Service

Social Security & Medicare Enrollment

The soup-to-nuts walk-through. The thing nobody else does.

What it is

The plain-English version.

Most insurance agents will sell you a Medicare plan and call it a day. I won't. The process of actually getting onto Medicare — and figuring out when to claim Social Security — is the part where people get tripped up the most.

Filing for Social Security has timing implications that affect the rest of your retirement. Enrolling in Medicare has windows that, if missed, cost you a permanent penalty on your premium. The two systems don't talk to each other, and the rules feel deliberately complicated.

So I help with the whole process — from your Social Security application to your Medicare Part B effective date, to your plan enrollment, to the first time you call about a bill. That's the soup-to-nuts approach.

Who it's for

Probably you, if any of these sound familiar.

  • Anyone within 6 months of their 65th birthday who hasn't started Medicare yet.
  • Folks unsure when to claim Social Security — at 62, full retirement age, or 70.
  • Retiring couples who need to coordinate two Medicare enrollments with two Social Security claiming decisions.
  • Anyone whose spouse is on the working side of an employer health plan that's about to end.
  • People who tried calling Social Security or Medicare and gave up after the third hold.
How I Help With It

In John’s own words.

“We sit down together and lay out a timeline — when to apply for Social Security, when to enroll in Part A and Part B, when each form needs to be in. I tell you exactly what to do, and in what order.”

“When forms have to be filled out, I walk through them with you, signature by signature. I don't just send you a link to ssa.gov.”

“When your Part B effective date is set, I coordinate that with whichever Medicare plan we've picked — Advantage or Supplement — so coverage starts on day one without a gap.”

“And when the first bill or notice arrives that doesn't make sense, you call me. I read these things every day. I'll tell you what to do.”

— John F. Morrison
FAQ

About SS & Medicare Enrollment

When should I start the Medicare enrollment process?
Six months before your 65th birthday. That gives us time to sort out the right plan, the right timing, and any coordination with an employer plan if you're still working.
Should I claim Social Security at 62 or wait?
There's no universal answer — it depends on your health, your other retirement income, your spouse, and your tax situation. We'll walk through your specific case and look at the trade-offs.
What if I'm still working at 65?
If you have credible coverage through your employer or your spouse's employer, you may be able to delay Part B without penalty. But there are rules and exceptions — let's talk through your specific situation before you skip it.
What if I miss a Medicare enrollment window?
There are special enrollment periods for specific circumstances (job loss, moving, etc.). If you've missed a window, call me anyway — there may be a way to get coverage without the late-enrollment penalty. I'll tell you straight.
Related Services

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All six services

Medicare Advantage

Most coverage for the least out-of-pocket — for most of the seniors I talk to.

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Prescription Drug Plans (Part D)

Pairs with Medicare. Picks up where your other coverage stops — at the pharmacy counter.

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Medicare Supplements (Medigap)

When you want predictable costs and the freedom to see almost any doctor in the country.

Read more

Ready to talk? Let’s find 30 minutes.

No pressure. No quotas. I’ll listen, ask a few questions, and if I can help you I’ll tell you how. If I can’t, I’ll tell you that too.

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