Turning 65?
Don't Miss a Single Deadline.
Medicare enrollment has strict windows — and missing them can cost you permanently. This free checklist walks you through every step, in the right order, so nothing slips through the cracks.
If you miss your Initial Enrollment Period and don't have other qualifying coverage, Medicare can charge you a 10% premium increase for every 12-month period you were late — and that penalty follows you for life.
Your free checklist covers:
- Your exact enrollment window and when the clock starts
- The 4 parts of Medicare and what each one actually covers
- Medicare Supplement vs. Advantage — how to know which is right for you
- Documents to gather before you enroll
- 7 costly mistakes first-time enrollees make — and how to avoid every one
The Mistakes That Cost People the Most
Medicare enrollment isn't forgiving.
Most people spend more time researching a new TV than they do their Medicare coverage. These are the three mistakes that follow people for years.
Your Initial Enrollment Period is 7 months long and only happens once. Missing it means waiting — and paying a permanent penalty on your monthly premium for as long as you have Medicare.
Medicare Supplement and Medicare Advantage work very differently. Picking the wrong one based on the monthly premium — without understanding the full cost picture — is the most common regret.
Some employer plans qualify as creditable coverage; many don't. Assuming yours does — without verifying — is a mistake that can trigger the late enrollment penalty even when you didn't realize you owed it.
Inside Your Free Checklist
Everything in one place. Nothing missing.
Designed for people who want a clear, step-by-step reference — not a 60-page manual full of government jargon.
Your 7-month Initial Enrollment Period mapped out clearly, plus Special Enrollment Period rules if you have employer coverage.
What each part covers, what it costs, and whether you need all four — in plain English, not government terminology.
A side-by-side breakdown of how both plan types work, who they're right for, and the questions to ask before you decide.
A checklist of exactly what to have ready — Medicare card, Social Security info, current prescriptions, and your doctor list.
The most common enrollment errors — including the ones that result in permanent premium penalties — and exactly how to sidestep them.
The 10 questions every Medicare enrollee should ask — whether they're working with an agent, shopping online, or calling Medicare directly.
Ready for your checklist?
Download it free. Reference it any time. Share it with your spouse. It's yours to keep.
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Your Enrollment Timeline
The 7-month window you need to know
Your Initial Enrollment Period starts 3 months before your 65th birthday and runs for 7 months total. Here's how it breaks down.
This is the ideal time to enroll. Coverage begins on the first day of your birthday month, giving you no gap in protection. Start comparing plans now so you're not rushed.
If you enroll during your birthday month, coverage starts the first of the following month. Still time to enroll without penalty — but don't wait much longer.
You can still enroll up to 3 months after your birthday month — but your coverage start date will be delayed. Enroll by month 1 after your birthday for coverage starting 2 months later, and so on.
Miss the 7-month window without qualifying coverage and you'll face a permanent 10% premium penalty for every 12 months you were eligible but didn't enroll. This never goes away.
Johnny Closer is a Florida-based insurance agent focused on helping individuals and families make confident, informed coverage decisions without the confusion. Known for a straightforward approach and dependable service, Johnny works to simplify the process and provide guidance that feels personal, practical, and clear.
What Clients Say
People just like you — who figured it out.
"I had no idea there was a permanent penalty for enrolling late. No one told me! This checklist caught it before I made a very expensive mistake. I shared it with my sister who's also turning 65 this year."
"My employer told me my insurance would 'carry over' to Medicare automatically. It doesn't. This checklist was the first place I saw that explained how the employer coverage rules actually work. Saved me from a big assumption."
"I downloaded the checklist and ended up going through it with my husband over coffee. We both learned things we didn't know. And then we booked a call with the agent afterward — easiest decision we made all year."
Get your free checklist now.
It takes 30 seconds to download. It could save you from a penalty that lasts a lifetime.
Free download · No credit card · Unsubscribe anytime