The seven-month window that decides everything
Your Initial Enrollment Period runs seven months: the three months before the month you turn 65, your birthday month, and the three months after. That window is the single most important thing to understand about turning 65, because the decisions inside it are hard to undo and some of the penalties are permanent.
Enrolling late in Part B without qualifying coverage can trigger a late-enrollment penalty that is added to your premium for as long as you have Part B. Not for a year — for as long as you have it. That is why we tell people to map their dates before they start comparing plans.
Still working at 65? Read this part twice
If you are still working and covered by an employer plan, the math changes — and how it changes depends on how many people your employer has. Some people can safely delay Part B. Others cannot, and delaying creates a gap and a penalty.
The single most common misunderstanding we correct: COBRA is not treated as current-employment coverage for Part B special-enrollment timing. People assume COBRA protects them the way an active employer plan does. It does not. If you are on COBRA and approaching 65, talk to someone before you make a decision.
What we actually do in a timing review
- Map your dates. Your Initial Enrollment Period, your employer coverage end date, and any special enrollment window you may qualify for.
- Check whether you can delay. Based on your employer's size and your actual coverage — not a rule of thumb.
- Verify your doctors, hospitals, and prescriptions. By name. Every one of them. Networks in Northern Virginia are genuinely local, and a plan that is strong in Fairfax County can be thin in Loudoun.
- Coordinate a spouse who is still under 65. Two transitions, one plan — they should be planned together, not separately.
- Tell you when to keep what you have. Sometimes retiree coverage or an employer plan is the better option. We say so.
The questions worth answering before you enroll
- When exactly does my Initial Enrollment Period open and close?
- Am I able to delay Part B safely, given my employer's size?
- What happens to my spouse's coverage when I move to Medicare?
- Are my specialists at Inova, VHC Health, or wherever I actually go in network?
- Is every prescription I take covered, at what tier, and at what cost?
- What is my HSA situation once I enroll?
Turning 65 in the next six months?
We will map your enrollment window and verify your doctors and prescriptions — free, with no pressure.
Schedule a Medicare timing reviewWhy people come to us for this
We are an independent agency in Tysons. We represent many carriers rather than one, so a comparison with us is a real comparison. We are allowed to tell you to keep what you already have, and we do that regularly. And you can drive to our office and sit across from the person who wrote your policy.
Once your Medicare decision is settled, we can look at the things that often follow — Medicare Supplement, Part D, dental, vision and hearing, or long-term care planning. Never before. The immediate decision comes first.