on current employment. Neither is retiree coverage. In practice that means:

  • Neither one gives you a Special Enrollment Period that lets you delay Part B without a penalty.
  • If you are already 65, your Initial Enrollment Period still applies even though you also have COBRA or retiree benefits — the clock does not pause.
  • Waiting until COBRA ends to take Part B can leave you with both a coverage gap and a permanent surcharge — see how the Medicare late enrollment penalty works.

One exception worth knowing: COBRA's disability extension runs about 29 months, which can bridge most or all of the 24-month wait faced by people who come to Medicare through Social Security Disability Insurance. That is a genuinely useful bridge, and it matters more in Tennessee than it would in a state that expanded Medicaid, because there is less underneath it if the bridge is not there.

Do not forget the prescription side

Your employer plan's drug benefit is its own separate question. Plan sponsors send a notice each year saying whether their drug coverage counts as creditable prescription drug coverage. If it does, the months you spend on that plan do not work against you later. If it does not, a surcharge can accumulate quietly while you are still happily at work. Keep the notices, and read what Medicare Part D covers in Tennessee before you assume your group plan has you handled.

When you do retire, the network question arrives

Here is where Tennessee gets specific. Nashville is served widely by three large health systems — Vanderbilt, Ascension Saint Thomas and TriStar — and a generous employer plan often lets a household use two of them without thinking about it. A primary care doctor at one, a cardiologist or an orthopedist at another. The moment you move off that employer plan, those relationships stop being automatic and start being a network question. Some people answer it by staying with Original Medicare and a supplement; others answer it by checking each doctor against a specific Medicare Advantage plan's network in Tennessee. Neither answer is the right one in general; only one of them is the right one for your household.

Where you live decides what is even on the table. Medicare Advantage and Part D availability can vary by county and ZIP code, so the options for someone retiring in Brentwood or Nolensville are not necessarily the options for someone retiring in Gallatin, Mount Juliet or La Vergne — even when they worked at the same company in Nashville. Our Medicare page for Nashville covers how we work across Davidson, Williamson, Sumner, Wilson and Rutherford counties, and our guide to when you can enroll in Medicare in Tennessee lays out every window in order.

How The Jordan Insurance Agency helps

We start with the two questions that decide everything: who is actively working, and how big that employer is. From there we get the dates in writing, work out whether delaying Part B is genuinely safe for you or only feels safe, and plan the handoff for the day the job ends — including the drug coverage, which is the piece people forget until it has already cost them something.

The Jordan Insurance Agency is an independent, licensed insurance agency with a Tennessee office at 159 4th Avenue N, Suite 100, Nashville, TN 37219. You can reach us at (615) 558-6082, Monday through Friday, 8:00 AM to 4:00 PM Central. Because we are independent we represent multiple carriers rather than one, so we can lay your real options side by side instead of steering you toward a single company. A consultation with a licensed agent is free, and your premium is the same whether you enroll on your own or with our help.