The Turning 65 Newsletter · Issue No. 1
Medicare Made Clear: what to do in the year you turn 65
Three things trip people up at 65: the timing, the penalties, and the choice between Medicare Advantage and a Medicare Supplement. Here's each one in plain English — from a licensed independent agent, at no cost to you.
Written by ShaDonna Stubbs · Custom Insurance Solutions
1. Your turning-65 roadmap
Medicare rewards people who start early. Here's the sequence that keeps you out of trouble.
- 01
6 months before your birthday
Take inventory
Write down your doctors, your prescriptions (name, dose, frequency), and your pharmacy. Nearly every Medicare decision comes back to this list. If you have a Health Savings Account, note that HSA contributions must stop before Part A begins.
- 02
3 months before your birthday month
Your Initial Enrollment Period opens
This is a 7-month window: the 3 months before your birthday month, your birthday month, and the 3 months after. Enrolling in the first 3 months is best — coverage then starts the first day of your birthday month.
- 03
Still working?
Check your employer coverage first
If you (or your spouse) have active group coverage from an employer with 20 or more employees, you may be able to delay Part B without a penalty and use a Special Enrollment Period later. Fewer than 20 employees usually means you should enroll on time. Confirm with your benefits administrator in writing.
- 04
2 months before
Choose your path
Original Medicare plus a Medigap plan and a Part D drug plan — or a Medicare Advantage plan. Medigap has a one-time open enrollment window that starts when your Part B begins; more on that below.
- 05
Birthday month
Coverage begins
Confirm your cards arrived, your doctors show as in-network, and your medications appear on your plan's formulary at the tier you expected.
- 06
Every fall, October 15 – December 7
Review, don't autopilot
Plans change their drug lists, networks, and costs every year. An annual review is how people find savings — and how they avoid surprises in January.
2. The penalties nobody warns you about
Most Medicare late penalties aren't one-time fees — they're added to your premium for life. All of them are avoidable with a phone call before you decide.
The Part B late penalty is permanent
If you don't sign up for Part B when first eligible and you don't have qualifying coverage from active employment, your premium goes up 10% for each full 12-month period you could have had it. That increase stays with you for as long as you have Part B.
The Part D penalty is small — and forever
Go 63 or more days in a row without creditable prescription coverage and a penalty is added to your Part D premium, calculated from the national base premium and the number of months you went without. It's a few dollars a month, but it never goes away.
COBRA and retiree plans are the classic trap
COBRA and most retiree coverage do not count as active employer coverage for delaying Part B. People assume they're covered, then discover a penalty and a coverage gap. If you're leaving a job near 65, ask before you decline Part B.
Missing your Medigap open enrollment
You get a one-time 6-month Medigap open enrollment period that begins the month your Part B starts and you're 65 or older. During it, you can buy any Medigap plan sold in your state regardless of health history. After it ends, most states let insurers use medical underwriting — a health condition can mean a higher price or a decline.
3. Medicare Advantage vs. Medigap
There is no universally better answer — there's the one that fits your doctors, your medications, your travel, and your budget. Here's the honest comparison.
| Medicare Advantage (Part C) | Medigap + Part D | |
|---|---|---|
| Monthly premium | Often $0 beyond your Part B premium | A monthly premium in addition to Part B |
| Doctor access | Plan network — HMO or PPO rules apply | Any provider in the U.S. who accepts Medicare |
| Costs when you use care | Copays per visit, with an annual out-of-pocket maximum | Little to nothing at the point of care, depending on plan letter |
| Referrals & prior authorization | Common, varies by plan | Not used |
| Drug coverage | Usually built in | Bought separately as a Part D plan |
| Extras (dental, vision, hearing, fitness) | Frequently included | Not included; can be added separately |
| Switching later | Can change each fall | May require medical underwriting after your open enrollment window |
A simple way to think about it
Medicare Advantage generally trades a lower monthly premium for copays and a network. Medigap generally trades a higher monthly premium for predictable costs and freedom to see any provider who accepts Medicare. If you travel often, split time between states, or see specialists at multiple health systems, that freedom matters more. If you're healthy, budget-focused, and happy with local doctors, Advantage can be a strong fit.
Your next step
Bring me your doctor list and your prescriptions.
We'll run your medications through the drug lists, check your doctors against networks, and compare what's actually available where you live. There's no fee to work with us — carriers compensate agents directly.
This newsletter is general education, not individualized advice, and rules and plan details change. Costs, penalty amounts, and enrollment rules are set by Medicare and can be confirmed at Medicare.gov or 1-800-MEDICARE. We do not offer every plan available in your area.