Medicare: Your Turning 65 Checklist

✅ FREE CHECKLIST

Turning 65? Here’s Your Medicare Action Plan

Simple checklist: what to do 6 months before, 3 months before, and the month you turn 65 – so you don’t miss anything or pay penalties

Medicare has strict deadlines. Miss them and you’ll pay penalties for the rest of your life. Or go months without coverage.

We created a simple one-page checklist that shows you EXACTLY what to do and when – step by step.

What’s in the checklist:

📅 6 MONTHS BEFORE TURNING 65

• Learn the 4 parts of Medicare (A, B, C, D)
• Decide: enroll at 65 or delay
• Compare coverage options
• Estimate your monthly costs

📅 3 MONTHS BEFORE TURNING 65

• Apply for Medicare Parts A & B at ssa.gov
• Check your application status
• Choose: Supplement + Part D or Advantage
• Consider dental, vision, hearing coverage

📅 THE MONTH YOU TURN 65

• Receive your red, white & blue Medicare card
• Create your account at MyMedicare.gov
• Get all plan ID cards
• Cancel old insurance (if needed)

📅 ANNUALLY (EVERY FALL)

• Review your Annual Notice of Change
• Compare plans during AEP (Oct 15 – Dec 7)
• Check prescription and provider coverage
• Shop for better Medigap rate

Why this checklist works:

📋 ONE PAGE

Print it and stick it on your fridge. Everything important in one place. No 50-page guides.

⏰ CLEAR DEADLINES

Know exactly when to do what. No surprises, no missed deadlines.

✅ SIMPLE ACTIONS

Each item is a specific action with a checkbox. Check it off and move on.

Who created this checklist

Veronika Rowell
Founder & Principal Agent, Chief Insurance Services
PhD in Economics • Licensed Insurance Agent • Social Security Registered Analyst

Veronika is a former university professor who brings an educator’s approach to Medicare and health insurance. Instead of pushing plans, she breaks down complex topics, from Medicare Supplement vs. Medicare Advantage to Part D drug coverage and Social Security coordination, so you actually understand your options before making a decision.
With a PhD in Economics and years of teaching experience, she founded Chief Insurance Services to give people what’s missing in the insurance industry: clear, unbiased guidance without the sales pressure.
Together with her bilingual team of licensed agents, she has helped thousands of families nationwide find the right coverage, avoid costly mistakes, and make informed decisions about their healthcare and retirement benefits.

⭐⭐⭐⭐⭐ 300+ Google reviews
📍 Licensed in all 50 states
🗣️ Bilingual support available

Download your free checklist


🔒 We never share your information with third parties. No spam.
📥 Over 500 people have downloaded this checklist.

What our clients say

Ugis Levensteins
Ugis Levensteins
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Nadja is great consultant.
She took care of all my needs and interests about Medicare. I really suggest her to everybody.
Milla Way
Milla Way
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I had a great experience with this team while getting started with Medicare. Nataliia K. was extremely helpful, answered all my questions, and showed outstanding professionalism. She was very patient and supportive, which made the process much easier for me.
Alec Dee
Alec Dee
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Very knowledgeable, customer oriented and friendly.
Great overall experience!

Frequently Asked Questions

When should I start preparing for Medicare

Ideally, 6 months before you turn 65. This gives you enough time to learn your options, compare plans, and make an informed decision without rushing.

What happens if I miss enrollment deadlines?

It depends on which deadline you miss. Missing Part B can mean a 10% penalty for each year you were late – for life. Missing Part D means a 1% penalty for each month without coverage – also for life.

I'm still working and have employer coverage. Do I need Medicare at 65?

Not necessarily. If you have “creditable coverage” from an employer, you may be able to delay Medicare without penalties. But it depends on company size and coverage type. Best to check with us – it’s free.

Is the checklist really free? What's the catch?

No catch. We’re licensed insurance agents. Our services are free to you because insurance companies pay us. The checklist is a way to introduce ourselves and show we can help.

Have questions right now?

📞 Call us: 616-600-8444
📅 Or book a free consultation

Chief Insurance Services
2828 Kraft Ave SE #104, Grand Rapids, MI 49512
Licensed Insurance Agency

We are not connected with or endorsed by the United States government or the federal Medicare program.