Free Resource
The Medicare Dude Turning 65 Checklist
A practical checklist to help you navigate Medicare enrollment when you turn 65 — covering every decision you need to make and when to make it.
Written by
William Gray
Founder, The Medicare Dude · Independent Medicare Broker · Licensed Since 1998
Reviewed for accuracy:
Turning 65 is one of the most important Medicare decision points of your life. Your Initial Enrollment Period (IEP) is a 7-month window — 3 months before your birthday month, your birthday month, and 3 months after. Missing it can mean permanent premium penalties and coverage gaps. This checklist covers every step.
Social Security & Medicare Timing
- Confirm whether you are already receiving Social Security benefits (if so, Part A and Part B enrollment may be automatic)
- If not yet receiving Social Security, contact Social Security to enroll in Medicare Part A and Part B separately
- Verify your Medicare card arrives and your effective dates are correct
- Understand that Part A (hospital) is usually premium-free; Part B (outpatient) has a monthly premium
Employer Coverage Questions
- Determine whether you or your spouse still has active employer coverage
- If you have creditable employer coverage, you may be able to delay Part B without penalty
- Confirm with your HR department whether your employer plan is 'primary' or 'secondary' to Medicare
- Understand your Special Enrollment Period (SEP) when employer coverage ends
- Do NOT assume employer coverage automatically transitions to Medicare — confirm the details
HSA Considerations
- Stop contributing to your Health Savings Account (HSA) at least 6 months before enrolling in Part A
- Part A enrollment can be backdated up to 6 months — this can create unexpected HSA contribution penalties
- You can still use existing HSA funds after enrolling in Medicare — you just cannot contribute new funds
Medigap Open Enrollment Period
- Your Medigap Open Enrollment Period (OEP) begins the month you are both 65 and enrolled in Part B
- During your OEP, you have guaranteed issue rights — carriers cannot deny you or charge more based on health
- Your OEP lasts 6 months and does NOT repeat — missing it means future Medigap applications may require medical underwriting
- Compare Plan G and Plan N options during your OEP — this is the best time to lock in coverage
- Call William to compare Medigap options from the carriers he represents before your OEP closes
Part D Drug Coverage
- List all your current prescription medications (name, dosage, frequency)
- Compare Part D plans using Medicare's Plan Finder tool at Medicare.gov
- Enroll in a Part D plan during your IEP to avoid the late enrollment penalty
- Confirm your preferred pharmacy is in-network for the plan you choose
- Review your Part D plan annually during Open Enrollment (Oct 15 – Dec 7) — formularies change
Doctors & Prescriptions
- Confirm your primary care physician accepts Medicare
- Confirm your specialists accept Medicare
- With a Medigap plan, you can see any Medicare-accepting provider nationwide — no network restrictions
- With Medicare Advantage, confirm your doctors are in-network before enrolling
Retirement Date & Coverage Gap
- Identify your exact retirement date and when your employer coverage ends
- Coordinate your Medicare effective date to avoid a gap in coverage
- If retiring mid-month, confirm whether your employer coverage ends at the end of that month
- Plan your Medigap application timing to align with your Part B effective date
Travel & Lifestyle
- If you travel frequently, consider a Medigap plan — it covers you at any Medicare-accepting provider nationwide
- Some Medigap plans (Plan G) include foreign travel emergency coverage
- Medicare Advantage plans are generally limited to a service area — review coverage before traveling
Questions to Ask William
- Which Medigap plan fits my doctors, prescriptions, and budget?
- Which carriers do you represent in my area?
- What is the rate history for the carriers you recommend?
- Should I choose Plan G or Plan N given my health situation?
- How does my employer coverage affect my Medicare enrollment timeline?
- What happens to my coverage if I move after I enroll?
Ready to work through this checklist with William?
William can walk you through every item on this checklist, compare Medigap options from the carriers he represents, and help you avoid the most common turning-65 Medicare mistakes — at no cost and no obligation.
No call centers · No pressure · No cost
Compare Medigap Plans Before Your Open Enrollment Closes
Your Medigap Open Enrollment Period is a one-time window. William can help you compare Plan G, Plan N, and other options from the carriers he represents — before it closes.
Prefer to talk? Call William — 1-800-DUDE-309 (800-383-3309)
Licensed in multiple states · Independent · No cost to you