Turning 65 · Medicare next steps
Turning 65? Make a clear plan for Medicare.
You don’t have to figure it all out at once. Talk with Toby Ferguson about enrollment timing, employer coverage questions and the choices ahead—starting with your situation.
Read the free turning-65 checklist ↓No sign-up needed for the checklist. No obligation to enroll.
Toby Ferguson
Independent Life & Medicare Agent · CA license 0C11736
Based in Ontario. Helping neighbors in Upland, Rancho Cucamonga, Chino and nearby Inland Empire communities.
Get to know Toby →Let’s plan your next steps.
Request a timing conversation. Tell Toby how to reach you, and arrange a time that works for you.
A conversation, at your pace
A little preparation. A clearer path forward.
Start with a timing conversation
Tell Toby whether you’re approaching 65, still working or preparing to retire. Bring the questions you already have.
Understand what to check
Discuss your enrollment timeline and the questions to confirm with Social Security or your employer’s benefits administrator.
Plan a coverage consultation
When you’re ready, arrange a fuller conversation about available coverage, your doctors, prescriptions and costs.
Keep this handy
Your turning-65 preparation checklist.
Six things to think through before choosing coverage. Read it now, bookmark it, or print this page from your browser.
Still working past 65?
Your employer coverage and HSA can affect the steps you need to take. Ask for an individual timing review before deciding to delay Medicare.
Ask Toby about your timing →Start with your timing
Write down when you expect to need Medicare. If you are retiring, include when your employer coverage will end. You do not need to share your full birth date to request help.
Check your current coverage
Ask your benefits administrator how your coverage works with Medicare. Bring questions about employer size, prescription coverage, retiree coverage or COBRA.
Ask about your HSA
If you or your employer contribute to a Health Savings Account, discuss Medicare enrollment and contribution timing before making changes.
Know what matters to you
Make a private list of your doctors, medicines, preferred pharmacies and budget questions for the appointment. Keep medical details out of the website form.
Understand the coverage choices
Ask about Original Medicare, Medigap and Part D, and how these differ from Medicare Advantage. Compare access to care and total costs, not just premiums.
Confirm your next steps
Find out whether you need to sign up for Part A and Part B, which enrollment periods apply, and when coverage would start before ending existing insurance.
Know your window
Your first Medicare enrollment follows your own timeline.
For most people, the initial enrollment period includes the three months before the month they turn 65, their birthday month, and the three months after. Your situation can change the timing, including a birthday on the first of the month or coverage through current employment.
Confirm your dates before making coverage changes. Turning 65 and fall Annual Enrollment are different situations.
Check enrollment timing at Medicare.gov ↗Before we talk
A few questions you may have.
Toby comes to you for in-home appointments, or meets by phone and video across California, Nevada and Arizona.
Plan my Medicare next stepsHow early should I ask for help?
You can start a conversation several months before you expect to need Medicare. That gives you time to check employer benefits and understand your individual enrollment steps.
Do I automatically get Medicare at 65?
Some people are enrolled automatically, while others need to sign up. Check your status with Social Security rather than assuming coverage has started.
Can I keep working and delay Medicare?
It depends on your circumstances, including your current employer coverage. Check with your benefits administrator and get individual guidance before delaying enrollment. HSA contributions need a separate timing check.
Do I need to give you my Medicare number?
No. The initial request only needs basic contact information and your ZIP code. Do not send Medicare numbers, Social Security numbers or medical details through this form.