Turning 65 Soon? Here’s Your Complete Medicare Checklist
Turning 65 is one of the biggest milestones in your Medicare journey — and it’s also when mistakes can lead to lifetime penalties, higher premiums, or losing access to your doctors.
This simple checklist will keep you on track so you know exactly what to do and when to do it.
Step 1 — Know Your Medicare Enrollment Timeline
Your Initial Enrollment Period (IEP) is a 7-month window:
3 months before your 65th birthday
The month of your birthday
3 months after
This is your penalty-free period to enroll in Part A and/or Part B.
Step 2 — Decide Whether You Need Part B Now
You must enroll in Part B unless you have:
✔ Employer group insurance
✔ Union insurance
✔ Spouse’s active employer insurance
The following DO NOT count as creditable for Part B:
✘ Marketplace/Obamacare ✘ COBRA ✘ Retiree coverage ✘ VA alone
Missing your Part B window can trigger permanent penalties.
Step 3 — Compare Medicare Advantage vs Medigap
This is the most important decision at 65.
Medicare Advantage (HMO/PPO):
Lower cost
Local networks
PPOs allow more flexibility
HMOs require referrals
Medigap + Part D:
Higher monthly premium
Nationwide coverage
No referrals
Predictable costs
Capstone Health helps you compare both options based on your doctors, your medications, and your health needs.
Step 4 — Confirm Your Doctors & Medications
Before enrolling in a plan:
✔ Check your primary doctor
✔ Check your specialists
✔ Confirm your pharmacy
✔ Review your medications
One small mistake can cost hundreds per month.
This is why we run a full doctor + medication review for every client.
Step 5 — Enroll in Your Medicare Plan
Once you’ve reviewed your options, you may enroll in:
Medicare Advantage (HMO/PPO)
Medigap + Part D
Part B only (if continuing employer coverage)
Enrollment is done through Social Security and private carriers. Capstone Health handles the process for you at no cost.
Step 6 — Avoid the Most Common Turning 65 Mistakes
The biggest Turning 65 mistakes include:
Missing your Part B deadline
Choosing a plan because of a “food card”
Not checking specialists
Enrolling through a call center
Relying on TV commercials
Picking a plan without understanding the network
Let us help you avoid these pitfalls.
Ready for Help With Your Turning 65 Medicare Enrollment?