Turning 65? Let’s make this simple.
Medicare has four parts, two very different paths, and deadlines that carry permanent penalties if you miss them. Most of what arrives in your mailbox is trying to sell you something rather than explain it.
We’ll walk you through it in about fifteen minutes, show you what each option costs where you live, and handle the enrollment.
TIMING
Your window opens three months before your 65th birthday.
Your Initial Enrollment Period runs seven months: the three months before your birthday month, your birthday month, and the three months after. The earliest you’re able to enroll on a Medicare plan is the first of the month, in the month you turn 65. So for example, if you’re born on June 24th, your Medicare will begin on June 1st.
Still working at 65?
Creditable employer coverage may let you delay Part B without penalty. Whether it counts depends on employer size — getting this wrong is expensive.
Retiring after 65?
Losing employer coverage opens a Special Enrollment Period, tied to the date coverage ends — not the date you retire.
Already on Medicare?
Plans change every year. We review yours against what’s available now, at no charge, whether or not we placed it.
Not sure which of these is you? That’s a two minute phone call. (203) 375-7511
HOW MEDICARE IS BUILT
The parts of Medicare.
A
Hospital
Inpatient stays, skilled nursing, hospice. Free for most people — those with 40 quarters of work history. Otherwise [premium] per month.
C
Medicare Advantage
A private plan bundling A and B, usually with drug coverage included. One of the two paths below.
B
Medical
Doctor visits, outpatient care, labs, equipment. Everyone pays: [premium] monthly, usually deducted from Social Security. Annual deductible [amount].
D
Prescriptions
Drug coverage — built into an Advantage plan, or bought separately alongside a Supplement.
Parts A and B together are called Original Medicare. They cover a great deal, but they have no out-of-pocket maximum — which is why almost nobody stops there.
THE ACTUAL DECISION
Advantage or Supplement. This is the choice that matters.
Which one costs you less depends on your health, your doctors, your prescriptions, and how much predictability you want.
| Medicare Advantage (Part C) | Supplement (Medigap) | |
|---|---|---|
| Monthly premium | Low premium, plus your Part B | [range], plus your Part B |
| Drug coverage | Usually included | Bought separately as Part D |
| Your doctors | Network – HMO or PPO | Anyone accepting Medicare |
| Cost when you use it | Copays up to an annual maximum | Very little, depending on plan |
| Extras | Often dental, vision, hearing | None – medical costs only |
| Changing later | Switch each year during AEP | May require health questions in some states (CT not one of them) |
The trade-off, plainly
Advantage costs less each month and more when you use it. A Supplement costs more each month and much less when you use it. Rarely see a doctor? Advantage often wins. Ongoing conditions or specialists? Usually the Supplement.
The timing point most people miss
For six months after your Part B starts, you can buy any Supplement sold in your state regardless of health. After that window closes, most carriers can ask health questions and decline you, unless you live in a guaranteed issue state like CT.
COSTS
Here’s what you’ll pay. All of it.
Nobody should be surprised by a premium after they enroll. There are four places money comes out, and any honest comparison accounts for all of them.
01
Part A premium
$0 for most people. [amount] monthly without 40 quarters of work history.
02
Part B premium
[amount] monthly at the standard rate. Higher above the income threshold — see IRMAA.
03
Your plan premium
Advantage often low premium. Supplement typically [range] by letter, age, and location.
04
What you pay to use it
Advantage: copays up to [range] a year. Supplement: usually the Part B deductible and little else.
A $0 premium Advantage plan is not free.
You still pay your Part B premium every month, and you pay copays when you use it. We’ll show you both numbers before you decide.
WORTH KNOWING NOW
Two things that cost people money later.
The Part B late enrollment penalty
Sign up late without creditable employer coverage and your premium rises 10% for every full 12-month period you could have had it and didn’t. That penalty is permanent — it stays for as long as you have Part B. The most expensive mistake we see, and entirely avoidable.
IRMAA — the income adjustment
Above a certain income you pay more for Part B and Part D, based on your tax return from two years ago. That catches people in their first year of retirement — charged on income they no longer have. If yours dropped, you can appeal with form SSA-44. Most people don’t know it exists.
IF MONEY IS TIGHT
There are programs for this, and they’re underused.
We can check your eligibility for you. If it looks like you qualify, we’ll help you apply — no charge for that either.
Connecticut runs Medicare Savings Programs that can pay your Part B premium outright, and the federal Extra Help program cuts prescription costs substantially. The income limits are more generous than most people assume, and many who qualify never apply because nobody told them.
Ask us!
(203) 375-7511
We can tell you if you qualify for the Medicare Savings Program. We’ve help many people apply and get approved for benefits they didn’t know they could get.
WHAT TO EXPECT
From first call to enrolled.
A 15-minute call
Your doctors, your prescriptions, what worries you. No forms first.
A side by side
Plans checked against your doctors and drug list, with real monthly and annual costs
We enroll you
We handle the application and the carrier. Effective dates confirmed in writing.
We’re here next year
Claims, ID cards, formulary changes — and an annual review, because plans change.
There’s no charge for any of this. We’re paid by the carrier.
DATES TO KNOW
Enrollment Windows.
Initial Enrollment Period – the seven months around your 65th birthday
Advantage Open Enrollment, Jan 1 – Mar 31 – one chance to switch or return to Original Medicare
Special Enrollment Periods – losing employer coverage, moving, and certain other events
Annual Enrollment, Oct 15 – Dec 7 – change your Advantage or Part D plan for next year
Medigap Open Enrollment – six months from when Part B starts, no health questions
Miss a window and you may be waiting a full year, or answering health questions you’d rather not.
COMMON QUESTIONS
Questions we get constantly.
Do I have to take Part B at 65 if I’m still working?
Not necessarily. Creditable employer coverage usually lets you delay without penalty — but whether it’s creditable depends on employer size and the plan itself. Check before, not after.
Will I keep my doctors?
With a Supplement, yes — anyone accepting Medicare. With Advantage it depends on the network. We check your specific doctors against each plan before you enroll.
Is Medicare Advantage worse than a Supplement?
No. They’re built differently. Advantage has networks and copays but costs less monthly and often includes extras. Supplements cost more monthly with broader access. The right answer depends on you.
What about my prescriptions?
We run your drug list against each formulary and show the annual cost, not just the premium. Two plans with identical premiums can differ by thousands.
Does this cost me anything?
No. Our help is free. Carriers pay us, and not differently depending on which plan you pick.
Do you handle dental and hearing?
Yes — standalone dental and vision plans, and hearing benefits. Many Advantage plans include some of this; where they don’t, we place separate coverage.
BOOK A CONSULTATION
Tell us what you need. We’ll do the rest.
Fill out our form and we’ll contact you shortly, usually within 24 hours. If you prefer, you can also call us or text us at (203) 375-7511. We look forward to talking with you!
HOURS
Weekdays: 8:00 AM – 5:00 PM
Weekends: By Appointment Only
Medicare Disclaimer: We do not offer every plan available in your area. Any information we provide is limited to the plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options. Licensed in CT, SC, FL, NJ.