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Clearing the Hazy Maze of Medicare, Nimble Notes When Working Beyond Age 65

by | Jan 25, 2023 | Insights, Medicare Enrollment

Be Aware, You Are Targeted:

Six months before turning 65, your demographic data might be attached to a report known as, T65. This allows insurance companies, of various sizes, to seek and find prospects so they may “sell” you something.

Good to know: There are two strategies that can augment original Medicare, *Parts A,B,D.

The first, as seen on TV, Advantage plans, are a bit complex as annually, designs change (which adds to the confusion). Enhanced extras like Over-the-Counter allowances, gym memberships and possibly minor dental may entice your enrollment. Beware: some salespeople may push Advantage plans as commissions are higher. Albeit these programs are decent, know their pitfalls and prepare for them.

The second, not often seen on TV, Supplemental programs fill the “gaps” where original Parts A and B leaves you open to liability. This path may be a superior financial strategy depending on your personal situation. These types of policies are “lettered” and provide the same framework of care, year after year. Purchasing a separate drug plan is a must.

You will not need to enroll in the above strategies if you continue to stay enrolled on your employer-based health coverage.

Working Beyond 65, What To Do:

When working beyond 65, you should know there is interplay between employer-based coverage and original Medicare (*Parts A; B; D).

1. The size of your employer matters.

Smaller organizations with less than 20 W-2’d employees, Medicare can become the primary payor when coordinating your care with employer-based coverage. Employers with more than 20 W-2’d, your group policy pays first and Medicare will become secondary.

Most active employees who remain attached to group offerings enroll in only *Part A, which could lower your group deductible exposures should hospitalization claims occur (yet primacy matters).

2. You may delay your Part B and D enrollment because your medically necessary services and prescription coverages are currently provided through your employer-based program. While in an employer-sponsored health care plan, you are in a protected class (thus late enrollment penalties will not occur).

Upon leaving your group policy, this is when you will need to align your Part B enrollment and decide which “strategy” that will augment original Medicare.

3. Take heed, the type of plan you are offered through your employer matters. Health Savings Accounts and Medicare do collide. IF you are enrolled in a Health Savings plan and enrolled in original Medicare Parts A, B, D (one or a combo of any) your tax favored contributions are no longer valid. Please talk with your tax professional to seek further guidance.

Where Do I Go to Enroll in Medicare?

Oddly enough, beginning your initial enrollment into original Medicare (Parts A; B) starts at the Social Security Administration. Website access,, has just gotten easier (redesigned website was just launched, 2023). You may start this process as early as three months before your 65th birthday.

Wise advice: Seek guidance early from your trusted professional circle. There are many moving parts and pieces to your personal Medicare equation. Talking often with knowledgeable local experts may optimize your planning (and comfort).

*Original Medicare Refresher:

Part A: Hospital and Hospice insurance you have been pre-paying via payroll taxes your entire working career.

Part B: Medical insurance (medically necessary and preventive care) you will be required to purchase if you do not have employer-based coverage. Higher premiums occur if you had elevated income two year prior to enrollment.

Part D: Drug coverage you are required to purchase in order to avoid penalty.

Written by

Andi Dolan 


Andi Dolan, founder of Traverse Benefits, a locally owned independent insurance agency providing health, life and disability insurance solutions for individuals, employers and Medicare beneficiaries across Northern Michigan.

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