You're at a crossroads.

We know the way.

Whether you're approaching retirement, navigating a disability, a veteran, or managing benefits for your team — Senior Street Advisory provides honest, clear guidance. Find your situation below.

Who We Serve

Retirees & Pre-Retirees

You've worked hard your entire life. The last thing you should have to navigate is the most confusing benefits system in America — alone, on a deadline, with permanent consequences for getting it wrong.

Sound familiar?

"I'm turning 65 in three months. My inbox is full of Medicare mailers I don't understand, my HR department says I need to act, and every time I research online I get more confused. I don't want to make a mistake I can't undo."

What you're actually dealing with

Permanent penalties for missing enrollment deadlines
Medicare's Initial Enrollment Period is just 7 months. Miss it, and you face a 10% Part B penalty — every year, for the rest of your life. Part D drug penalties add another 1% per month with no cap.
The COBRA trap
Many people buy COBRA after leaving a job thinking they have time. What they don't know: COBRA does not pause your Medicare enrollment window. When COBRA ends, they can be left with gaps — and penalties.
Medicare Advantage vs. Supplement paralysis
Both options have real trade-offs. Advantage plans have lower premiums but narrow networks and out-of-pocket maximums up to $9,250. Supplements cost more monthly but protect you from large bills. The right answer depends on your health, doctors, and budget.
Drug coverage surprises when plans quietly change formularies each year
A medication that cost $30 last year can jump to $300+ when a plan quietly drops it from its formulary. Annual plan reviews aren't optional — they're essential.

How SSA Guides You

Enrollment timeline review
We identify your exact enrollment windows before they close — no penalties, no surprises.
Plain-English plan comparison
We compare Advantage vs. Supplement using your actual doctors, medications, and budget.
Annual drug plan audit
We review your Part D plan against your current prescriptions every fall before the enrollment window closes.
Employer-to-Medicare transition
We coordinate the timing of leaving group coverage so you never face a gap or a preventable penalty.
Enrollment handled alongside you
We walk through the process with you so nothing gets missed.

Not sure which category fits you?

That's exactly what we're here for. Tell us your situation and we'll help you figure out where you stand — and what to do next. No obligation, no pressure.